I think he's the most disappointing. If he wasn't such a petty little piece of dung he really could have done some powerful and amazing things during his tenure.
Take what's happened in places like Ferguson. That could have been his moment to bring us together, to bridge gaps between us. Instead, he chose to use it as a wedge issue. And that's what I find most disappointing about him. He wants us to fight, to be at each others throats. Rich vs. Poor, men vs. women, black vs. white, black vs. cops...name an issue and he's front and center, gleefully dividing us.
But lets not confuse Obama being a despicable and loathsome human being with him being the worst president ever. "W" was a really nice guy, but completely overwhelmed by the office and was a 'placeholder' President at best. When ranking our Presidents the likeability factor shouldn't be a factor. It's what they were elected to do, and what they actually did.
I'm on record as saying I fell for the Obama BS the first time around. I was captivated by the thought of someone coming in and spearheading 'the most transparent administration ever'. Instead I got......this. Never in the history of the presidency has someone abused the office as much and returned so little to the people. I could get into the Executive Orders, Fast and Furious, etc....but they've been done to death on this board already. His administration has done some truly awful and unforgivable things. Terms like underhanded and shady are well deserved. The spying on Americans, using the IRS to crush your political enemies, the Benghazi debacle...the litany of his moral crimes against the American people is staggering. History will not be kind to his time in office.
But I still get back to 'disappointing'. With just a teaspoon of sugar he could have truly transformed this country. During his first term, he had a built in cabal of Republicans (including the nominee he beat) that would have voted alongside him on all kinds of things. With even a LITTLE ego stroking he would have had them in the palm of his hand, providing "bi-partisan cover". Instead, he chooses to be a peacock ##### instead of a deal maker. He scorches the earth into two sides, "with me" or "against me".
A lot of people like to crack on W as a bad president, but I never got the impression that he felt he wasn't the President for all of the American people. He was a lot like Jimmy Carter in that regard. So was Bill Clinton. If Obama had even PRETENDED to be that guy he had a willing partner in the media to spread his message to the masses. But he was only interested in being the President for people on "his side".
If you're not on the Obama side of the fence, you're considered the enemy. But if you're on the Obama side of the fence, the taxpayer money flows to even the most worthless of projects (Solyndra) or protects the most racist of causes (DOJ sweeping the Black Panther voter intimidation crimes under the rug). By definition, if you're on "the other side", everything you want or do is obstructionist and wrong. I hate how he's divided us. I've lost good friends because of this....man.
He's a bad guy and a horrible leader. His lack of intellectual curiosity and inability to learn from his mistakes is troubling. He's ignorant of how the economy works, and doesn't seem all that interested in learning how it does. He's turned America into a joke around the world with Obama as the punchline. He may have initiated foreign policies that we may never recover from (if Iran nukes Israel, the blood is ALL on Obama's hands).
So, is he the worst ever? Could be. All I know is a better case can be made that he's the worst than one for him being the best.