My Complicated Relationship with Barack Obama

Rarely has a man promised so much but offered so little. Let's call it what it is—a tragedy.

I was sharing some thoughts about President Obama last week which got a lot of people riled up—not against me but against Obama. You can decide for yourself if it was deserved, or whether I was being overly harsh about a flawed man. In light of the recent controversy around David Samuels’ feature on Obama in Tablet, it seems like there’s renewed interest in his legacy. Who was he, really? And how should we remember him?

This led me to go back to Obama’s presidential memoir A Promised Land, and part of me still couldn’t believe certain passages. Here, for instance, Obama is discussing drone warfare, and it strikes me as one of the most callous statements I've ever come across in any memoir. Note the use of the passive voice in the final sentence.

The great tragedy of Obama is that his presidency now seems small and inconsequential, so much of his legacy dismantled and discarded, not just by his opponents but by his supporters too. He will be remembered largely for what might have been but wasn’t. Instead of heralding a new kind of a “post-ideological” politics, Obama’s eight years were a prelude to the return of ideological conflict that we now, sadly, take for granted.

Because Obama, today, seems so out of place and out of time, it can feel gratuitous to pay too much attention to his legacy. After all, we’ve got pretty big problems these days. One of them is named Trump. But this is a cop-out. If the current era of American politics is, at least in part, a product (or result) of what came before, then we should understand what came before, even if it casts a would-be savior in a less flattering light.

With all of this this in mind, I want to share an old post from 2021 about my complicated relationship with Obama, beginning from my time as a young, impressionable graduate student. Like all of the older essays in our deep archive, this one is paywalled. But as a way of saying thank you—and in the hope of perhaps even entertaining you—we’re unlocking the piece below for your reading pleasure.

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And now to the piece.

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I have a complicated relationship with Barack Obama. I wish it were otherwise. Trust me, I wanted to believe. In 2008, my roommates and I hosted a modest "fundraiser" for him in our apartment. It was, I suspect, mostly an excuse for a party. But we were excited, probably too excited in retrospect. To fall in love with a candidate—and to persist in this love, both unequal and unrequited—is to tempt fate as a scorned lover. I realize that I'm perhaps unfairly harsh on Obama, as my mom often reminds me. She (still) loves him. This is a point of tension. My brother, meanwhile, thinks that my problems with Barack Obama led me to be too soft on Donald Trump, who, he argues correctly, was a much worse president. These are all valid points, and I will not refute them here.

I've tried to be better. I want to be better. With this in mind, I tried to put off reading Obama's (third) memoir for as long as possible. I didn't want to invite back the darkness. I had been behaving myself, and not bringing up Obama with any frequency. For the book I'm finishing now, however, I didn't have a choice. My account would be incomplete otherwise. The struggle is real.

Even the title was grating. Who calls their own memoir A Promised Land? Barack Obama, that's who! But I had a duty, and duty called.

The first thing I noticed was the self-regard masked as self-awareness, a clever trick that apparently went down well with most mainstream reviewers who, when they did offer gentle criticism, did so with sufficient reverence. After all, he wasn't Donald Trump!

The surprisingly bad prose aside, the frustrating thing about Obama is that at times he basically sounds like me (or any critic of Arab autocracy). For example, he seems to understand that autocracy, by definition, isn't permanent. He recalls telling a senior aide early in his first term that "sometime, somewhere, things are going to blow." Despite this knowledge, he spends several years doing almost nothing about it. Now that I think about it, Obama would make a good think tank analyst. But Obama wasn't a think tank analyst. He was the president of the United States of America.

In a recent Friday Essay, in a more generous mood, I wrote about Obama's hypocrisy in contrast to Trump's "anti-hypocrisy," coming down firmly on the side of the former. Obama 1, Trump 0. Still, there is the danger of being not just good, but too good. And sometimes I get the sense that Obama imagines himself as an intensely moral man. He is always "wresting" with dilemmas, profoundly in touch with his own conscience. When he is in the right mood—and, yes, he describes caring about human rights abroad as one of his "moods"—he calls up Samantha Power and feels morally superior as a result, because he has listened to Samantha while also apparently ignoring everything she has to say. The world is "messy," he reminds us, and this, too, is evidence of having wrestled with the responsibilities of power. (Obama's dismissiveness toward Samantha Power is cringe-inducing. He basically treats her like a little kid—a native, emotional, and formerly "young" person, unschooled in the ways of the world, who cares about those pesky things called human rights. Power returns the favor by suggesting that she was "educated" as a result of serving under a man as great as Obama.)

Obama is also keen to remind us, at seemingly every opportunity, not of how amazing his presidency actually was, but of how amazing the idea of his presidency was. This sometimes reaches comical effect, as when he goes, in one short breath, from "the idea of America" to...himself.

It appears that Obama cannot disentangle these two things. He is the embodiment of what America might become, and perhaps what it already was (at least during his eight years as president, if not necessarily the subsequent four). If you, yourself, are the literal realization of the American idea, proof that the arc of history bends toward justice, then you are likely to perceive attacks on yourself as attacks against the country. Here, too, Obama does not disappoint, seemingly unable to appreciate that criticisms from Democrats, Republicans, or even Europeans may occasionally be legitimate and emerging from a place of good faith. "Not everyone is out to get you!" I want to scream as I thumb past yet another page replete with false humility.

It is evident that Obama wishes to be regarded by history in the pantheon of his heroes. One of them is Czech dissident turned president Vaclav Havel. During a brief meeting in April 2009, Havel, in an unlikely coincidence, reassures Obama the way Obama often reassures himself. “You’ve been cursed with people’s high expectations," Havel tells him. "Because it means they are also easily disappointed. It’s something I’m familiar with. I fear it can be a trap.” One can imagine Obama dutifully nodding at this pearl of wisdom, one that would relieve him of the immense responsibility bestowed upon him by the adoring masses. Among other things, A Promised Land is the story of a man who was doomed by his own greatness. Oh, the audacity!

Havel, it turns out, was correct. People turn on you. It's a trap. And, yes, they are easily disappointed.

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