The Five Best and Five Worst Things About the Obama Presidency

With just a handful of days until Donald Trump is president, now is the perfect time to take stock of the Obama presidency—good and bad.

Joshua Lott/Getty Images

Back in December, it was possible to pretend this week would somehow never come. But here it is. Donald Trump is going to be the president of the United States. And Barack Obama is going to give that final salute as he steps aboard Marine One. Well, maybe he won’t be coptering, since he’s only going to Kalorama. But you know what I mean. It’s going to be a devastating day.

I’ll get to the Trump half of this hand-off later this week, but for now, let’s think about Obama. What will his legacy be?

Below, I’ll list what I think were Obama’s five greatest successes and his five biggest whiffs. That’s just for the sake of symmetry, but you shouldn’t take it to mean I think he batted .500. I think his average was a lot higher than that. If he wasn’t a great president, it’s mainly because our polarized times, and the corruption of so many of our institutions into naked instruments of partisan pursuit (hello, FBI), prevented him from achieving a formidable enough list of accomplishments to be considered great. When the other party gives you virtually no votes on anything, openly vows to make you a one-termer, and doesn’t accept your fundamental legitimacy as president, you’re not going to put a second New Deal in place.

In a different time, before the Republican Party became so radical and obstructionist, Obama would indeed have been a great president. He would have liked nothing more than to have 12 or 15 Senate Republicans with whom he could negotiate and solve the big problems, as Lyndon Johnson did. But he didn’t. What he did, he had to do with no Republican help at all--and then, after refusing to negotiate with him, the Republicans turned around and accused him of being the partisan one! Nice work if you can get it.

So I therefore rate him a very good, not quite great, president. I think time will be kind to him. And if the next four years go like we have reason to fear they will, time will be a lot kinder to him a lot sooner than we may now think.

So, here are five hits and five misses. First, the good, in reverse order:

5. The Affordable Care Act. Yes, lots of people’s premiums and deductibles are too high, and certain small businesses legitimately find it burdensome. Those are things that can be fixed over time, if the law survives, which frankly I doubt.

Still, it was a landmark achievement. It has helped millions, and in the states that actually put effort into its implementation, it’s done well overall. Even if the Republicans dismantle it, Obamacare has accomplished one important thing: Everyone now agrees that Americans should not be denied health coverage because they’re sick. That’s something many other countries agreed on long ago, and it’s a wholly positive legacy no matter what happens.

4. Economic Recovery. This wasn’t as great as we might have liked, but considering we were losing 600,000 jobs a month when he took office, he did all right. Job creation during his tenure clocks in at 11.3 million, ranking him third among recent presidents. There’s Dodd-Frank—far from perfect, but a law that’s done much good, especially the Consumer Financial Protection Bureau. And there’s the auto bailout, which has been a magnificent success. Wage stagnation is a big problem, but it’s one that well predates Obama.

3. The Cuba Opening. It’s hard to say how this will go down. I hope and suspect that the newfound exposure to capitalism will, over time, bring Fidelismo to heel. But whatever happens, it was a bold step, the best example of Obama’s impatience with antiquated thinking. This was something the United States should have done 20 years before.

2. Getting Osama bin Laden. It amazes me that most people still don’t know this detail about the raid, but if what Leon Panetta wrote in his memoir is accurate—and I’ve seen no one challenge it—then Obama deserves even more credit for this than just having ordered it. As the plans for the raid were being laid out to him, Obama suggested adding two backup helicopters to the mission. Sure enough, the lead copter malfunctioned. If those two backups Chinooks hadn’t been there, the United States would have suffered a major humiliation and Obama probably never would have recovered. Not bad for a guy who supposedly hates the military.

1. Just Being Dignified. He—and his rather incredible wife—always comported themselves with dignity, always honored the office. Some liberals complain that he did this to a fault, especially recently, giving Trump far more deference than he deserves for the sake of ensuring the peaceful transition of power. Maybe that’s so, but I’d rather have a president err on the side of having too much honor. We’ll soon see what the opposite is like.

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Corollary good deed here: A scandal-free White House for eight full years. (I mean actual scandals, not right-wing “scandals.”) That’s a really hard thing to do. I think it’s tied to the dignity with which he and Michelle carried themselves: People want to emulate the boss.

OK. Now the negative:

5. Overplaying His Hand With Bibi Early On. This has nothing to do with the merits of Obama’s position on the settlements, but too much pressure too soon on Netanyahu started a downward spiral in the dynamic that could never be fixed. Democrats in Congress came to Bibi’s defense publicly and privately, and Obama was isolated against Likud and its bipartisan supporters. Bibi trolled him to death in subsequent years—but only because he knew he could.

4. Appointing Jim Comey to Head the FBI. Yes, a little benefit-of-hindsight at work here, but the issue of why Democratic presidents keep allowing it to be accepted as a truism that the FBI director has to be a Republican has been an issue at least since Bill Clinton named Louis Freeh to the job. And it did raise some eyebrows at the time. The historian Rick Perlstein wrote three columns about what a mistake it was for Obama to name Comey (here’s one of them).

3. Not Being Tougher on the Banks. Again, there’s a hindsight at work here. Very few people had any sense in 2009-2010 that we’d be living through this anti-banker populist anger in 2015-2016. And it’s also the case that when Obama did tut-tut Wall Street, even with pretty light rhetorical barbs, they responded by whining in a way that, say, brown people would never, ever be permitted to whine about immigration laws. Still, Obama should at the very least have made an example of just one guy, just one firm.

2. Being Way Too Naïve for Way Too Long About How Obstructionist and Extremist the GOP Had Become. I hardly need elaborate on this. I came to hate hearing him say “I look forward to working with my Republican friends” on whatever it was.

1. Syria. This is easily number one, sad to say, and I think his (non-)handling of the crisis in Syria will go down as the only really big black mark on his record. The false “red line”; I knew the second I heard him say that in 2012 that it was going to lead to a disaster of one kind or another. And while it’s true that any escalation risked further escalation, I think that’s a lesson that liberals sometimes overlearn, or lean on too hard. We could have done more for the moderate rebels back when they were putting up a good fight.

Obama did less on Syria than he might have in part because of the Iran deal, which is why unlike most liberals I don’t list that deal as among his high achievements. Too many Syrian lives were sacrificed to that deal. It was (and remains) a very complicated situation, but the bottom line will always be that the West watched this slaughter happening and did little. Not nothing. But little.

So that’s one he can’t escape. But let’s go back to a happier note before we close this out. I think back to election night, 2008—the history-making nature of it, the optimism after eight years of bumbling and darkness. Obama hasn’t lived up to every expectation. Who could? But while I disagreed with some of his decisions and was deeply frustrated by some others, there was never a moment in the last eight years when I looked at him and thought, “I’m ashamed that guy’s the president.” Usually quite the opposite in fact. So you bet I’ll miss him, and I’m pretty sure that after they get a gander at the alternative, most Americans will.