In the late spring of 2015, I was ushered into the West Wing office of President Obama’s head speechwriter. An intern paying my respects to the boss’s boss, I made my way three chambers deep into the basement sanctum. Like any good pilgrim, I sought something nearly inarticulable from a higher power—absolution, validation, or a cure. During the meeting, out came the relics: Obama’s famous yellow legal pads containing his Nobel Prize speech drafts as well as the more mundane next day’s remarks with his scribbled notes. 

Obama’s memoir A Promised Land written in that same long-hand on those same yellow legal pads, marks his latest salvo in the ongoing contest over his legacy and our psyches. “More than anyone,” Obama writes, “this book is for those young people.” But for the generation that came into political consciousness around 2008, reckoning with Obama’s sway over us—and his language that captured us—involves an investigation of our own personal ideologies. 

We might remember being caught up in the magic of his speeches, on the other end of what Obama calls “a physical feeling, a current of emotion that pases between you and the crowd.” I still remember sitting alone in front of the TV, my teacher parents having gone to sleep early, watching Obama concede the New Hampshire primary in January 2008 while announcing, “yes we can.” Since then, many of us have drifted out of his wake, to the left of those who defend his compromises: Pod Save America, Pete Buttigieg, and their corporate sponsors. Reckoning with Obama means at least partially breaking the spell, an unlearning that requires both some measure of critique and self-critique of our own rapture.

My personal devotion landed me an internship for several months on the very outer edges of the writers’ circle churning out a half-dozen speeches a week for Obama, the First Lady, and occasionally other officials—a veritable bimonthly literary magazine of speeches. Ahead of a St. Patrick’s Day reception with the prime minister of Ireland, I read Yeats all day on a bench for one useful line. I rushed across the Mall to deliver books. I called high school White House Science Fair participants for details on their projects. Ahead of Michelle Obama’s Tuskegee commencement, I visited the Library of Congress’s microfilm desks to rustle up a first-person narrative from a trailblazing Black airman. I didn’t get close to meaningfully writing—mostly I gave tours on behalf of busy staffers and researched choice quotes and facts. Then I watched the President read my quotes and facts on TV or, if I was lucky, from the back of the East Room.

Seen from the perspective of the White House, I was slightly more useful than a gadfly to an operation that had been running well for six years; but that meant I could see partially from the outside. A speechwriter called me something like “incredibly pretentious,” when I slipped into the Maori pronunciation of “Samoa.” Then I walked back to my desk through halls where every piece of art was a photo of the first family. I was drowning, in good ways and bad, in the proximity to power—the intelligence, the skill, and Obama’s cult of personality.

As a speechwriting intern and, earlier, an Obama devotee—after his inauguration, a “Yes We Can” poster hung in my college dorm room—I’ve increasingly come to terms with a characteristic of Obama’s ideology I’d describe as the banality of merit: the belief in the inevitable bending of the moral universe toward justice based on qualified people doing hard work well. Subprime lenders were immoral because they were incompetent, reckless. Same with the Bush bureaucrats who designed the Iraq War. 

In terms of messaging, a specific story with factually correct research and precisely chosen words simply makes a good speech. So judging an Obama speech involved a sort of modernist sensibility—not language of impact, but turn of phrase, not a speech of purpose but of execution. Obama’s 2009 joint address to Congress on healthcare, which “according to poll data… boosted public support for the [Affordable Care Act],” serves as barely an exception that proves the rule. Like Auden’s line about poetry, very rarely did Obama’s words make anything happen. 

Ahead of his remarks on the 50th anniversary of the Selma marches, where Obama more clearly articulated his vision of American exceptionalism than in maybe any other text, I pulled dozens of quotes from the American literary canon. One Emerson line entered the speech; it comes from “Nature,” a text I now teach to first year college students: “we are never tired so long as we can see far enough.” For Obama, Emerson describes the alignment of optimism and ambition—seeing far, then working hard, leads inevitably to doing good. Far-seeing people working diligently at competitive jobs not only produces top-notch speeches, it serves as the main necessary engine for progress. As Obama writes in his memoir’s second paragraph: “for all its power and pomp, the presidency is still just a job.” 

But in its full context, Emerson describes something more like the zig-zagging movement of a tacking ship, contingent on uncertainties, and the hopeful, yet terrifying, characteristic of not seeing past the horizon; what might as well be America’s flirtation with fascism or a millennial’s career trajectory. Obama prefers a metaphor that may seem more complex at first but is really much simpler than Emerson’s: the federal government as “a big ocean liner.” The phrase appears in press conferences throughout Obama’s tenure, from the 2009 economic recovery to Donald Trump’s election, and again in this book—the behemoth of government (or better, society itself) nudged in the direction of progress by its qualified helmsman. For Obama, station the most meritorious person at the wheel and voilà, the Whiggish slide toward enlightenment freedoms ensues. 

The problem, of course, lies in where one steers the ship or bends the arc—a process never as clean as these metaphors imply. Obama knows this, and the weight of these choices results in what Carlos Lozado calls “on-the-other-handedness,” or what Chimamanda Ngozi Adichie jokes with her friend is “doing an Obama.” But that’s almost too generous. Eschewing the label “revolutionary” in favor of “reformer, conservative in temperament if not in vision,” the book shows a man even more trusting of the inevitability of incremental progress than the latter word implies: conservative in vision, also. Obama admonishes readers to be grateful he didn’t put bankers in jail, restructure Wall Street, or bail out homeowners; anything like that “would have required a violence to the social order, a wrenching of political and economic norms, that almost certainly would have made things worse.” 

Would bigger changes really have made things worse? Many former officials regret not thinking bigger. Weeks into his reign as Obama’s centrist successor, even Joe Biden himself worries less about overthinking than about thinking too small. In a response to Larry Summers warning that the 2021 stimulus would produce a violence to the social order, Biden reverses the Summers/Obama fear: “One thing we learned is, you know, we can’t do too much here … We can do too little. We can do too little and sputter.”

Obama actually pushed back in a Washington Post interview against both Lozado and Adichie, defending “overthinking” as a virtue. But the problem wasn’t that he saw both sides, it was that he saw too few. The examples of creative, progressive policies Obama did not pursue are myriad: leveraging aid to stop Israel’s annexation of the West Bank (something even Buttigieg supported), the Warren campaign’s signature wealth tax, Booker’s baby bonds, Castro’s repeal of Section 1325 criminalizing immigration, not to mention Sanders’s housing-for-all, universal pre-K, and many more. When one lets the experts of the system fix the system, we’ll never know about all the “other hands” that never came up.

A too-deep belief in gradualist, institutional merit eliminates both external creativity and also external tests of virtue. It’s the same logic that allows Obama to list Rahm Emmanuel’s Wall Street connections as a reason to tap him for chief of staff as opposed to a reason not to. It’s also why a decade later, Obama interns and staffers seem less likely to be community organizers, union leaders, or non-profit workers than consultants, bankers, and staffers for corporate Democrats. See, for example, the exodus of high-up staffers to Big Tech: David Plouffe (Uber), Lisa Jackson (Apple), and Eric Holder (Airbnb), among others. By such a merit-obsessed ethic, the fact that a gig at McKinsey or Lyft is more competitive than one in a public school means the former are better morally. And so as much as the effect of Obama’s ideology may have inspired a generation, it also diverted much of that ethical impulse into meritocratic ladder-climbing.

Obama’s own career turned from organizing to Harvard, from social movements to institutions. Over and over again his person and policies become a sort of lightning rod by which the energy of outside agitation could be diverted and subsumed by the current order. At each of these pivotal moments in his biography, Obama wonders whether he was “driven not by some selfless dream of changing the world but rather by the need to justify the choices I had already made, or to satisfy my ego.” An ideology of merit easily solves this particular problem because it encourages self analysis but discourages hard choices. It’s banal because the question solves itself; the most ambitious, meritorious track is always necessarily the most righteous. 

As late as 2015, despite Occupy Wall Street and the unending war in Afghanistan, for me the shine remained. Obama had prevented the second Great Depression, passed healthcare reform, and ended the Iraq War after all, and over time he had gotten better at explaining his achievements, though it cost him a bit of his fire. And at the very least, those speeches I assisted on in those small ways overflowed with science, history, and culture, probably more than any president we’ll see in our lifetimes.

But of course even then I had my doubts. As Obama describes Dodd-Frank, in a line that can stand for his accomplishments overall: it was “more a matter of bad outcomes prevented than tangible benefits gained.” So it’s almost cliche now to mention Obama’s deportations, the problems with Obamacare, and a foreign policy that, metonymically, drew down Guantanamo while leaving it open. But by the ideology of merit, Obama succeeded. He hired top corporate and political apparatchiks, managed the bureaucracy, and “did the work.” As long as the ocean liner remained on course, the shortcomings of specific policies were beside the point. 

Even with all that “catastrophe averted” and culture added, Obama’s crisis messaging, by his own account, “failed to tell the American people a story they could believe in.” Here Obama offers the most honest self-analysis in the entire book. Unlike FDR, he hadn’t “understood that to be effective, governance couldn’t be so antiseptic that it set aside the basic stuff of politics.” Of course, what Obama sees largely as a messaging failure, to me remains a policy one. Try as he might to justify his defensive incrementalism, I’m not convinced a better future couldn’t have been achieved: a public option, more direct-to-people bailouts, and a less militarized foreign policy. As his mother-in-law and barber ask: “where’s my bailout?”

So by 2017, after the dust settled on Trump’s election, and I was forced to buy outrageously expensive health insurance on Obama’s exchange, I had also finally become more convinced that by his own standard of FDR, Obama failed not only in messaging but also on ideas. Maybe my own interest in that internship had been guided by this exact, banal logic: merit as ethics. With my Yes We Can poster now rolled up in a closet, I realized, ironically, that Obama’s was a failure of imagination.

As Obama walks down the colonnade at the start of his memoir’s first chapter, he meets an old White House groundskeeper named Ed Thomas. Thomas, like every character I’ve encountered in an Obama text, is respectable not because of his humanity but because he does a job. When Obama asks Thomas, who’s been in that role for 40 years, how long he plans to stay on before retiring, of course he answers, “I don’t know, Mr. President… I like to work.” In other words, not quite “work sets you free,” rather “work makes you good.” For Obama, Thomas is deemed worthy by virtue of his job.

But I wonder what kind of world we could imagine if, when we ask, as Obama does at the height of the economic crisis, “who, exactly, was deserving of government assistance?” we simply answered “everyone.”