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Not so long ago, it seemed to Rudolph W. Giuliani that he would be presiding over a hefty part of the world.

Holding court a few nights after the 2016 election in a private cigar bar on Fifth Avenue, glass of Macallan at hand, Mr. Giuliani boasted to friends that President-elect Donald J. Trump would soon nominate him to the most prestigious of cabinet posts.

“How about,” Mr. Giuliani asked, “secretary of state?”

Chief global representative of the United States in war, peace and trade.

It would be a sublime reward for having thrown in with Mr. Trump when the respectable Republican establishment was keeping its distance, a fresh burst of stardom in a public life that had been fading fast. Mr. Giuliani made himself indispensable to the Trump campaign by doing dirty work that no one else wanted and trudging ahead even after the candidate lashed him with humiliations.

Three years on, Mr. Giuliani never got the job he believed he had coming — “a bitter disappointment,” his now-estranged wife says — but in his five decades as a public figure, he has never been more prominent in national affairs.

Step by step, he has escorted President Trump to the brink of impeachment. Mr. Giuliani himself is now under criminal investigation by federal prosecutors in the very office where he enjoyed his first extended draughts of fame nearly four decades ago. The separate troubles he has gotten his client and himself into are products of the uniquely powerful position he has fashioned, a hybrid of unpaid personal counsel to the president and for-profit peddler of access and advice.

Practically no name, other than Mr. Trump’s, was mentioned more than Mr. Giuliani’s at the impeachment hearings and in a subsequent Democratic report that described him as the hub of a grievous abuse of presidential power (or legitimate advocate for Mr. Trump, in the Republicans’ minority response).

A dozen witnesses testified over five days, and if Mr. Giuliani were somehow subtracted from their stories, there seems to be no one in or out of government who could take his place as the president’s man on the ground. No one to carry out a campaign to force a vulnerable ally, Ukraine, to damage a political opponent of Mr. Trump and undermine a special counsel investigation in ways that would help both Mr. Trump and an ally now in prison for laundering millions of dollars.

No impeachment train, picking up steam.

Mr. Giuliani has been the voice in Mr. Trump’s ear when others could not be heard, and served as the voice of Mr. Trump in places where presidents dare not go.

Each modern impeachment saga — of Richard M. Nixon, Bill Clinton and now Mr. Trump — has been shaped not by grievances over policy differences, but by human vanities and appetites. In this case, those include Mr. Giuliani’s, which have run in strong currents for decades, unconcealed.

The forces that have returned Mr. Giuliani to the stage at age 75 are the same ones that made him a star federal prosecutor as a young man, a memorable mayor of New York in the 1990s and a scorched-earth advocate for Mr. Trump in 2016: his relentless drive to put himself at the center of public life and his very high regard for his own virtuousness.

Patrick Oxford, a former law partner and chairman of Mr. Giuliani’s 2008 presidential campaign, who praises him as “a fine man,” says he has not changed.

“He’s just a whole lot more of what he was,” Mr. Oxford said. “I’ve noticed that political figures have a hard time retiring from the scene. I think my friend Rudy may be trying too hard to remain involved.”

[Watch a special episode of “The Weekly” about Rudy Giuliani’s wild, decades-long career. Available for Times subscribers in the U.S.]

His personal life has descended into the sort of well-appointed shambles that material wealth can disguise, though not necessarily make any less fraught.

A third marriage has fallen into divorce court ruins, revealing monthly expenses of $230,000 for six homes and 11 country club memberships. By taking President Trump as a client, he lost a position at a law firm in 2018 that paid him $6 million annually, according to court filings. In October, he broke with a partner in a security consultancy, a former police officer who had been at his side for three decades. He was so badly hurt in a fall two years ago that his wife put off divorce plans and looked after him for a while. She laments that before he appears in public, no one tells him that dye has given his hair an orange tinge.

He betrays no distress at any aspect of his life, only delight.

Working on a laptop at a restaurant table in the Trump International Hotel in Washington, he has bathed in the warm acclaim of friends and strangers who recognize him from his television advocacy. “I enjoyed the fact that people were coming by and tapping me on the back,” Mr. Giuliani said.

He was there so often, he said, that he set up a plaque.

Rudolph W. Giuliani

Attorney at law

“He doesn’t just like the spotlight,” his estranged wife, Judith Giuliani, said in an interview. “He craves it, for validation.”

She said she could scarcely believe he was working for Mr. Trump, given his disdain for people like Mr. Clinton, whom he saw as dishonest. But public attention, even refracted through Mr. Trump, was irresistible, she said.

Perhaps that helps explain the velvet-glove treatment he lavished on two Soviet-born American businessmen.

Mr. Giuliani brought one of them, a former penny-stock trader with a string of bad debts, to the state funeral of President George H. W. Bush last December.

And both men were Mr. Giuliani’s guests this year at an annual dinner he gives for a band of people, mostly city workers, knitted together after the Sept. 11 attacks.

Other guests were perplexed by the men’s presence.

Had they been at Ground Zero in 2001?

No, they had not.

They were part not of Mr. Giuliani’s past but of his wished-for future.

He deployed both men to find pressure points in Ukraine, and joined them in undermining an American ambassador. His intentions, he says, were pure. “As a person who finds public corruption a cancer,” Mr. Giuliani said, “I cannot ignore it.”

He may also have been trying to improve the chances for Rudolph W. Giuliani to persist into his ninth decade as an indispensable man.

The Thanks He Got

Poised to take off from La Guardia Airport, the Trump campaign plane had to wait for one more passenger. It was a chilly, cloudy Sunday in New York, the 9th of October 2016. That evening, Mr. Trump would debate his Democratic opponent, Hillary Clinton, in St. Louis.

Inside the custom-fitted Boeing 757-200, about 40 people were in their seats, including candidate Trump. They could not leave without one last person: Rudy Giuliani.

Why were they waiting for him?

That moment, as much as any, maps the ground between Mr. Trump and Mr. Giuliani.

They had known each other for nearly 40 years. Mr. Trump was the gaudy, gold-veneered developer who somehow navigated the shoals of organized crime, labor racketeering and official corruption in the New York real estate market of the 1980s, even as Mr. Giuliani was becoming so well known as a federal prosecutor that he kept a mental scorecard of his television appearances. (“Actually, it was only two nights,” Mr. Giuliani told a man in 1985 who mentioned he had just seen him five times on television. “Last week, it was five.”)

With Mr. Trump as co-chairman of his first campaign fund-raiser, Mr. Giuliani ran unsuccessfully for mayor in 1989. He won the next time, in 1993, and served until the end of 2001. For the world, he embodied resilience following Sept. 11, a stature he would parlay into wealth but not a successful presidential candidacy. After a dismal showing in the 2008 Republican primaries, in which he spent more than $60 million and won no delegates, he and Mrs. Giuliani retreated to her family’s home in Florida. There he fell into what she called a lingering “catatonic” state. He never fully returned to his law firm, Bracewell Giuliani — “his specialty was being Rudy,” his ex-partner, Mr. Oxford, said — but in time resumed giving paid speeches and running a lucrative security consultancy.

As the years of Barack Obama’s presidency passed, Mr. Giuliani’s voice seemed to carry farthest when it was keyed to harsh or apocalyptic tones. Faintly echoing Mr. Trump’s falsehood about the president’s origins, he questioned Mr. Obama’s Americanism (“He wasn’t brought up the way you were brought up, and I was brought up, through love of this country,” he said). Apart from such flare-ups, he largely dropped out of public conversation.

“Before the 2016 election, Rudy was running around hawking Life Lock on commercials that ran at 2 a.m. on channel 83,” a longtime close aide said.

Mr. Giuliani had not raced to sign on with Trump 2016, waiting until the nomination was nearly inevitable, but few bigger names beat him to it.

Prominent Republicans who now style themselves devoted allies of Mr. Trump spoke of him then with acid revulsion or clenched-teeth neutrality. The campaign needed someone able to dial into a steady state of rage on a moment’s notice, even a high-mileage ex-politician scarcely known to a younger generation of voters.

Given a speaking spot of honor at the Republican convention, Mr. Giuliani roared: “There’s — there’s — there’s no next election! This is it! There’s no more time for us left to revive our great country!”

During the last three months of the campaign, he spun like a tornado from one television studio to the next or jetted around the country, at every stop hurling charges of corruption like boiling brimstone at anyone standing in Mr. Trump’s way.

“He’d do an event with then-candidate Trump, and then he’d speak at a different event with Pence and then do one on his own,” David Bossie, the deputy campaign manager, said.

None of that compared to his work on the Sunday when the Trump campaign jet waited at La Guardia.

Two days earlier, an off-camera tape from the television show “Access Hollywood” had been released of Mr. Trump speaking in crude terms about how his celebrity status gave him license to sexually assault women.

Mr. Trump’s usual surrogates — Kellyanne Conway, Reince Priebus, Chris Christie — had been booked to appear on the Sunday shows before the tape came out. When it did, they all bailed.

Then Mr. Giuliani stepped forward.

“Rudy was the only person willing to go on television to defend Donald Trump,” Mr. Bossie said.

Mr. Giuliani spent that morning rushing between studios — he appeared on all five major networks — pausing long enough to strike a penitential chord and write off Mr. Trump’s words as unfortunate locker-room talk.

Considering the circumstances, the campaign staff believed Mr. Giuliani had blunted the political blow Mr. Trump had inflicted on Mr. Trump. “Most people thought he did a great job,” Mr. Bossie said.

When Mr. Giuliani boarded the plane, spent from his labors, he strode down the aisle a conquering hero, swapping high-fives. Then he settled across from Mr. Trump.

Everyone could hear what the candidate said next.

“Man, Rudy,” Mr. Trump said, “you sucked. You were weak. Low-energy.”

Mr. Giuliani slumped in his seat, one witness said. The plane grew silent.

By day’s end, Mr. Giuliani was back in front of the cameras, claiming victory for Mr. Trump in the debate. And his most important work for the campaign was yet to come.

On Oct. 25, 2016, exactly two weeks until Election Day, Mr. Giuliani appeared on “Fox and Friends,” and was asked what the Trump campaign would do with the remaining time.

“We’ve got a couple of surprises left,” Mr. Giuliani said, chuckling but coyly refusing to be drawn out on specifics.

“I think he’s got a surprise or two that you’re going to hear about in the next few days,” he told another interviewer. “I mean, I’m talking about some pretty big surprises.”

Unknown to the public, the F.B.I. had recently obtained a laptop used by one of Mrs. Clinton’s aides that had not been examined during the investigation of her private email server. That inquiry had concluded in July without charges, but the newly discovered laptop contained about 50,000 emails that might have been relevant. F.B.I. agents planned to go through them in due course, but several ranking officials did not see that any mad rush was called for, the Justice Department inspector general would later report. They believed — correctly, as it turned out — that the emails would be similar to the hundreds of thousands already examined.

Then Mr. Giuliani began dropping those broad hints of a “surprise,” adding that he knew F.B.I. agents were very upset. It seemed apparent to Attorney General Loretta Lynch that leaks were coming from the New York office of the F.B.I., according to the inspector general. Faced with the likelihood that word of the emails would be coming out one way or another, the F.B.I. director, James Comey, announced a review of the newly discovered cache. It played as a stunning piece of news, a fresh gust of scandal 11 days before the election.

Mr. Giuliani would later deny that he had heard about the emails from F.B.I. agents, though he had bragged about that in broadcast interviews.

Years before, he had shown that working with virtually nothing, he could cultivate the mere existence of investigations to his political benefit. Early in his first term as mayor, facing criticism over patronage hires, Mr. Giuliani and aides announced spectacular claims that a widely respected commissioner in the previous administration, Richard Murphy, had overspent his budget by millions of dollars for political reasons. Moreover, computer records seemed to have been destroyed in a suspicious burglary. The heat shifted from the reality of Mr. Giuliani’s patronage hires to the wispy vapors of the Murphy investigation. A year later, it emerged that Mr. Murphy had neither overspent nor done anything wrong, and that no records had been destroyed or stolen. Mayor Giuliani shrugged.

“This happens all the time,” he said. “And you write about those things all the time. Sometimes they turn out to be true. And sometimes they turn out to be wrong.”

So it was with the emails. With two days to go until the 2016 election, Mr. Comey said the review of the material in the laptop had not changed the bureau’s view that Mrs. Clinton had not committed a crime. The unquantifiable damage, though, had been done.

Declaring victory on election night, Mr. Trump hailed his family and his campaign staff.

One more person was singled out.

“I want to give a very special thanks to our former mayor, Rudy Giuliani,” Mr. Trump shouted, to chants of “Rudy, Rudy.” “That Rudy never changes. Where’s Rudy? Where is he?” A moment later, spotting him, Mr. Trump called again, “Oh, Rudy, get up here.”

With that, Mr. Giuliani stepped onto the stage, holding his wife’s hand, joining the Trump family.

The Inner Circle

Representing the president of the United States was, Mr. Giuliani said, “kind of a once-in-a-lifetime opportunity.”

He grabbed it. He strode across the public stage as a man without border or boundary, Full Throttle Giuliani — “I am a high-functioning human being, able to outwork people half my age,” he told New York magazine — blending the rare opportunity to serve the president with far more ordinary chances to profit from his closeness to power.

He became a one-stop human bazaar for the trade of money, favors and influence, certain that he was incorruptible.

“I’m probably the most ethical person you ever met,” he said.

There are conflicting accounts of why Mr. Giuliani did not get the State Department position he campaigned for in 2016, and of whether anyone other than himself even thought it was a real possibility, but his years of lucrative consulting payments from foreign governments since leaving City Hall would certainly have made for a complicated Senate confirmation.

So he returned in January 2017 to his partnership at Greenberg Traurig. He was also running a consulting company, Giuliani Security & Safety, with mostly foreign clients.

Yet for all that, he seemed to be itching to get back inside.

Out of the blue, he would call John Dowd, an old colleague from their days as young lawyers. Mr. Dowd had known Mr. Giuliani as a 30-year-old prosecutor whose withering cross-examination drove a sitting congressman to halt his own trial and plead guilty.

Now, though, Mr. Dowd was the president’s chief lawyer in the special counsel’s investigation of Russian interference in the 2016 election. Mr. Giuliani would phone just to volunteer suggestions or help, Mr. Dowd said.

“When I had the lead,” Mr. Dowd said, “he always had my back.”

In year one of the investigation, President Trump went through multiple lawyers, including Mr. Dowd. By spring 2018, Mr. Trump was having a hard time getting top legal talent to work on the case.

Up stepped Mr. Giuliani, who said he would serve without pay.

The Trump administration turned out to be very good for the business of being Rudy Giuliani, though it was no simple matter to say precisely what that was.

“Probably in the last two years, people have talked to me about hundreds of deals,” Mr. Giuliani said this fall.

As an insurgent, Mr. Trump arrived in Washington without the camp followers of brand-name lobbyists and insiders who set up shop with each new administration. Their absence heightened the value of the few people known to have influence with Mr. Trump, like Mr. Giuliani. Before and after he became the president’s personal lawyer, he thrived.

He hired himself out to a Turkish money launderer, Reza Zarrab, and argued his case directly to the president and the secretary of state, Rex Tillerson, in the Oval Office. Mr. Zarrab had been accused of moving $10 billion in gold and cash to Iran, evading American sanctions. He eventually pleaded guilty and became a prosecution witness.

That was not the only piece of Turkish business Mr. Giuliani brought before the president, or so aides to Mr. Trump suspected. They believed that on his regular visits to the White House, he was pushing the president to deport a Turkish Muslim cleric — a prize sought by Turkey’s president, Recep Tayyip Erdogan, who saw the man as an enemy of his regime. Mr. Giuliani called the claim that he was lobbying on that issue “stupid” and untrue. Still, for a short time, his access to the Oval Office was curbed.

He got paid to promote an ethane-methane deal in Uzbekistan. His security consultancy signed contracts with the government of Bahrain and a Ukrainian-Russian developer. Other work included engagements with governments, groups, individuals and causes in Romania, Iran, Brazil and Venezuela.

Trying to dazzle a woman on a date, he took her to a reception on the rooftop of the Hay Adams Hotel thrown by a lobbyist for the Democratic Republic of Congo. The Congolese, who were hoping to get America to back off sanctions, wanted his advice on how to please the Trump administration.

He seemed taken aback when reporters questioned him about his private business clients. “I’m not going to answer any more of your ####### questions because this is getting to be harassment,” he said in an interview last month.

One of those clients had cost him big dollars.

When he announced that he would be representing Mr. Trump, he said he would be taking a leave of absence from Greenberg Traurig. But his partners, and some of their clients, had had their fill of being associated with Mr. Trump. The firm said Mr. Giuliani was resigning. He said it was a mutual decision.

The loss of the $6 million income came with one consolation. No longer would Mr. Giuliani be subject to a moratorium on his TV appearances, imposed by the firm’s buttoned-down reticence. “The last year and a half, I haven’t been on television,” Mr. Giuliani said in May 2018. “Frankly, I’ve missed it.”

He returned to the airwaves with mesmerizing announcements and claims. Contradicting Mr. Trump, he said the president had indeed reimbursed one of his former lawyers, Michael Cohen, for the hush money paid to a pornographic film actress who said she had had a sexual encounter with Mr. Trump. A typical errand for a lawyer, he averred, though many begged to differ.

Mr. Giuliani denounced F.B.I. agents and federal prosecutors investigating the president and Mr. Cohen as thugs, storm troopers, bumbling. (Mr. Cohen, now in prison for his role in the hush-money scheme, said the investigators who raided his office had been polite; when he turned against Mr. Trump, he was declared a “scumbag” by Mr. Giuliani.)

Other lawyers on the Trump team were dismayed by his rhetoric, but Mr. Giuliani said it was tactical, regardless of how unhinged it seemed. Once he learned that the special counsel, Robert S. Mueller III, had decided that Justice Department policy forbade the criminal indictment of a sitting president, he said, he viewed impeachment as Mr. Trump’s only risk. That would be a public relations war, not a legal one, he explained, with the battles fought on television — an arena that Mr. Mueller did not contest. During his barrage, public opinion shifted slightly against an impeachment based on the Mueller findings, and Congress showed little appetite for pursuing it. Mr. Giuliani took victory laps.

With scant attention at first, he shifted the theater of combat away from television screens, and into murky Ukraine politics.

The Ukrainians

Without Mr. Giuliani’s push for money and frank yearning for relevance, the Trump Ukrainian initiative might never have amounted to much more than presidential tweetstorms. Mr. Giuliani compressed the digital gases of the president’s suspicions and wishful theories into what is now the molten core of impeachment.

Nothing shows how few limits Mr. Giuliani observed as plainly as his extended bear-hugs of Lev Parnas or Igor Fruman, his friends, clients and fellow emissaries for the president of the United States — the men he brought to his 9/11 dinner at the Maloney & Porcelli steakhouse in Manhattan.

In just about every snapshot from their travels, and there are many, Mr. Giuliani has a big grin on his face when he poses with Mr. Parnas and Mr. Fruman, two Florida men who were trying to hustle up business in Ukraine for an energy company they had just created.

They are simultaneously minor characters in the impeachment saga and very telling ones.

Mr. Giuliani may have been stopped from becoming secretary of state in 2017 by his business entanglements, but as Mr. Trump’s personal lawyer in 2019, he created and oversaw the dominant American foreign-policy channel with Ukraine, running the president’s affairs, his clients’ and his own through it.

That brought Mr. Parnas and Mr. Fruman into the president’s wake, sea gulls following an ocean liner.

When they met Mr. Giuliani last year, Mr. Parnas, born in Ukraine, and Mr. Fruman, a native of Belarus, were on the prowl for influence to help their companies, and over time would plow about $700,000 into political campaigns.

Mr. Fruman also had a business distributing luxury products in Ukraine, including yachts, jewelry, cars and electronics.

Mr. Parnas’s résumé includes work for companies that sold penny stocks in New York, a string of evictions and lawsuits in Florida and a judgment, now approaching $700,000, owed to an investor in a film project. He started a company called Fraud Guarantee, to provide due diligence services for investors. Like other business ventures of his, it was a bust. But it managed to pay $500,000 to Mr. Giuliani, who served as godfather for Mr. Parnas’s newborn son and attended the bris in Boca Raton, Fla.

The three men enjoyed private dinners in Washington, Florida, New York. Trips to Paris, Warsaw, Madrid. At a Yankee game in London, Mr. Giuliani, sporting one of the four diamond-encrusted World Series rings he’d gotten from the team, ushered them onto the field and into the dugout.

Mr. Giuliani opened doors for them, and they reciprocated at an opportune moment.

Late last year, Mr. Giuliani began to pursue information in Ukraine that he believed might show that the Mueller inquiry was built on a false premise, that it was really Ukrainians who meddled in the election and then framed the Russians for it.

This had long been the claim of Paul Manafort, the former Trump campaign chairman, now serving seven and a half years in federal prison for laundering millions of dollars from the Russia-aligned political party in Ukraine.

Mr. Manafort maintained that he and Mr. Trump were victims of Ukrainian meddling that took two forms: the release of a mysterious slush fund ledger that detailed payments by the Russia-aligned party, including $12.7 million earmarked for Mr. Manafort; and the hacking of Democratic National Committee computers that was blamed on Russia.

“The original investigation came to me from an investigator who had a client who said that the Ukrainians were the ones who did the hacking,” Mr. Giuliani said in April. In addition, he said, he was told that the release of the ledger was a malignant act by Ukrainian forces hostile to Mr. Trump — and that it might be a forgery.

So, he said, he had a duty to Mr. Trump to run it down.

“I think if I didn’t do it, I wouldn’t be a good lawyer,” Mr. Giuliani said.

Far more than a lawyer serving a client in a legal matter, though, Mr. Giuliani continued his Ukraine project long after Mr. Trump was clear of any jeopardy from the Mueller investigation, which ended in March.

Pinning the 2016 cyberattacks on Ukraine was a steep hill to climb, as the Senate Intelligence Committee had unequivocally found that they were a Russian operation. Even so, Mr. Giuliani demanded that the country’s new president announce an investigation of it, according to Gordon Sondland, the American ambassador to the European Union.

Equally difficult would be showing that Mr. Manafort was a victim of a forged paper ledger: Electronic bank records were so overwhelming that he pleaded guilty.

Nevertheless, if blame were seen to have shifted to Ukraine in these episodes, Mr. Giuliani would provide balm for Mr. Trump’s lingering furies that the findings of Russian involvement had tainted his presidency. Debunking the slush-fund ledger could also help build the case for a pardon of Mr. Manafort, Mr. Giuliani said.

Enter Mr. Parnas and Mr. Fruman, guides in Mr. Giuliani’s search for vindication of assorted conspiracy theories.

They connected Mr. Giuliani to a former prosecutor in Ukraine who added another twist to the plot. He claimed that Vice President Joseph R. Biden Jr. had forced his removal because Mr. Biden’s son, Hunter Biden, had been given a lucrative, little-show position by an oligarch who wanted the prosecutor out. Proving this would be yet another steep hill to climb, as the prosecutor’s record was so dismal that his dismissal was also sought by the European Union, the International Monetary Fund, the G7 and Ukrainians who protested his actions.

Still, Mr. Giuliani’s project expanded from Mr. Manafort to include the vilification of Mr. Biden and yet one more person: the American ambassador in Kyiv, Marie Yovanovitch.

The ambassador, an advocate for reforms in the Ukrainian energy sector, testified that she believed Mr. Parnas and Mr. Fruman saw her as an obstacle to their business plans. Mr. Parnas assured people — prophetically — that she would be removed in short order.

Mr. Giuliani fed claims about the ambassador and Mr. Biden to a writer at The Hill, bundled articles and memos into folders from Trump hotels and sent it all to Secretary of State Mike Pompeo in a big White House envelope. Though the charges against the ambassador were decried by the State Department as fabrications, they were amplified on Twitter by Donald Trump Jr. She was abruptly ordered home.

Phone records show that Mr. Giuliani was in frequent touch with the White House during this time, including with a regular caller identified only as “-1,” who Congressional investigators suspect may be the president.

Mr. Parnas and Mr. Fruman also dangled American favors in front of Petro O. Poroshenko, president of Ukraine at the time, and two exiled Ukrainian oligarchs facing legal problems in the United States. In exchange, the oligarchs and the president were asked for their help in implicating the Bidens in bribery, or Ukraine in 2016 meddling.

In August, Mr. Giuliani met in Madrid with an adviser to Volodymyr Zelensky, the new Ukrainian president, and also told Mr. Sondland, the ambassador, that he wanted the Ukrainians to announce investigations. As Mr. Giuliani knew from experience, such an announcement at the right moment can be as lethal as a poison arrow, needing only to break the skin to do its damage.

By fall, as a whistle-blower’s complaint brought the pressure campaign into the light, the foundations of Mr. Giuliani’s work were crumbling. An ally of Mr. Giuliani said he saw no evidence that Vice President Biden or his son had broken Ukrainian law.

Mr. Giuliani himself publicly conceded in a Sept. 29 interview with ABC’s George Stephanopoulos that there was no evidence that Ukraine had hacked the Democratic computers, and said that he had never actively investigated it.

A few days before, he had appeared on CNN.

“Did you ask the Ukraine to investigate Joe Biden?” asked Chris Cuomo, the host.

“No,” Mr. Giuliani replied. “I actually didn’t.”

He held that position for 27 seconds. Mr. Cuomo followed up, “So you did ask Ukraine to look into Joe Biden?”

“Of course I did,” Mr. Giuliani replied.

His project to deliver a crushing blow against a Trump opponent, and to establish that Mr. Trump — not the Democrats — had been the victim of foreign interference in the 2016 election, would fade into a toxic fog of impeachment charges.

At the same time, The New York Times reported that contrary to Mr. Giuliani’s claim that he had no business interests in Ukraine, he had negotiated with officials there for up to $500,000 in contracts that would involve the recovery of looted assets.

And during an August trip to Spain, Mr. Giuliani also did business unrelated to Ukraine: He met with a Venezuelan oligarch facing legal troubles from federal prosecutors in Florida, as The Washington Post reported. (One month later, as The Times reported, Mr. Giuliani held a high-level meeting on the man’s case with Justice Department officials in Washington.)

Mr. Giuliani and his two friends got together for lunch on Oct. 9, at the Trump International Hotel in Washington, the company cafeteria of Trump-world, where hamburgers go for $26 and the least expensive shots of Macallan are $29.

All three were heading to Vienna — Mr. Parnas and Mr. Fruman that very evening, Mr. Giuliani the next night. One of their sources, the unhappy ex-prosecutor, was going to be interviewed there by Sean Hannity, the Fox News personality.

They probably did not know that this would turn out to be their last get-together, at least for a while.

That evening, as they waited to board their Vienna flight, Mr. Parnas and Mr. Fruman were arrested on charges of making illegal campaign contributions — in part, prosecutors charge, to influence the removal of the ambassador.

Few people could have been more astonished at Mr. Parnas’s access to the halls of power and prestige than those who say they were bilked or stiffed by him. A lawyer, Robert J. Hantman, represents a creditor with a judgment against Mr. Parnas.

“It’s unbelievable that these people would be in the White House, or be hanging out with Giuliani,” Mr. Hantman said. “For Giuliani, the president, or anyone who wants to work with him to not have googled him, it’s unreal.”

In a world with few boundaries or limits, it was very real.

Full-Time Hero

Mr. Giuliani was far from a Lone Ranger in the Ukraine pressure campaign. Top figures in the administration knew of it or worked with him. “Everyone was in the loop,” Mr. Sondland testified.

But it was Mr. Giuliani who served as the wrangler of business hustlers, compromised ex-prosecutors, Ukrainian oligarchs and a host of bewildered American diplomats and Ukrainian elected officials who could not entirely fathom how he had come to wield such outsize influence, or to what ends he was wielding it.

And what of his relationship going forward with Mr. Trump, who effortlessly throws people under the bus? In October, the president praised Mr. Sondland on Twitter as a “really good man and great American.” When the ambassador testified last month that he had been acting on the president’s orders in pressuring Ukraine, Mr. Trump said: “I don’t know him very well. I have not spoken to him much.”

After signs of distance between the president and Mr. Giuliani — when the president hesitated about confirming that he was still his personal lawyer, Mr. Giuliani made a “joke” to The Guardian about having “very, very good insurance” — Mr. Trump gushed praise for him on Twitter and on “Fox and Friends.”

Mr. Giuliani said he appreciated the show of support, but added: “I’m not some little schmuck that needs Daddy to protect him.”

The Rudolph W. Giuliani business has been hurt, he said, because potential clients are afraid of being exposed to the endless scrutiny of his affairs.

His need for money shows no sign of ebbing. In addition to his domestic cash burdens, Mr. Giuliani is now said to be under investigation by federal prosecutors in the Southern District of New York. He has hired a team of lawyers to represent him. Legal fees could approach seven figures.

Reports indicate that the prosecutors are looking at his compliance with restrictions on lobbying. “I don’t do lobbying, ####### it,” Mr. Giuliani said, scoffing at the possibility of criminal charges. Although he negotiated with Ukrainian officials about representing them, and carried their messages to American officials and journalists, they ultimately did not come to any agreement, he said.

“I represented the president of the United States,” Mr. Giuliani said. “It is totally ridiculous to say that I was representing anyone else.”

Anthony Carbonetti, a City Hall aide to Mr. Giuliani and a longtime friend, said he worried that what he saw as Mr. Giuliani’s groundbreaking years as New York mayor would be forgotten behind the sky-filling spectacle of Mr. Trump.

“The fact that this is what he’ll be known for is painful,” Mr. Carbonetti said. “His public persona has been dominated by his representation of the president for the last two years, so that has become the public perception of him. I don’t think anyone goes back in time.”

Whatever his friends’ misgivings, Mr. Giuliani remains sure as ever that he is in the right.

His mission, he maintained, uncovered “one of our more major scandals.” Evidence against the Bidens is in his safe, he wrote on Twitter, adding, “If I disappear, it will appear immediately.”

Just last week, The Times reported, he returned to Ukraine to create television programs for a conservative network that he believes will show that he is right and House Democrats are wrong. Mr. Trump said on Saturday that Mr. Giuliani wanted to tell Congress what he had found.

So far, Mr. Giuliani has declined to testify, and described the impeachment hearings on Twitter as an “attempted coup takedown.”

The story, then, is being left to the people who survived being buried alive by Mr. Giuliani, including the cashiered Ambassador Yovanovitch.

“How is it that foreign corrupt interests could manipulate our government?” she asked in her testimony.

The face Mr. Giuliani sees in the mirror, he has always said, is of a man compelled by his idealism to purify government. “I get completely disgusted when I see public corruption,” he said.

Anyone who sees something else in him is mistaken, he said.

“I really try very hard to be super-ethical and always legal,” Mr. Giuliani said. “If it seems I’m not — it’s wrong, and I can explain it.”

As for how he will be viewed in the future, he has, at times, professed indifference. But in an interview with The Atlantic, Mr. Giuliani predicted that he would emerge from all the investigations wreathed in glory, an indispensable man who served the country against the odds.

“These morons,” Mr. Giuliani said. “When this is over, I will be the hero.”

The president’s personal attorney Rudolph W. Giuliani was on the phone in late 2018, pressing administration officials about his latest agenda item.

President Trump had nominated a career Foreign Service officer to become the U.S. ambassador to Qatar, a key post in a Middle Eastern country with tricky regional relationships, an important U.S. military installation and vast oil reserves.

Giuliani, who has said he had held a cybersecurity contract with Qatar in 2017 and early 2018, proposed replacing her with someone he said would be a better fit — Scott W. Taylor, a Trump-supporting former congressman from Virginia defeated in his reelection bid in November 2018, according to people familiar with his outreach.

Giuliani’s previously unreported attempts to shape the pick for the U.S. envoy to Qatar are part of an un­or­tho­dox foreign policy portfolio he has carved out for himself while also working as a power-broker-for-hire with direct access to the president and top administration officials.

The dual roles he has embraced are part of what longtime colleagues say has been a transformation of the once-iconic New York mayor into a multimillionaire consultant to powerful figures overseas.

In the three years since Trump took office, Giuliani has expanded his lucrative foreign consulting and legal practice, taking on clients that span the globe, from Turkey to Venezuela to Romania to Ukraine.

Along the way, he also has used his singular perch to try to influence U.S. policy and criminal investigations — at times pushing the interests of foreign figures who could benefit him financially.

In 2017, Giuliani tried to get Trump and top Cabinet members to make moves sought by Turkey while working as a lawyer for a gold trader from that country with ties to top government officials. This spring, he successfully helped oust U.S. ambassador to Ukraine Marie Yovanovitch, a top target of a Ukrainian prosecutor whom he considered representing in a six-figure contract. In September, he urged Justice Department officials not to pursue a case against a wealthy Venezuelan energy executive who had hired him as a private attorney.

Giuliani has said he separates his private business from the work he does for the president for free. He has said the kinds of services he provides his foreign clients do not require registering with the U.S. government as a foreign lobbyist.

But since the start of the administration, his actions have caused persistent alarm among Trump’s advisers, who worry that it is often not clear who Giuliani is representing — the president, his private clients or his own foreign policy views — in his meetings at the White House and in foreign cities, according to people familiar with the concerns who spoke on the condition of anonymity to describe internal discussions.

Those worries have become acute since Giuliani emerged as a central figure in the Ukraine pressure campaign that is the subject of the House impeachment inquiry — and the arrests of two of his associates, Lev Parnas and Igor Fruman, who assisted him in that effort.

Federal prosecutors in New York are scrutinizing Giuliani’s business ties to the men and his consulting business as part of a broad probe, according to people familiar with the investigation.

In several conversations in recent months, Attorney General William P. Barr has counseled Trump in general terms that Giuliani has become a liability and a problem for the administration, according to multiple people familiar with the conversations. In one discussion, the attorney general warned the president that he was not being well-served by his lawyer, one person with knowledge of the episode said.

The Justice Department and the White House declined to comment. Giuliani did not respond to multiple calls and messages seeking his comment. His lawyer declined to comment.

Giuliani has assured the president that he is not in legal trouble, according to White House aides. And Trump has so far resisted entreaties to distance himself from the former New York mayor, telling others that he appreciates Giuliani’s combative media appearances on his behalf, according to White House officials and Trump advisers.

 “He’s a good man and he’s an honorable guy and he’s a great crime fighter, corruption fighter,” the president said in an interview with Bill O’Reilly last month.

Last week, even as the House began drafting articles of impeachment, Giuliani kept up his work abroad on the president’s behalf, swooping into Kyiv to meet with Ukrainian prosecutors who he claims have damaging information about Democrats.

But the federal probe — being run out of the U.S. attorney’s office in Manhattan that Giuliani once led — appears to be delving into his foreign entanglements.

In recent weeks, prosecutors subpoenaed a consulting firm founded by former FBI director Louis J. Freeh, which hired Giuliani to write an August 2018 letter to Romanian officials calling for an amnesty for people prosecuted for corruption, a policy change that would have benefited a Freeh client, according to people familiar with the move. The subpoena has not been previously reported.

Freeh’s firm declined to comment, as did a spokesman for the U.S. attorney’s office in Manhattan.

This examination of Giuliani’s activities is based on interviews with more than 25 of his associates, current and former administration officials and other people familiar with his work, many of whom spoke on the condition of anonymity because of the ongoing criminal investigation.

In recent interviews, Giuliani told The Washington Post that questions about his foreign clients are “diversions by Democrats hoping to shoot the messenger” and an effort to distract from information he is uncovering about the president’s political opponents, such as former vice president Joe Biden.

“The Swamp Media is going back 20 years to find anything I could have done which they can paint as ‘wrong,’ ” he wrote in a tweet this fall.

Embracing a new lifestyle

Giuliani first came to prominence as the mob-fighting U.S. attorney in Manhattan in the 1980s, a position that helped propel him into the New York mayor’s office in 1994. His calm, take-charge leadership during the Sept. 11, 2001, terrorist attacks brought him international acclaim.

After leaving office, he parlayed that fame into a new role as a paid speaker around the world. The money that suddenly began flowing his way was a revelation, according to people who knew him.

One longtime friend recalled that during his travels for speeches abroad, Giuliani learned he could get paid $1 million or more as a consultant to foreign interests. He was stunned — and enticed, said the friend, who spoke on the condition of anonymity to describe private conversations.

Soon, Giuliani began living a much more affluent lifestyle, enjoying a house in the Hamptons, premium cigars, fine scotch, first-class travel and a luxury residence in New York. In 2003, he married his third wife, Judith Nathan, in an elaborate ceremony on the lawn of Gracie Mansion attended by 400 guests, including Trump. (The two are now in the midst of a bitter divorce.)

By the time Giuliani ran for president in 2008 — a bid that started strong but fizzled — his financial disclosure statement showed he had made $9.2 million for speeches alone between 2006 and mid-2007, many from domestic companies but also from foreign sponsors and think tanks. He made additional millions through his consulting company and his law firm, Bracewell & Giuliani, the disclosure showed.

But Giuliani’s failed presidential bid left the onetime hero “cast off into the political wilderness again,” said Andrew Kirtzman, a journalist who covered his political rise and wrote a 2001 biography of the former mayor.

He redoubled his efforts to make money, friends and associates noted.

“His values seemed to change,” Kirtzman said. “He was the least materialistic figure I’d ever covered back in his prosecutorial and mayoral days. His interest was always in power, not money. Then he became a man who was very interested in money.”

In the process, the former prosecutor began to drift away from colleagues he had known for decades, some of whom now express bewilderment at his transformation.

“There was a time when he wouldn’t take dirty money or questionable money or money of dubious origin,” said Ken Frydman, who served as the press secretary for Giuliani’s 1993 mayoral campaign, noting Giuliani was known then for vetting donors especially aggressively. “Today, it seems he’ll take money from anyone.”

Like Trump, Giuliani has always had a stubborn refusal to admit mistakes, Frydman said.

“Don’t back down. Don’t apologize,” Frydman said of Giuliani’s philosophy. But he said there is an “an intensity” to Giuliani now that goes beyond what he remembers: “He’s turned on the afterburners. He’s Rudy on steroids.”

Giuliani was soon moving in the same social circles as Trump, whom he had known for years in New York, emerging as one of the developer’s most vocal surrogates in the 2016 campaign.

After Trump’s surprise victory, Giuliani made clear he wanted to be named secretary of state, according to current and former administration officials. But a team of lawyers vetting potential administration appointees raised red flags about possible conflicts of interest arising from his work overseas, according to the officials.

A few weeks after Trump’s election, Giuliani announced that he had taken himself out of the running for the job. On Fox News, he said he planned to pursue his private legal and consulting business “with even more enthusiasm” than before Trump’s election.

Expanding foreign practice

The former New York mayor had robust work overseas before Trump took office. His companies, Giuliani Partners and Giuliani Security & Safety, provided security and emergency management consulting to governments in Peru, Chile, Argentina and Ukraine, among others. He gave paid speeches around the world, including to Mujahideen-e-Khalq, or MEK, an Iranian resistance group operating in exile that was listed as a terrorist group by the State Department as recently as 2012.

But Trump’s election provided Giuliani with a substantially bigger platform — and newfound access to the top levels of U.S. decision-making.

He became a mainstay at the Trump International Hotel down the street from the White House, where he has spent long evenings meeting friends and potential business partners. When he needs to privately discuss deals, he convenes meetings at some of his favorite cigar bars, including Shelly’s Back Room in Washington and New York’s Grand Havana Room, according to people familiar with the sessions.

‘Had I not been there, I wouldn’t have met Rudy’: The tale of the Arabian princess and the Trump International Hotel

Giuliani has bragged to other Trump allies that he has made millions of dollars since the president took office, according to people familiar with his comments.

He also has regularly boasted about his access to Trump and the closeness of their friendship, said a senior U.S. official who interacted with Giuliani.

In one meeting with a prominent Ukrainian political figure in early 2018, Giuliani was explicit that hiring him would provide a route to the president, according to a person in attendance.

“It was just so clear what he was peddling. He was pushing for business, and his pitch was, ‘I’m close to the White House, I’m close to Trump. If you want to get in there, I’m your guy,’ ” the person said. In that case, the Ukrainian did not hire Giuliani.

Giuliani used his access to Trump in 2017 to push for two controversial actions sought by Turkish President Recep Tayyip Erdogan, as The Post has previously reported.

Early that year, he was hired by the legal team of a Turkish-Iranian gold trader, Reza Zarrab, who was charged in New York with violating U.S. sanctions against Iran. The matter was of keen interest to Erdogan, who said Zarrab was a political “hostage” of American law enforcement. Giuliani met with the Turkish president on a visit to Istanbul in February 2017 to discuss a possible “state-to-state resolution in this case,” according to court filings in the Zarrab case.

In the fall of 2017, Giuliani attended an Oval Office meeting where Trump urged then-Secretary of State Rex Tillerson to consult with Giuliani and craft a diplomatic deal that would involve dropping charges against Giuliani’s client in exchange for concessions from Turkey, such as the release of an American pastor in Turkish custody.

People familiar with the incident have said Tillerson was shocked at what he viewed as an inappropriate request to intervene in a criminal matter. Tillerson has declined to comment.

Giuliani told The Post he sought a prisoner exchange but declined to comment on any private discussions on the topic. He said he did not need to register as a foreign agent for his Turkish advocacy because his only goal was to assist the legal case of his client, Zarrab. Defense attorneys are not required to register as foreign lobbyists when they assist clients in criminal or civil matters.

In late 2017, Zarrab pleaded guilty to orchestrating a multibillion-dollar conspiracy to evade U.S. sanctions against Iran by disguising money transfers so they would appear to be legitimate gold trades. He testified in federal court that the scheme was approved by Erdogan. Turkish officials denied any wrongdoing.

Trump asked Tillerson to help broker deal to end U.S. prosecution of Turkish trader represented by Giuliani

That year, Giuliani also persistently pushed Trump on another top concern of the Turkish president: extraditing exiled Turkish cleric Fethullah Gulen back to his home country to face prosecution. State Department and National Security Council officials have argued against such a move, but Trump appeared receptive to the idea, pressing his advisers about Gulen’s status, as The Post previously reported.

Giuliani declined at the time to discuss whether he advocated for Gulen’s extradition, writing in a text message earlier this year: “can’t comment on it that would be complete attorney client privilege but sounds wacky.” He later denied that he tried to intervene in the case.

“I don’t represent foreign government in front of the U.S. government,” he told The Post earlier this year. “I’ve never registered to lobby.”

But inside the White House, officials were so disturbed by how he was promoting Turkey’s causes with Trump that then-Chief of Staff Reince Priebus pulled Giuliani aside in the West Wing in 2017 and warned him against lobbying for the country, officials said.

New proximity to president

In April 2018, Giuliani formally joined Trump’s legal team to help him deal with special counsel Robert S. Mueller III’s investigation, a position that required him to talk frequently with the president.

White House aides fear Giuliani has used his role as the president’s lawyer to promote the interests of private clients, fretting that they do not know who he represents, officials said. His conversations with Trump are protected by attorney-client privilege, meaning even Trump’s closest aides are not briefed on what they discuss.

Priebus’s successor, John F. Kelly, tried to limit Giuliani’s reach, scheduling his meetings with Trump at the White House residence, so he would not interact with other White House staff, former administration officials said. Kelly also told others he did not want to be part of calls or meetings with Giuliani, the people said.

Giuliani has insisted that he keeps his role as the president’s lawyer separate from the work he does for foreign interests.

“I’ve never lobbied him on anything,” Giuliani told The Post earlier this year, referring to Trump.

But he has continued to take on foreign clients, and, behind the scenes, his advocacy on foreign policy issues has not ceased, according to people familiar with his activities.

In the months after Giuliani joined Trump’s legal team, he began discussions with a group interested in influencing U.S. policy in Venezuela.

In the summer of 2018, over cigars and whiskey at New York’s Grand Havana Room, Giuliani met with Parnas and two American business executives with investments in the country seeking his advice on how to open a back channel of communication between Trump and Venezuela’s socialist leader, Nicolás Maduro, according to people familiar with the gathering.

As part of the previously unreported talks, Giuliani agreed to help find a way to negotiate with Maduro and reach a diplomatic solution to the political chaos and economic collapse overtaking the country, they said.

Weeks later, he told the group that he had met with John Bolton, the president’s national security adviser, to discuss the idea.

Charles Cooper, an attorney for Bolton, declined to comment.

Bolton’s distaste for Giuliani’s foreign policy freelancing has emerged during the impeachment inquiry. Former national security official Fiona Hill testified that Bolton warned her not to interact with the president’s lawyer, calling him “a hand grenade that is going to blow everybody up.”

After a contested Venezuelan election in January, Bolton urged Trump to formally recognize legislative leader Juan Guaidó as the country’s leader instead. Maduro has refused to step down and the United States imposed stiffer sanctions in response.

By this summer, Giuliani had picked up an important Venezuelan client: energy executive Alejandro Betancourt López, who hired Giuliani to help him contend with a Justice Department investigation of alleged money laundering and bribery, according to people familiar with the situation.

Giuliani stayed at Betancourt’s historic estate outside Madrid in August, when he met with a top aide to Ukrainian President Volodymyr Zelensky and urged him to open investigations into the 2016 election and Biden’s son Hunter’s work for a Ukrainian gas company, as The Post previously reported.

A wealthy Venezuelan hosted Giuliani as he pursued Ukraine campaign. Then Giuliani lobbied the Justice Department on his behalf

On Aug. 13, days after returning from Madrid, Giuliani was back at the Grand Havana Room, meeting with another potential client: the National Bank of Ukraine, which had taken over a bank once owned by Ukrainian businessman Ihor Kolomoisky, according to a person familiar with the meeting.

He suggested that lawyers with the law firm Quinn Emanuel, which represents the Ukrainian state-owned bank, hire him to wage a public campaign against Kolomoisky, with whom the bank is engaged in a complicated legal battle. Kolomoisky is also considered a political supporter of Zelensky.

Giuliani told Bloomberg, which first reported the meeting, that he was approached by the lawyers for the bank to see whether he could help them with a civil suit. He said the timing was not right.

“Since representing Trump I have considered and turned down all deals in Ukraine, even those not presenting a conflict,” Giuliani tweeted last week.

A spokesman for Quinn Emanuel declined to comment.

Giuliani works for foreign clients while serving as Trump’s attorney

Interest in Qatar

Giuliani’s interest in U.S. foreign policy has often tracked with countries where he has had a financial interest.

That was the case with his efforts to shape the pick for ambassador to Qatar, where he did security consulting work in 2017 and 2018 related to a hacking incident, Giuliani told The Post earlier this year.

He declined to describe the specific work he did but said his contract concluded before he was named Trump’s attorney in April 2018. He said that he did not register as a foreign lobbyist because he never lobbied U.S. officials on behalf of Qatar.

The Qatari Embassy in Washington declined to comment.

In November 2018, Trump nominated Mary Catherine Phee to fill the post of ambassador to Qatar, a key diplomatic job that had been vacant since June 2017. Phee had served as a career diplomat since 1991, including a stint as ambassador to South Sudan.

She is known as “an old school, talented diplomat” whose “strong point is the nitty-gritty of bilateral relations,” according to a former senior administration official involved in Middle East policy.

Scott Taylor, who wrote a 2015 book called “Trust Betrayed: Barack Obama, Hillary Clinton, and the Selling Out of America’s National Security,” had experience in the region and with energy policy. He served as a security contractor for Hunt Oil in Yemen from 2008 to 2010, Taylor told the Virginian-Pilot before his 2016 election. While in Congress, Taylor worked to build ties with Qatar, visiting the country in 2017 and speaking at a Qatari event in Washington in 2018.

Giuliani offered to promote Taylor as candidate for the post and help guide him through the process, according to a person familiar with his outreach.

During a night at a cigar bar in Friendship Heights in December and a lunch meeting the following day at the Trump hotel, Giuliani described a plan to promote Taylor for the job, the person said.

During the conversations, Giuliani told Taylor that he had done work in Qatar, but it was unclear why he was interested in shaping the ambassador pick.

In subsequent calls to administration officials, Giuliani argued that Taylor would be a better choice than Phee because he would be more supportive of Trump’s agenda, according to multiple people familiar with the conversations.

As the process moved along, Giuliani also told Taylor he had discussed the idea with the president, who had seemed enthusiastic, one person said.

When asked about his advocacy for Taylor in a November interview, Giuliani laughed and ended the call.

Reached by phone, Taylor — who this summer launched a campaign to unseat Sen. Mark R. Warner (D) — declined to comment on Giuliani’s effort to get him the appointment, saying only, “I had a lot of advocates on that.”

The State Department declined to comment.

Phee’s nomination expired when Congress adjourned last year and Trump has not renominated her. He also did not name Taylor, leaving the key job vacant.

Foreign work under scrutiny

The scope of the ongoing investigation by federal prosecutors in Manhattan is unclear, but the recent subpoena to Freeh’s firm indicates that investigators appear to be drilling into Giuliani’s work abroad.

In August 2018, Giuliani sent a letter to the Romanian president, expressing his concern that “excesses” by the nation’s anti-corruption agency were resulting in the prosecution of innocent people. Giuliani called for an amnesty for people convicted under the system.

Giuliani told The Post at the time that he was hired to send the letter by Freeh’s firm. He declined to say on whose behalf Freeh’s firm was working or how much he was paid.

But Freeh has said he was hired in July 2016 to conduct a review of the conviction of Gabriel “Puiu” Popoviciu, a Romanian real estate executive sentenced to seven years in prison for fraud.

Popoviciu originally hired Freeh at the recommendation of Hunter Biden, who had been retained by the Romanian, an attorney for the former vice president’s son, George R. Mesires, confirmed. The New York Times first reported Hunter Biden’s role. A Biden campaign official said Hunter Biden never discussed his Romania work with his father, who actively supported anti-corruption initiatives in the country.

Giuliani’s letter to the Romanian president, written on the letterhead of his firm Giuliani Partners, did not mention his relationship to Trump. But it caused an immediate stir in Bucharest, where news organizations highlighted Giuliani’s role as the president’s attorney and questioned whether the letter indicated a shift in U.S. support for the anti-corruption agency.

The State Department tried to distance itself from him. “Rudy Giuliani does not speak for the U.S. government on foreign policy,” an official told The Post at the time.

Giuliani letter criticizing Romania’s anti-corruption drive draws State Department attention

Giuliani has repeatedly dismissed questions about the propriety of his foreign work.

“5 different organizations are looking at 8 different cases trying to find something wrong. why if I’m not part of a Left Wung [sic] Witchunt for nailing Biden,” he wrote in a recent text message.

But people familiar with the current investigation have said federal prosecutors are exploring a wide range of potential crimes — including wire fraud and failure to register as a foreign agent — as they examine Giuliani’s relationship with his two associates, Parnas and Fruman.

The two men were charged in October with campaign finance violations. The allegations do not implicate Giuliani, and both have pleaded not guilty.

Parnas and Fruman were key intermediaries who helped connect Giuliani early this year with Ukrainian officials such as Ukraine’s then-top prosecutor, Yuri Lutsenko, who was offering damaging information about Trump’s political opponents, Giuliani and Parnas have said.

Giuliani’s efforts in Ukraine soon merged with official U.S. policy. He pushed White House and State Department officials to issue a visa to a former Ukrainian prosecutor who was blocked from traveling to the United States because of corruption allegations, according to testimony from U.S. officials during the impeachment hearings.

And he lobbied Secretary of State Mike Pompeo to dismiss the U.S. ambassador, speaking with Pompeo twice by phone and then sending him a packet of material advocating her removal, documents show.

Yovanovitch was removed from her post in May, the same month Trump directed top U.S. officials working on Ukraine policy to coordinate with his private attorney. By July, Trump was personally involved in the effort, pressing Zelensky by phone to work with Giuliani to open the investigations.

Giuliani has insisted he was not paid for the work he did for Trump. But he has acknowledged that in January he considered representing Lutsenko and the Ukrainian Ministry of Justice, writing a draft contract to formalize the deal in which he would have been paid $500,000.

He told the Wall Street Journal that he quickly decided against the arrangement, fearing it could pose a conflict with his representation of the president.

Last week, Giuliani traveled to Budapest, where he met with Lutsenko, then traveled to Kyiv, where he met with two members of Ukraine’s parliament who have called for a joint U.S.-Ukrainian parliamentary investigation into the gas company that hired Hunter Biden.

During the trip, Giuliani indicated he was speaking for the United States, writing on Twitter that until Ukraine investigates the “criminal conduct” of Biden, it “will be a major obstacle to the U.S. assisting Ukraine with its anti-corruption efforts.”

The president appeared pleased with his efforts, telling reporters Saturday that Giuliani was going to “make a report” to the attorney general and Congress.

“He says he has a lot of good information,” Trump said, adding: “I hear he has found plenty.”

Mick Mulvaney, the acting White House chief of staff, played a key role in carrying out President Trump’s demands to halt military aid to Ukraine.Credit...Doug Mills/The New York Times

WASHINGTON — Deep into a long flight to Japan aboard Air Force One with President Trump, Mick Mulvaney, the acting White House chief of staff, dashed off an email to an aide back in Washington.

“I’m just trying to tie up some loose ends,” Mr. Mulvaney wrote. “Did we ever find out about the money for Ukraine and whether we can hold it back?”

It was June 27, more than a week after Mr. Trump had first asked about putting a hold on security aid to Ukraine, an embattled American ally, and Mr. Mulvaney needed an answer.

The aide, Robert B. Blair, replied that it would be possible, but not pretty. “Expect Congress to become unhinged” if the White House tried to countermand spending passed by the House and Senate, he wrote in a previously undisclosed email. And, he wrote, it might further fuel the narrative that Mr. Trump was pro-Russia.

Mr. Blair was right, even if his prediction of a messy outcome was wildly understated. Mr. Trump’s order to hold $391 million worth of sniper rifles, rocket-propelled grenades, night vision goggles, medical aid and other equipment the Ukrainian military needed to fight a grinding war against Russian-backed separatists would help pave a path to the president’s impeachment.

The Democratic-led inquiry into Mr. Trump’s dealings with Ukraine this spring and summer established that the president was actively involved in parallel efforts — both secretive and highly unusual — to bring pressure on a country he viewed with suspicion, if not disdain.

One campaign, spearheaded by Rudolph W. Giuliani, the president’s personal lawyer, aimed to force Ukraine to conduct investigations that could help Mr. Trump politically, including one focused on a potential Democratic 2020 rival, former Vice President Joseph R. Biden Jr.

The other, which unfolded nearly simultaneously but has gotten less attention, was the president’s demand to withhold the security assistance. By late summer, the two efforts merged as American diplomats used the withheld aid as leverage in the effort to win a public commitment from the new Ukrainian president, Volodymyr Zelensky, to carry out the investigations Mr. Trump sought into Mr. Biden and unfounded or overblown theories about Ukraine interfering in the 2016 election.

Interviews with dozens of current and former administration officials, congressional aides and others, previously undisclosed emails and documents, and a close reading of thousands of pages of impeachment testimony provide the most complete account yet of the 84 days from when Mr. Trump first inquired about the money to his decision in September to relent.

What emerges is the story of how Mr. Trump’s demands sent shock waves through the White House and the Pentagon, created deep rifts within the senior ranks of his administration, left key aides like Mr. Mulvaney under intensifying scrutiny — and ended only after Mr. Trump learned of a damning whistle-blower report and came under pressure from influential Republican lawmakers.

In many ways, the havoc Mr. Giuliani and other Trump loyalists set off in the State Department by pursuing the investigations was matched by conflicts and confusion in the White House and Pentagon stemming from Mr. Trump’s order to withhold the aid.

Opposition to the order from his top national security advisers was more intense than previously known. In late August, Defense Secretary Mark T. Esper joined Secretary of State Mike Pompeo and John R. Bolton, the national security adviser at the time, for a previously undisclosed Oval Office meeting with the president where they tried but failed to convince him that releasing the aid was in interests of the United States.

By late summer, top lawyers at the Office of Management and Budget who had spoken to lawyers at the White House and the Justice Department in the weeks beforehand, were developing an argument — not previously divulged publicly — that Mr. Trump’s role as commander in chief would simply allow him to override Congress on the issue.

And Mr. Mulvaney is shown to have been deeply involved as a key conduit for transmitting Mr. Trump’s demands for the freeze across the administration.

The interviews and documents show how Mr. Trump used the bureaucracy to advance his agenda in the face of questions about its propriety and even legality from officials in the White House budget office and the Pentagon, many of whom say they were kept in the dark about the president’s motivations and had grown used to convention-flouting requests from the West Wing. One veteran budget official who raised questions about the legal justification was pushed aside.

Those carrying out Mr. Trump’s orders on the aid were for the most part operating in different lanes from those seeking the investigations, including Mr. Giuliani and a number of senior diplomats, including Gordon D. Sondland, the ambassador to the European Union, and Kurt D. Volker, the State Department’s special envoy for Ukraine and Russia.

The New York Times found that some key players are now offering a defense that they did not know the diplomatic push for the investigations was playing out at the same time they were implementing the aid freeze — or if they were aware of both channels, they did not connect the two.

Mr. Mulvaney is said by associates to have stepped out of the room whenever Mr. Trump would talk with Mr. Giuliani to preserve Mr. Trump’s attorney-client privilege, leaving him with limited knowledge about their efforts regarding Ukraine. Mr. Mulvaney has told associates he learned of the substance of Mr. Trump’s July 25 call weeks after the fact.

Yet testimony before the House suggests a different picture. Fiona Hill, a top deputy to Mr. Bolton at the time, told the impeachment inquiry about a July 10 White House meeting at which Mr. Sondland said Mr. Mulvaney had guaranteed that Mr. Zelensky would be invited to the White House if the Ukrainians agreed to the investigations — an arrangement that Mr. Bolton described as a “drug deal,” according to Ms. Hill.

Along with Mr. Bolton and others, Mr. Mulvaney and Mr. Blair have declined to cooperate with impeachment investigators and provide information to Congress under oath, an intensifying point of friction between the two parties as the Senate prepares for Mr. Trump’s impeachment trial.

At the center of the maelstrom was the Office of Management and Budget, a seldom-scrutinized arm of the White House that during the Trump administration has often had to find creative legal reasoning to justify the president’s unorthodox policy proposals, like his demand to divert Pentagon funding to his proposed wall along the border with Mexico.

In the Ukraine case, however, shock about the president’s decision spread across America’s national security apparatus — from the National Security Council to the State Department and the Pentagon. By September, after the freeze had become public and scrutiny was increasing, the blame game inside the administration was in full swing.

On Sept. 10, the day before Mr. Trump changed his mind, a political appointee at the budget office, Michael P. Duffey, wrote a lengthy email to the Pentagon’s top budget official, with whom he had been at odds throughout the summer about how long the agency could withhold the aid.

He asserted that the Defense Department had the authority to do more to ensure that the aid could be released to Ukraine by the congressionally mandated deadline of the end of that month, suggesting that responsibility for any failure should not rest with the White House.

Forty-three minutes later, the Pentagon official, Elaine McCusker, hit send on a brief but stinging reply.

“You can’t be serious,” she wrote. “I am speechless.”

‘We Need to Hold It Up’

For top officials inside the budget office, the first warning came on June 19.

Informed that the president had a problem with the aid, Mr. Blair called Russell T. Vought, the acting head of the Office of Management and Budget. “We need to hold it up,” he said, according to officials briefed about the conversation.

Typical of the Trump White House, the inquiry was not born of a rigorous policy process. Aides speculated that someone had shown Mr. Trump a news article about the Ukraine assistance and he demanded to know more.

Mr. Vought and his team took to Google, and came upon a piece in the conservative Washington Examiner saying that the Pentagon would pay for weapons and other military equipment for Ukraine, bringing American security aid to the country to $1.5 billion since 2014.

The money, the article noted, was coming at a critical moment: Mr. Zelensky, a onetime comedian, had called ending the armed conflict with Russia in eastern Ukraine his top priority — a move that would likely only happen if he could negotiate from a position of strength.

The budget office officials had little idea of why Mr. Trump was interested in the topic, but many of the president’s more senior aides were well aware of his feelings about Ukraine. Weeks earlier, in an Oval Office meeting on May 23, with Mr. Sondland, Mr. Mulvaney and Mr. Blair in attendance, Mr. Trump batted away assurances that Mr. Zelensky was committed to confronting corruption.

“They are all corrupt, they are all terrible people,” Mr. Trump said, according to testimony in the impeachment inquiry.

The United States had been planning to provide $391 million in military assistance to Ukraine in two chunks: $250 million allocated by the Pentagon for war-fighting equipment — from sniper rifles to rocket-propelled grenade launchers — and $141 million controlled by the State Department to buy night-vision devices, radar systems and yet more rocket-grenade launchers.

With the money having been appropriated by Congress, it would be hard for the administration to keep it from being spent by the end of the fiscal year on Sept. 30.

The task of dealing with the president’s demands fell primarily to a group of political appointees in the West Wing and the budget office, most with personal and professional ties to Mr. Mulvaney. There was no public announcement that Mr. Trump wanted the assistance withheld. Neither Congress nor the Ukrainian government was formally notified.

Mr. Mulvaney had first served in the administration as the budget director, after three terms in the House, where he earned a reputation as a firebrand conservative.

The four top political appointees helping Mr. Mulvaney execute the hold — Mr. Vought, Mr. Blair, Mr. Duffey and Mark Paoletta, the budget office’s top lawyer — all had extensive experience in either congressional budget politics or Republican and conservative causes.

Their efforts would cause tension and at times conflict between officials at the budget office and the Pentagon, some of whom watched with growing alarm.

A Question of Legality

The single largest chunk of the federal government’s annual discretionary budget, some $800 billion a year, goes to the Pentagon, spy agencies and the Department of Veterans Affairs. The career official in charge of managing the flow of all that money for the budget office is an Afghanistan war veteran named Mark Sandy.

After learning about the president’s June 19 request, Mr. Sandy contacted the Pentagon to learn more about the aid package. He also repeatedly pressed Mr. Duffey about why Mr. Trump had imposed the hold in the first place.

 “He didn’t provide an explicit response on the reason,” Mr. Sandy testified in the impeachment inquiry. “He simply said we need to let the hold take place — and I’m paraphrasing here — and then revisit this issue with the president.”

From the start, budget office officials took the position that the money did not have to go out the door until the end of September, giving them time to address the president’s questions.

It was easy enough for the White House to hold up the State Department portion of the funding. Since the State Department had not yet notified Congress of its plans to release the money, all it took was making sure that the notification did not happen.

Freezing the Pentagon’s $250 million portion was more difficult, since the Pentagon had already certified that Ukraine had met requirements set by Congress to show that it was addressing its endemic corruption and notified lawmakers of its intent to spend the money.

So on July 19, Mr. Duffey proposed an unusual solution: Mr. Sandy should attach a footnote to a routine budget document saying the money was being temporarily withheld.

Approving such requests is routine; Mr. Sandy processed hundreds each year. But attaching a footnote to block spending that the administration had already notified Congress was ready to go was not. Mr. Sandy said in testimony that he had never done it before in his 12 years at the agency.

And there was a problem with this maneuver: Mr. Sandy was concerned it might violate a law called the Impoundment Control Act that protects Congress’s spending power and prohibits the administration from blocking disbursement of the aid unless it notifies Congress.

“I asked about the duration of the hold and was told there was not clear guidance on that,” Mr. Sandy testified. “So that is what prompted my concern.”

Mr. Sandy sought advice from the top lawyers at the budget office.

A Pivotal Day

For a full month, the fact that Mr. Trump wanted to halt the aid remained confined primarily to a small group of officials.

That ended on July 18, when a group of top administration officials meeting on Ukraine policy — including some calling in from Kyiv — learned from a midlevel budget office official that the president had ordered the aid frozen.

“I and the others on the call sat in astonishment,” William B. Taylor Jr., the top United States diplomat in Ukraine, testified to House investigators. “In an instant, I realized that one of the key pillars of our strong support for Ukraine was threatened.”

That same day, aides on the House Foreign Affairs Committee received four calls from administration sources warning them about the hold and urging them to look into it.

A week later came Mr. Trump’s fateful July 25 call with Mr. Zelensky. Mr. Bolton, the national security adviser, had recommended the call take place in an effort to end the “incessant lobbying” from officials like Mr. Sondland that the two leaders connect.

Some of Mr. Trump’s aides had thought the call might lead Mr. Trump to lift the freeze. But Mr. Trump did not specifically mention the hold, and instead asked Mr. Zelensky to look into Mr. Biden and his son and into supposed Ukrainian involvement in the 2016 election. Among those listening on the call was Mr. Blair.

Mr. Blair has told associates he did not make much of Mr. Trump’s requests during the call for the investigations. He saw the aid freeze not as a political tool, but as an extension of Mr. Trump’s general aversion to foreign aid and his belief that Ukraine is rife with corruption.

Just 90 minutes after the call ended, and following days of email traffic on the topic, Mr. Duffey, Mr. Sandy’s boss, sent out a new email to the Pentagon, where officials were impatient about getting the money out the door. His message was clear: Do not spend it.

“Given the sensitive nature of the request, I appreciate your keeping that information closely held to those who need to know to execute the direction,” Mr. Duffey wrote in his note, which was released this month to the Center for Public Integrity.

This caused immediate discomfort at the Pentagon, with a top official there noting that this hold on military assistance was coming on the same day Ukraine announced it had seized a Russian tanker — a potential escalation in the conflict between the two nations.

On that same day, Mr. Sandy, having received the go-ahead from the budget office’s lawyers, took the first official step to legally impose what they called a “brief pause,” inserting a footnote into the budget document that prohibited the Pentagon from spending any of the aid until Aug. 5.

By that point, officials in Ukraine were getting word that something was up. At the same time, the effort to win a commitment from the Ukrainians for the investigations sought by Mr. Trump was intensifying, with Mr. Giuliani and a Zelensky aide, Andriy Yermak, meeting in Madrid on Aug. 2 and the diplomats Mr. Sondland and Mr. Volker also working the issue.

And inside the intelligence community, a C.I.A. officer was hearing talk about the two strands of pressure on Ukraine, including the aid freeze. Seeing how they fit together, he was alarmed enough that by Aug. 12 he would take the extraordinary step of laying them out in detail in a confidential whistle-blower complaint.

A ‘POTUS-level Decision’

Keeping a hold on the assistance was now a top priority, so officials moved to tighten control over the money.

In a very unusual step, the White House removed Mr. Sandy’s authority to oversee the aid freeze. The job was handed in late July to Mr. Sandy’s boss, Mr. Duffey, the political appointee, the official ultimately responsible for apportionments but one who had little experience in the nuts and bolts of the budget office process.

As the debate over the aid continued, disagreements flared. Two budget office staff members left the agency after the summer. Mr. Sandy testified that their departures were related to the aid freeze, a statement disputed by budget office officials.

Pentagon officials, in the dark about the reason for the holdup, grew increasingly frustrated. Ms. McCusker, the powerful Pentagon budget official, notified the budget office that either $61 million of the money would have to be spent by Monday, Aug. 12 or it would be lost. The budget office saw her threat as a ploy to force release of the aid.

At the White House, which had been looped into the dispute by the budget office, there was a growing consensus that officials could find a legal rationale for continuing the hold, but with the Monday deadline looming, it was a “POTUS-level decision,” one official said.

Complicating matters, another budget battle was escalating. Mr. Vought was attempting to impose cuts of as much as $4 billion on the nation’s overall foreign aid budget. It was an entirely separate initiative from the Ukraine freeze, and was quickly abandoned, but helped the White House establish that its concern about aid was not limited to Ukraine.

By the second week of August, Mr. Duffey had taken to issuing footnotes every few days to block the Pentagon spending. Office of Management and Budget lawyers approved each one.

Mr. Trump spent the weekend before the Pentagon’s Aug. 12 deadline at Bedminster, his New Jersey golf resort.

In a previously unreported sequence of events, Mr. Mulvaney worked to schedule a call for that day with Mr. Trump and top aides involved in the freeze, including Mr. Vought, Mr. Bolton and Pat Cipollone, the White House counsel. But they waited to set a final time because Mr. Trump had a golf game planned for Monday morning with John Daly, the flamboyant professional golfer, and they did not know how long it would take.

Late that morning, Ms. McCusker checked in with the budget office. “Hey, any update for us?” she asked in an email obtained by Center for Public Integrity.

Mr. Duffey was still waiting for an answer as of late that afternoon. “Elaine — I don’t have an update,” he wrote back. “I am attempting to get one.”

The planned-for conference call with the president never happened. Budget office lawyers decided that Ms. McCusker had inaccurately raised alarms about the Aug. 12 date to try to force their hand.

In Bedminster with Mr. Trump, Mr. Mulvaney finally reached the president and the answer was clear: Mr. Trump wanted the freeze kept in place. In Washington, the whistle-blower submitted his report that same day.

The National Security Team Intervenes

Inside the administration, pressure was mounting on Mr. Trump to reverse himself.

Backed by a memo saying the National Security Council, the Pentagon and the State Department all wanted the aid released, Mr. Bolton made a personal appeal to Mr. Trump on Aug. 16, but was rebuffed.

On Aug. 28, Politico published a story reporting that the assistance to Ukraine had been frozen. After more than two months, the issue, the topic of fiery internal debate, was finally public.

Mr. Bolton’s relationship with the president had been deteriorating for months, and he would leave the White House weeks later, but on this front he had powerful internal allies.

On a sunny, late-August day, Mr. Bolton, Mr. Esper and Mr. Pompeo arrayed themselves around the Resolute desk in the Oval Office to present a united front, the leaders of the president’s national security team seeking to convince him face to face that freeing up the money for Ukraine was the right thing to do. One by one they made their case.

“This is in America’s interest,” Mr. Bolton argued, according to one official briefed on the gathering.

 “This defense relationship, we have gotten some really good benefits from it,” Mr. Esper added, noting that most of the money was being spent on military equipment made in the United States.

Mr. Trump responded that he did not believe Mr. Zelensky’s promises of reform. He emphasized his view that corruption remained endemic and repeated his position that European nations needed to do more for European defense.

“Ukraine is a corrupt country,” the president said. “We are pissing away our money.”

The aid remained blocked. On Aug. 31, Senator Ron Johnson, Republican of Wisconsin, arranged a call with Mr. Trump. Mr. Johnson had been told days earlier by Mr. Sondland that the aid would be unblocked only if the Ukrainians gave Mr. Trump the investigations he wanted.

When Mr. Johnson asked Mr. Trump directly if the aid was contingent on getting a commitment to pursue the investigations, Mr. Johnson later said, Mr. Trump replied, amid a string of expletives, that there was no such demand and he would never do such a thing.

Around the same time, White House lawyers informed Mr. Trump about the whistle-blower’s complaint regarding his pressure campaign. It is not clear how much detail the lawyers provided the president about the details of the complaint, which noted the aid freeze.

Mr. Trump was scheduled to travel to Poland on Sept. 1 to commemorate the 80th anniversary of the outbreak of World War II, and had planned to get together with Mr. Zelensky. Some administration officials hoped meeting the new Ukrainian president in person would change Mr. Trump’s mind.

But a hurricane was bearing down on the United States, and Mr. Trump sent Vice President Mike Pence in his place. When Mr. Zelensky raised the issue with the vice president, Mr. Pence said he should speak with Mr. Trump.

Behind the scenes in Warsaw, Mr. Sondland, the American envoy who was Mr. Trump’s point person on getting the Ukrainians to agree to the investigations, had a blunter message. Until the Ukrainians publicly announced the investigations, he told Mr. Yermak, the Zelensky adviser, they should not expect to get the military aid. (Mr. Yermak has questioned Mr. Sondland’s account.)

An Abrupt Reversal

By late summer, top lawyers at the budget office were developing a proposed legal justification for the hold, based in part on conversations with White House lawyers as well as the Justice Department.

Their argument was that lifting the hold would undermine Mr. Trump’s negotiating position in his efforts to fight corruption in Ukraine.

The president, the lawyers believed, could ignore the requirements of the Impoundment Control Act and continue to hold the aid by asserting constitutional commander in chief powers that give him authority over diplomacy. He could do so, they believed, if he determined that, based on existing circumstances, releasing the money would undermine military or diplomatic efforts.

But divisions within the administration continued to widen; Mr. Bolton was opposed to using an argument proffered by administration lawyers to block the funding. And pressure from Congress was intensifying. Mr. Johnson and another influential Republican, Senator Rob Portman of Ohio, were both pushing for the aid to be released.

On a call with Mr. Portman on Sept. 11, Mr. Trump repeated his familiar refrain about other nations not doing enough to support Ukraine.

“Sure, I agree with you,” Mr. Portman responded, according to an aide who described the exchange. “But we should not hold that against Ukraine. We need to release these funds.”

Democrats in the House were gearing up to limit Mr. Trump’s power to hold up the money to Ukraine, and the chairmen of three House committees had also announced on Sept. 9 that they were opening an investigation.

Still, White House officials did not expect anything to change, especially since Mr. Trump had repeatedly rejected the advice of his national security team.

But then, just as suddenly as the hold was imposed, it was lifted. Mr. Trump, apparently unwilling to wage a public battle, told Mr. Portman he would let the money go.

White House aides rushed to notify their counterparts at the Pentagon and elsewhere. The freeze had been lifted. The money could be spent. Get it out the door, they were told.

The debate would now begin as to why the hold was lifted, with Democrats confident they knew the answer.

 “I have no doubt about why the president allowed the assistance to go forward,” said Representative Eliot L. Engel, Democrat of New York and the chairman of the House Foreign Affairs Committee. “He got caught.”