First of all, it is axiomatic in our politics that we look back at previous presidents we opposed and soften our views, particularly in comparison to the current one. It was during W's administration that we started hearing the "Reagan couldn't get elected in today's GOP" takes, and under Obama the right suddenly found lots of things they liked about Clinton (at least until his wife started running). I guarantee you that in a few years (hopefully two), the right will discover Obama's virtues relative to that dastardly President Harris. (In fact, it scares the hell out of me to realize that 15 years from now, I may be saying, "Compared to President Ted Nugent, Trump wasn't actually that bad.") So with all of those biases in mind, I will try to give you my honest assessment of Bush.
On a personal level is probably where I've softened the most. Fifteen years ago I would have told you he was an SOB based on things like how he treated McCain in 2000 and just his overall demeanor of a spoiled rich kid who, to borrow a phrase Jim Hightower used to describe Bush Sr., "was born on third base and thinks he hit a triple." A couple things have caused me to revise that assessment. One, it's become clear that he had a deep respect for the institution of the presidency. Two, whatever his policy choices after 9/11, his refusal to demonize Muslims was praiseworthy (though again, that's probably the kind of thing that stands out more in comparison to Trump). Finally, his behavior since leaving the White House has been exemplary. In that respect, I would compare him favorably to Bill Clinton and (especially) Jimmy Carter, who has done a tremendous amount of good in terms of charity but also seems at times like he resents whoever is currently in the White House and still thinks he could do a better job.
In terms of policy, I'll start with the good things: A decade ago I used to have a group of friends that I'd get breakfast with every couple weeks and talk politics. For our breakfast on the day of Obama's inauguration, the ground rules were that even though we were all liberal Democrats, we had to find nice things to say about Bush. The main things we came up with were PEPFAR, which really did do a lot of good in Africa, and more generally, Bush's tacit recognition during his second term that he had screwed up a lot foreign-policy wise and needed to dial things back a little: Condi as SoS, sidelining Cheney and Rumsfeld, etc. For a guy who was generally thought of as too stubborn to admit his mistakes, he deserves some credit for that recalibration. As for the surge in Iraq, I opposed it at the time, and I think a good chunk of its success was attributable to the "Sunni Awakening" already underway that led to more mainstream Sunni groups turning on al-Qaeda in Iraq, but overall the situation did improve there in 2007-08, so I give him some credit.
But of course the decision to go into Iraq in the first place was a monumental strategic error, one of the greatest in American history, and ultimately contributed to the Syrian civil war and ISIS, the refugee crisis, etc. It's hard to overlook that just because he did an OK job minimizing some of its failures a few years later. And yeah, maybe he got manipulated by Cheney in that respect, but of course he was the one who picked Cheney, so that's on him as well.
Economically speaking, the tax cuts were a horrible idea that turned a deficit into a surplus without delivering much of the promised economic benefits, the prescription-drug benefit was a massive giveaway to Big Pharma, and while he didn't directly cause the real-estate meltdown, it was a consequence of years of right-wing ideology. (One more thing I give him credit for: after initially appointing a couple of weak hacks as his first two Treasury Secretaries, he came to the belated realization that he needed a smart guy in that role, and basically gave Hank Paulsen the keys to the castle. Even better, Bush was smart enough to get out of Paulsen's way during the financial crisis. I don't agree with everything Paulsen did, but we were on the knife's edge and things could have gotten much worse than they did. The thought of Larry Kudlow and Steven Mnuchin muddling their way through a similar crisis under Trump gives me the heebie-jeebies.) And oh yeah, let's not forget Katrina. The hurricane itself obviously wasn't his fault, but he completely botched the response, mostly because he had an unqualified hack as head of FEMA.
Overall, presidencies are generally judged by whether they delivered peace and prosperity, and Bush did neither. So I don't see how you can describe his presidency as anything other than a failure. But on a visceral level, I'm not nearly as mad about it now as I was at the time.
