In anticipation of the release of Volume I of his presidential memoirs, Barack Obama published a playlist featuring some “memorable songs from my administration.” The selections seemed calculated to offend nobody. There was something for all tastes: Frank Sinatra, Bob Dylan, Beyoncé, U2, Gloria Estefan, The Beatles, Miles Davis, Brooks & Dunn, Fleetwood Mac, Stevie Wonder, Jay-Z, B.B. King, and even Eminem all had their place. Rock, country, Latin pop, R&B, hip hop, blues, jazz. At once popular, middlebrow, and ever-so-slightly refined. Nobody needed to feel neglected, everyone was included. The divides between Country America and Hip Hop America were bridged. Who could possibly criticize the playlist? It was utterly unobjectionable. Perfect. A collage of American heartland sounds. Aretha Franklin covering The Band’s “The Weight,” with Duane Allman on guitar—Southern rock meets Detroit gospel! What better proof that our divides are illusory, that red-blue and Black-white are artificial categories, that we are better off when we borrow from all traditions and recognize each other’s humanity? One cannot help but recall Matt Taibbi’s scorching 2007 description of Obama as a “an ingeniously crafted human cipher” whose “‘man for all seasons’ act is so perfect in its particulars that just about anyone can find a bit of himself somewhere in the candidate’s background.”

The playlist is therefore a fitting accompaniment to the book, A Promised Land, which covers the period from Obama’s early life up until the end of his first term. A Promised Land is not just a recounting of events, but a lengthy argument for the author’s political vision and an attempt to explain why he made the choices that he did. Notwithstanding its (mostly unconvincing) effort to appear self-critical and introspective, the book is as much a response to critics as a straightforward chronicle; a defense of a legacy, a record, and a political outlook whose detractors, on both left and right, have only grown more vociferous with the passage of time. Part memoir and part apologia, A Promised Land thus offers tremendous insight into how the most gifted and popular liberal politician in living memory sees the world—and the considerable limitations of his vision. From beginning to end, it proves an epic demonstration of Obama’s skills as a political storyteller, his remarkable knack for making the status quo appear novel and the calculated seem earnest. Above all else, it showcases his masterful ability to speak the language of conservatism in the register of idealism and progress. 

The Man from Everywhere and Nowhere 

Any fair critic of the author needs to acknowledge that he is an immensely talented writer. Just as he once dazzled crowds with flourishes of sonorous rhetoric, Obama here offers readers a style of prose completely atypical of the average political memoir. As legions of ghostwriters can attest, most politicians and public figures are ill-equipped to produce a single readable paragraph without conscripting a phalanx of uncredited wordsmiths in the effort. Even the more gifted and independently-minded among them would struggle to bring such literary flair to the often mundane business of governance, campaigning, and retail politics. In Obama’s hands, however, all three are seamlessly woven into a sweeping narrative tapestry in which very little seems labored or out of place. 

While they certainly include plenty of extraneous description—recounting, in forensic detail, the exact appearance of meeting tables at international summits (adorned with “a national flag, a microphone with operating instructions, a commemorative writing pad and pen of varying quality”) or lengthy taxonomies of various physical objects found in the Oval Office (“the busts of long-dead leaders and Remington’s famous bronze cowboy; the antique grandfather clock…the thick oval carpet with stern eagle stitched in its center, and the Resolute desk, a gift from Queen Victoria in 1880 ornately carved from the hull of a British ship that a U.S. whaling crew helped salvage after a catastrophe…”)—the 700 pages that make up A Promised Land are brimming with lyrical passages like the following description of the White House Rose Garden from the book’s opening chapter: 

“Oh, how good that garden looked! The shady magnolias rising high at each corner; the hedges, thick and rich green; the crab apple trees pruned just so. And the flowers, cultivated in greenhouses a few miles away, providing a constant explosion of color—reds and yellows and pinks and purples; in spring, the tulips massed in bunches, their heads tilted towards the sun; in summer, lavender heliotrope and geraniums and lilies; in fall, chrysanthemums and daisies and wildflowers. And always a few roses, red mostly but sometimes yellow or white, each one flush in its bloom.” 

Delivered from the fingertips of a Hillary Clinton or a John Kerry, the preceding description would probably hit with the cacophonous thud of an elbow smashing the keys on a grand piano; its imagery stale, its delivery mannered, and its rhythm a jarring staccato.* Wielded by Obama, however, even a description of the White House Rose Garden quickly turns into an epochal meditation on fatherhood, duty, longing, the passage of time, and the wondrousness of America—the author somehow evoking George Washington, Martin Luther King Jr., and Norman Rockwell’s 1946 oil painting Working on the Statue of Liberty in a single paragraph that follows (“The men in the painting, the groundskeepers in the garden—they were the guardians, I thought, the quiet priests of a good and solemn order”). 

“Wielded by Obama even a description of the White House Rose Garden quickly turns into an epochal meditation on fatherhood, duty, longing, the passage of time, and the wondrousness of America…”

There are numerous sections in this vein, the book leaping with ease across vast expanses of space, time, history, geography, ideology, and culture—from the battlefields of Gettysburg and Appomatox to the palace intrigues of ancient Egypt; from the jazzy rhythms of Manhattan’s Village Vanguard to the writings of Langston Hughes and Fyodor Dostoyevsky; from the cloistered world of White House cabinet deliberations to the open air retail politics of the Iowa caucuses. As elegant as his paean to the Rose Garden, Obama’s more literary passages ultimately achieve something else: the fusion of his thoughts and biography with anything and everything he finds around him. On a rhetorical level, the effect is incredibly potent, giving the impression of a thoughtful leader perpetually grappling with the infinite complexities and nuances of a world rendered in glorious technicolor. Aesthetically pleasing though it may be, this mode of storytelling does more to obscure than illuminate the author’s actual beliefs, its imagery and style being so polychromatic that anyone can, indeed, find their own preferences or tastes represented somewhere between the lines.

Obama’s choose-your-own-adventure schtick undeniably explains much about his popularity and appeal, a reality to which he himself seems exquisitely attuned. “I was new and unexpected,” the author writes of his rapid ascent from senator to president, “a blank canvas onto which supporters across the ideological spectrum could project their own visions of change.” Removed from their immediate context, in fact, parts of ​A Promised Land ​could almost be read as self-aware metacommentary on the nature of political cipherhood. Take the following passage, which comes early in the book amid a section about his early life reflections on hierarchies of race and class: 

“All of this pulled me in different directions. It was as if, because of the very strangeness of my heritage and the worlds I straddled, I was from everywhere and nowhere at once, a combination of ill-fitting parts, like a platypus or some imaginary beast, confined to a fragile habitat, unsure of where I belonged.”

Or this one, which follows a passage about campaigning in Chicago neighborhoods endlessly varied in their class and ethnic makeup: 

“My stump speech became less a series of positions and more a chronicle of these disparate voices, a chorus of Americans from every corner of the state….I’d drive on to the next town, knowing that the story I was telling was true; convinced that this campaign was no longer about me and that I had become a mere conduit through which people might recognize the value of their own stories, their own worth, and share them with one another.”

(This, he said, “worried me” because “the continuing elevation of me as a symbol ran contrary to my organizer’s instincts.” But he acknowledges that it was an “image that my campaign and I had helped to construct,” having deliberately encouraged people to make his candidacy “a vessel for a million different dreams” and himself an epoch-defining symbol of all hope and all change.) 

Again and again, Obama describes important events and incidents in the same fashion, each one a pluralist cornucopia bursting with people from every conceivable background, orientation, and walk of life (with even the zany cosplayers of the world somehow managing to earn their due). Just ahead of 2008’s crucial Iowa caucuses, he recalls: 

“People streamed into the main building from every direction, a noisy festival of humanity. No age, race, class, or body type appeared unrepresented. There was even one ancient-looking character dressed as Gandalf from The Lord of the Rings, complete with a long white cloak, a pluming white beard, and a sturdy wooden staff…” 

A regular variation involves the author offering up what seem to be opposing ideas or concepts only to flatten out their differences to the point that they might as well not exist. His foreign policy team, for example, is initially described as a contrasting blend of those who favored hard power and “more liberal members” inclined towards soft power and multilateralism. This relatively straightforward dichotomy, however, is qualified by the caveat that all members “considered themselves internationalists to one degree or another,” who “believed that American leadership [is] necessary to keep the world moving in a better direction” and that American influence comes “in many forms.” The difference between these apparently juxtaposed geopolitical outlooks is then ironed out still further as Obama informs us that: 

“Even the more liberal members of my team…had no qualms about the use of ‘hard power’ to go after terrorists and were scornful of leftist critics who made a living blaming the United States for every problem around the globe. Meanwhile, the most hawkish members of my team understood the importance of public diplomacy and considered the exercise of so-called soft power, like foreign aid and student exchange programs, to be essential ingredients in an effective U.S. foreign policy.”

When it came to making foreign policy decisions, Obama says, “the question” simply had to do with “emphasis” and the divide, insofar as one existed, was partly generational—older members of the team favoring more conventional foreign policy thinking and younger members, “seared by both the horrors of 9/11 and the images of Iraqi prisoners abused by U.S. military personnel at Abu Ghraib,” being less inclined towards “the Washington playbook.” Any remaining conceptual friction is then smoothed out even more by the author’s assurance that “none of the younger staffers” (“no less patriotic than their bosses”) “were firebrands,” and that they “respected the institutional knowledge of those with deep foreign policy experience.” 

All told, the passage is emblematic of Obama’s remarkable capacity to evoke tremendous nuance and complexity while saying very little, any apparent difference or conflict between the ideas he’s discussing smoothed over by way of elegant rhetorical synthesis. (Thus in this case, for those following along, we ultimately get a foreign policy team whose members are sorted into binarily opposing camps: young/old, hard/soft, unilateral/multilateral—with these distinctions being collapsed under the vague umbrella of “internationalism,” then modified by the caveat that proponents of soft power also believed in hard power and vice versa. This formulation is then further qualified by the proviso that younger members who wanted to break from the staid orthodoxies of the Washington playbook nonetheless held the foreign policy establishment they ostensibly disliked in high esteem.)

Predictably enough, the author’s own political identity is rendered in much the same way: as a finely-balanced synthesis of contrasting traditions, beliefs, temperaments, and impulses—at once progressive and pragmatic, idealist and realist, grand in vision but keenly aware of norms and political constraints, attuned to injustice but moderate in word and deed; a harmonious union of various constituent identities and ideological hues as infinitely varied as the wards that make up Chicago’s 13th State Senate district or the flowers in the White House Rose Garden; as infinitely varied as America itself. Reflecting on his first 100 days in office, for example, Obama calls himself “a reformer, conservative in temperament if not in vision.” Reformism and conservatism may appear to be opposites, but no matter—in Obama they are unified and the contradiction is dissolved. Study enough of Obama’s words and speeches, in fact, and they all begin to read as transliterations of his most memorable flourish, “hard and soft power” in Chapter 13 of A Promised Land serving a roughly equivalent function to “red states and blue states” in 2004’s DNC keynote address:

“E pluribus unum. Out of many, one…there is not a liberal America and a conservative America—there is the United States of America. There is not a Black America and a White America and Latino America and Asian America—there’s the United States of America. The pundits, the pundits like to slice-and-dice our country into Red States and Blue States; Red States for Republicans, Blue States for Democrats. But I’ve got news for them, too. We worship an awesome God in the Blue States, and we don’t like federal agents poking around in our libraries in the Red States. We coach Little League in the Blue States and yes, we’ve got some gay friends in the Red States. There are patriots who opposed the war in Iraq and there are patriots who supported the war in Iraq…”

From his debut book Dreams From My Father to the present day, Obama’s tendency to invoke grand, dialectical oppositions then resolve them with abstract appeals to unity or similitude has been a hallmark of his style. Combined with his flair for lofty, even mythical imagery and ability to fuse his thoughts and biography with everything around him, the upshot is a rendering of events in which every strand of history, culture, and ideology appears to realize itself in Barack Obama: a man whose life and presidency represent the synthesis of every strain of American life hitherto in tension. The same basic pattern recurs again and again throughout Obama’s prose and speeches in great Enigma Variations of rhetorical triangulation—as everything from his music preferences to his foreign policy team find the old dichotomies dismantled and an underlying harmony revealed. At times this rhetoric has even sounded like Biblical prophecy, as when Obama expressed his confidence that future generations would “look back and tell our children that… this was the moment when the rise of the oceans began to slow and our planet began to heal” (upon being elected, Obama immediately appointed BP’s climate change-denying chief scientist to his Department of Energy). If that sounds like hyperbole, consider how some of Obama’s smartest and most enthusiastic supporters responded to his words. A 24-year-old Ezra Klein wrote in January of 2008 that: 

“Obama’s finest speeches do not excite. They do not inform. They don’t even really inspire. They elevate. They enmesh you in a grander moment, as if history has stopped flowing passively by, and, just for an instant, contracted around you, made you aware of its presence, and your role in it. He is not the Word made flesh, but the triumph of word over flesh, over color, over despair. The other great leaders I’ve heard guide us towards a better politics, but Obama is, at his best, able to call us back to our highest selves, to the place where America exists as a glittering ideal, and where we, its honored inhabitants, seem capable of achieving it, and thus of sharing in its meaning and transcendence.” [emphases Klein’s]

Obama emphatically insists he was uncomfortable with those who expressed outsized hopes in him and discussed him in messianic terms, but admits that his campaign deliberately “helped to construct” this association in the public’s mind between the election of Barack Obama to the presidency and the fulfillment of America’s promise and the end to people’s troubles. The route to the “promised land” was through his presidency. It was hope itself, change itself. Elect me, he said, and we will end our divisions, part the seas, and move to a new stage of history. Say what you will, but this is a powerful piece of personal branding. Not for nothing did Advertising Age give Obama its 2008 Marketer of the Year award, the 44th president winning out over Apple and Zappos.

Yes We Can…what? 

Try as he might, Obama’s elegant obfuscations and literary digressions can only take him so far. A Promised Land is, after all, a response to critics and a memoir concerned with recounting the specifics of political decisions from the point of view of the man at their center—an effort which inevitably necessitates the occasional clearly-stated opinion. Even here, however, the author frequently proves difficult to pin down—his narration often ventriloquizing the perspectives of others and invariably placing him somewhere, dispassionately, in between. One again recalls Taibbi in 2007 describing Obama’s capacity to exude a “seemingly impenetrable air of Harvard-crafted moral neutrality” while expending tremendous rhetorical energy “showing that he recognizes the validity of all points of view [and emphasizing] that when he does take hard positions on issues, he often does so reluctantly.” 

For all his talk of grand aspirations and hopes, then, Obama does not come across as someone with a very strong or clearly-defined set of political goals. It is striking, in fact, given the book’s subject matter and length, how little he says about why he wanted to hold elected office in the first place, what he does offer in this regard mostly taking the form of empty platitudes. He suggests, for example, that he could “excite voters in ways” that other candidates couldn’t, that he could use “a different language” than they did, that he could “shake up Washington,” and “give hope to those in need.” As he considers running for president, Michelle asks why he feels that he of all people should hold high office. Obama hesitates, and slips into a reverie about marriage. Snapping back to reality, he then tosses out a few more possible explanations, most of them trite to the point of meaninglessness: he could “spark a new kind of politics,” “get a new generation to participate,” and “bridge the divisions in the country.” As a final answer, he settles on the fact that young Black children would be deeply inspired by his presence in the White House. (This is tangible, true, and shouldn’t be trivialized. But it’s also not a legislative agenda.) 

“For all his talk of grand aspirations and hopes, Obama does not come across as someone with a very strong or clearly-defined set of political goals. It is striking how little he says about why he wanted to hold elected office in the first place…“

Again and again, Obama appears reluctant to define himself by any particular political ideology. The author says he wanted to “avoid doctrinaire thinking,” instead “plac[ing] a premium on what worked” and “listen[ing] respectfully to what the other side had to say.” As examples of his willingness to buck the conventional Washington wisdom, he cites his decision to chastise teachers’ unions over their lack of “accountability” and his willingness to advocate violating Pakistani sovereignty in the pursuit of Osama bin Laden, which even Republicans were unwilling to publicly endorse. Examples of bipartisan cooperation actually yielding anything valuable, meanwhile prove notably sparse, with Obama citing a collaboration in the Illinois Senate with arch-conservative Tom Coburn “on measures to increase transparency and reduce waste in government contracting.”

Though he often presents self-effacingly someone who is overly “professorial” and excessively detail-oriented in matters of policy, this portrayal is the opposite of the truth. Throughout his political career (as in A Promised Land) Obama tended to deal in uplifting abstractions rather than concrete promises or objectives, even of the wonky kind. He relates, for example, an incident from 2007 at an Service Employees International Union (SEIU) forum on healthcare, where Hillary Clinton and John Edwards presented their plans for healthcare reform. When Obama’s turn came, he appeared empty-handed, with no actual vision for how healthcare should work. The then-candidate was roundly criticized, with NBC asking “is Obama all style and little substance?” and noting that he had “provided few details about how he would lead the country.” Ezra Klein remarked at the time that while coverage of Obama had focused on “the Illinois senator’s explosive charisma, preternatural ease on the stump, and inspirational back story,” at the forum he had appeared “unprepared and overwhelmed” when asked by a 23-year-old questioner the very simple question of what he actually intended to do to fix healthcare. In the end, Obama spent much of the 2008 primary arguing against the “individual mandate” that would later become a core part of the Affordable Care Act. 

One cannot help but feel Taibbi had it right when he noted in ‘08 that “you can’t run against [Obama] on the issues because you can’t even find him on the ideological spectrum.” Every time Obama appears as if he is about to take a stand, he qualifies it. This is even true of his 2002 speech against the invasion of Iraq, which the author quotes from in A Promised Land. The speech is largely remembered as an act of some political courage, given how many Democrats ultimately backed the war. In fact, even that speech began with the words: “although this has been billed as an anti-war rally, I stand before you as someone who is not opposed to war in all circumstances,” and reiterated his support for “this administration’s pledge to hunt down and root out those who would slaughter innocents in the name of intolerance.” Similarly, Obama’s 2009 Nobel Peace Prize address is ostensibly a meditation on deep moral questions about peace and violence, but triangulates in similar fashion—its thesis essentially being that while peace is good, sometimes violence is necessary in order to maintain peace. When one revisits Obama’s words and speeches today, it is striking just how unmemorable and lacking in content they really were, beyond vague platitudes so inoffensive it was impossible to disagree with them. 

“Though he often presents himself as excessively detail-oriented in matters of policy, this portrayal is the opposite of the truth… Obama tended to deal in uplifting abstractions rather than concrete promises or objectives.”

Taibbi, watching Obama’s rallies during his first campaign for president, observed that his “presentation is deliberately vague on most counts,” his appeal being “a mood thing, not an issue thing” which ultimately stemmed from his personal qualities: “his expansive eloquence, his remarkable biography, his commanding physical presence.” Taibbi grudgingly found himself rather enchanted by Obama, whose audiences “really seem to believe that his election will fundamentally change the way they feel about their country,” with the candidate himself “a dynamic, handsome, virile presence, a stark contrast to the bloated hairy shitbags we usually elect to positions of power in this country.” Political scientist Adolph Reed, Jr. was less enthused, calling Obama a “vacuous opportunist, a good performer with an ear for how to make white liberals like him,” and warning that “Obama’s empty claims to being a candidate of progressive change and to embodying a ‘movement’ that exists only as a brand will dissolve into disillusionment.” (The historical record shows that Reed was right. Upon his election, Obama sent his organizers home; the movement dissolved, and young people who had voted for Obama were soon pouring into the streets in protest.) 

Tellingly, Obama often talks about what winning the presidency would mean rather than what it would do:

“If we won, it would mean… that the America I believed in was possible, that the democracy I believed in was within reach. If we won, it would mean that I wasn’t alone in believing that the world didn’t have to be a cold, unforgiving place, where the strong preyed on the weak and we inevitably fell back into clans and tribes, lashing out against the unknown and huddling against the darkness.”

He elsewhere adds that he wanted to “deliver the goods” and show “that we could transcend the old logic, that we could rally a working majority around a progressive agenda” and address “issues like inequality or lack of educational opportunity.” The enthusiastic aspiration toward nothing in particular could be seen in his campaign slogan, “Yes We Can,” a resonant affirmation of democratic possibility and collective purpose, which nonetheless begged a very obvious followup: Yes We Can what? 

One passage in the book’s opening chapter dramatically underscores the extent to which Obama’s notion of idealism is much more an affection rooted in abstract political storytelling than an orientation towards any particular goal. Recalling the idealistic temperament of his youth, the author tells us he nonetheless clung to the idea of American exceptionalism, getting into protracted arguments “with friends who insisted the American hegemon was the root of oppression worldwide.” To his credit, Obama acknowledges plenty wrong with the American experiment in practice: “The version of American history taught in schools, with slavery glossed over and the slaughter of Native Americans all but omitted…the blundering exercise of military power, the rapaciousness of multinationals” though he ultimately cannot resist ending the paragraph on a note of derision (“…yeah, yeah, I got all that.”). “But the idea of America,” Obama continues, “the promise of America: this I clung to with a stubbornness that surprised even me. ‘We hold these truths to be self-evident, that all men are created equal’—that was my America.” Extremely redolent of this passage is another which appears more than 200 pages later when, reflecting on how the euphoric public mood that surrounded his inauguration quickly darkened amid the ravages of the financial crisis, Obama wonders:  

“Maybe what was needed was a burst of energy, no matter how fleeting—a happy-seeming story about who we were as Americans and who we might be, the kind of high that could provide just enough momentum to get us through the most treacherous part of the journey.”

The Rhetoric and the Record 

Obama is fastidious in making A Promised Land seem like an uncommonly honest and forthright text. All of the details he offers about what it feels like to be president, what the items on his desk looked like and how the White House kitchen operates, are part of an attempt to make the reader see him as concealing nothing. If he just offers a clear enough window into his own subjective thinking and experiences, the author hopes, we will see that he was, if flawed, at least reasonable, and come to share his conviction that even if he wasn’t a perfect president, he did about the best one job one could hope for given the political context in which he landed. 

To this end, sections are periodically devoted to asking (what at least seem to be) probing questions about the merits of particular policies and political decisions, the very first of which appears near the book’s outset:  

“I confess that there have been times during the course of writing this book, as I’ve reflected on my presidency and all that’s happened since, when I’ve had to ask myself whether I was too tempered in speaking the truth as I saw it, too cautious in either word or deed, convinced as I was that by appealing to what Lincoln called the better angels of our nature I stood a greater chance of leading us in the direction of the America we’ve been promised.”

There are many more paragraphs of this kind strewn throughout the book, Obama employing an approach to his own life and career every bit as ambidextrous as his attitude towards the economy or healthcare policy. “Why would I put her through this? Was it just vanity?” he asks himself while recalling his wife’s initial opposition to his presidential ambitions, before continuing:

“…Or perhaps something darker—a raw hunger, a blind ambition wrapped in the gauzy language of service? Or was I still trying to prove myself worthy to a father who had abandoned me, live up to my mother’s starry-eyed expectations of her only son…”

On at least one occasion, Obama’s tone of inquisitiveness even finds him appearing to question the essence of his own appeal and worldview: 

“How useful is it to describe the world as it should be when efforts to achieve that world are bound to fall short? Was Václav Havel correct in suggesting that by raising expectations, I was doomed to disappoint them? Was it possible that abstract principles and high-minded ideals were and always would be nothing more than a pretense, a palliative, a way to beat back despair, but no match for the more primal urges that really moved us, so that no matter what we said or did, history was sure to run along its predetermined course, an endless cycle of fear, hunger and conflict, dominance and weakness?”

Again and again these questions pile up, their tone always pensive, probing, and self-critical. A Promised Land is effective in large part because it feels authentic and true, as if Obama is offering a thoughtful examination of his motives, successes, and failures. The capacity to engage in self-criticism, even of the harshest kind, makes it seem like he is being straight with us and offering up an objective reading of events. Thus when Obama fails to convincingly answer his own questions or begins to distort the truth in ways that seem deliberate, it begins to seem that his authenticity may be a performance, a calculated act rather than genuine soul-bearing. 

Suspicion inevitably ensues when apparently brooding inquiries go unanswered or questions about major decisions come with passive rejoinders like “Whether I was demonstrating wisdom or weakness would be for others to judge.” Eventually we find ourselves starting to wonder whether Obama is just a politician trying to get us to like him, and what initially seemed honest begins to feel manipulative. For instance, Obama says that while he was reluctant to run for president, conversations with Ted Kennedy and Harry Reid (relayed in the form of suspiciously well-remembered monologues) helped convince him to do it. Obama wonders aloud whether he is in politics for the wrong reasons, but his story is told in such a way as to make us convinced he must have been in it for the right reasons. The textual evidence shows that he was a reluctant office-seeker, not a careerist, which is persuasive—until we remember that the textual evidence all comes from Obama himself. 

This becomes even more obvious when we actually analyze the facts of Obama’s presidency and compare the reality of what happened to the story Obama tells about it. It’s important to examine the facts carefully against the story, because Obama spends much of his time defending himself against critics, and those defenses can be convincing when particular facts are left out. After all, Obama strongly intones that he did as well as one could reasonably expect given that he (1) is a mortal, fallible human being rather than a messiah and (2) had to operate within the constraints of a highly dysfunctional political system, opposed by a psychopathic and racist Republican party, undermined by a media with little interest in substance, and having to juggle many competing interests. He is right that those constraints exist. The Senate is real, the political right is racist and obstructionist, and the media does tend to focus on trivialities. It’s also impossible to run a counterfactual to see what the world would have looked like if Obama had made different choices. Given how sympathetic and effective the author’s self-presentation is, readers who only look at the evidence found in A Promised Land may well feel that criticism of him is downright unreasonable. Portraying himself as both a normal person with human failings and a progressively-minded idealist, the reader is left to ask: what different choices could he have made? One can criticize Obama, sure, but what exactly did you want? 

There are, however, many instances in which Obama made clear choices, and it can be demonstrated that those choices were wrong and that the way he presents them is dishonest. Take healthcare, for instance. Obama says that the Affordable Care Act was constructed the way it was because he needed to appease conservative senators. But he also says that he deliberately crafted his healthcare reform in a way that would appeal to Republicans, because he hoped that by securing bipartisan support he might make the bill seem less partisan in a way that would protect it from future attack. This is an admission that concessions were made that probably did not strictly need to be made in order to ensure the bill’s passage in a Democratic congress. Instead, they were made on a theory of political pragmatism, the theory that bipartisan cooperation on healthcare reform is possible. 

This theory turned out to be flat wrong. The ACA’s deliberately conservative design did not keep conservatives from viciously attacking it. Obama intentionally modeled his reform on “Romneycare” and previous plans from the right-wing Heritage Foundation. In fact, it was meant to be a bill that the private insurance industry could love, because it would require every American to purchase their product and would provide generous government subsidies that would go into the companies’ pockets. Obama thought that it was so reasonable, so little of a threat to Republican ideology and interests, that they couldn’t possibly be strongly opposed to it. It followed market principles! It propped up corporations! It did not socialize either insurance or care! But Republicans despised the ACA and tried to convince Americans that Obama was going to have government “death panels” deciding to pull the plug on their grannies. Not a single Republican ended up voting for the final version of the ACA in either the House or the Senate. Republicans, far from accepting Obama’s olive branch, snapped it in half and set it alight. They not only resisted nearly any initiative he proposed: they portrayed a compulsively compromising centrist as a radical bent on destroying the American way of life. 

Obama also downplays the fact that some of the “constraints” he was under were self-imposed, in that they came from his own unwillingness to push the envelope and be bold. He discusses, for instance, the anger of LGBTQ activists over his administration’s refusal to simply unilaterally order an end to Don’t Ask Don’t Tell, but says that he wanted to get the military brass on board, and was worried his Republican defense secretary would resign if pushed too hard on the issue. (God forbid he lose that guy.) Some issues, such as his pro-privatization education “reforms,” or the drone strikes on civilian populations criticized by Human Rights Watch and the ACLU, or mass deportation, are barely touched on in the book, perhaps because they were clear matters of policy choice and thus fit awkwardly with its wider effort to portray Obama as someone whose disappointing compromises were imposed upon him by circumstance. (On targeted killing, Obama does not address the human rights reports but hopes it is enough not to have taken pleasure from his actions and to have condemned his predecessor: “I took no joy in any of this…But the work was necessary, and it was my responsibility to make sure our operations were as effective as possible. Moreover, unlike some on the left, I’d never engaged in wholesale condemnation of the Bush administration’s approach to counterterrorism.”)

Take, as another example, the way Obama repeatedly cites the existence of the Senate filibuster as a reason why conservative Democrats needed to be appeased on healthcare. The case sounds ironclad, until you consider that a simple majority of Senators (which the Democrats had) could have eliminated the filibuster at multiple points. Obama rather amazingly admits this, but says that in 2009 nobody was contemplating changing the process. This is not the case—a 2009 Politico article, for example, argued that “while Democrats rail against the GOP’s use of the filibuster, they seem wary of doing anything about it.” It was not, in fact, impossible to overcome Joe Lieberman’s hostility to a public option: it was simply that the actions this would have required looked radical and violated the sacred norms of institutional Washington. The preservation of these norms is considered by some politicians to be far more important than whatever ultimate ends politics is actually directed toward. (Obama, for example, complains in the book about protesters who called George W. Bush a war criminal on Bush’s last day in office. To Obama, this is simply rude, and rudeness is a vice so unconscionable that it must be avoided at all costs, even the cost of letting a war criminal get away with his war crimes without being yelled at.) 

In fact, Obama made it clear that he had never been a progressive the moment he selected his staff. He had always said that he believed in bipartisanship, and he meant it. In his address at the Democratic National Convention in 2004, which had made his national reputation, Obama had rejected the idea that the United States needed to be “divided,” suggesting that “Red America” and “Blue America” needed to sit down in a room together and understand each other. To that end, when he became president, Obama gave Republicans concessions that nobody on his side was actually asking him to give. In A Promised Land, he says that to show he was serious about believing that Republicans deserved to govern, he asked George W. Bush’s defense secretary, Robert Gates, to stay on, even though Gates “was a Republican, a Cold War hawk, a card-carrying member of the national security establishment, a prior champion of foreign interventions I had likely protested while in college, and now defense secretary to a president whose war policies I abhorred” and “had helped oversee the arming of the Afghan mujahideen.” Another way of putting that is that Gates had a demonstrated record of incompetence and poor judgment, but Obama felt that keeping a discredited, right wing figure from the administration whose record he’d ostensibly run against in a powerful position would show him to be “serious” and “nonpartisan.” 

This was not the only such effort Obama made. He tried to appoint Bush’s lead TARP negotiator, Judd Gregg, to be his Commerce Secretary (Gregg declined). He admits he gave legislative concessions to Republican House whip (and later Majority Leader) Eric Cantor not because he received anything in return, but as a gesture of good faith. Obama launched a bipartisan commission on deficit reduction (deficits being a particular hobbyhorse of his) that, predictably, proposed cutting Social Security and raising the retirement age to 69 (less than 10 years before the average person is expected to croak).  

Not only did Obama reach out to Republicans like Gates and Gregg, but he begged Rahm Emanuel to be his chief of staff. Emanuel was reluctant, but the president-elect insisted that he wanted no one else. Obama acknowledges that some people might find his choice insane: “Didn’t he represent the same old triangulating, Davos-attending, Wall Street-coddling, Washington-focused, obsessively centrist version of the Democratic Party we had been running against? How can you trust him?” Though Obama asks the right questions, he very tellingly does not actually answer them, saying instead that “these were all variations on a question that would recur in the coming months. What kind of president did I intend to be?” (Rahm Emanuel would go on to cover up the murder of a young Black man at the hands of police.) 

Obama similarly pleaded with Hillary Clinton to accept the position of secretary of state, despite her well-known hawkishness and vote for the Iraq war (just as he had chosen Joe Biden, one of the Bush administration’s most zealous advocates in the Senate during the run-up to the invasion and its early months, as his running mate). Though Obama cites his desire to “unify a still-divided Democratic Party,” concerns that Clinton might “second-guess” him “from her seat in the Senate,” and a desire to “self-consciously mimi[c] Lincoln by placing a former political opponent in my cabinet,” his ultimate reason for picking Clinton is pitched in the bland language of H.R.: “I thought Hillary was the best person for the job,” he writes, citing her “intelligence, preparation, and work ethic.”

This is also more or less the justification he gives for bringing Larry Summers and Tim Geithner into his administration, despite the pair’s well-known chumminess with Wall Street. Obama admits that the two men were tied to the Clintonian neoliberalism that characterized Washington “politics as usual” but says he had no choice but to pick seasoned Beltway veterans to mop up the mess of the financial crisis. This decision turned out to have serious consequences: Geithner notoriously defied Obama’s order to draw up a plan for bank nationalization, and both Geithner and Summers objected to conditioning aid to banks on restricting the amount that could be paid in executive bonuses, saying this would constitute an unacceptable interference with the freedom of contract and cause “irreparable damage to our market-based system.”

The parts of A Promised Land about the response to the financial crisis are where the book begins to seem not just like a rationalization for mushy centrism, but a deeply dishonest rewriting of history. Ryan Cooper, in his review for the Week, notes that Obama simply leaves out inconvenient information. For instance, there were plenty of ideas floating around for how Obama could create a stimulus that would be large enough to fill the hole in the economy, but “Obama’s team dismissed all of these ideas out of hand,” proposing a stimulus they knew from the outset would be insufficient and not even trying to get something adequate. Cooper quotes Obama economic adviser Austan Goolsbee, who admitted that the administration could have forced banks to give homeowners more mortgage relief, or gotten restrictions on executive compensation, but had no interest in fighting for these kinds of concessions. 

Obama must know that if he told the truth about what happened, he would not come across looking very good, because he spins stories so that readers will not grasp the critics’ arguments. Here, for instance, is how Obama explains his administration’s failure to provide more relief to homeowners who were facing foreclosure:

“Affordable-housing advocates and some progressives in Congress were pushing a large-scale government program to not only reduce monthly mortgage payments for people at risk of losing their homes but actually forgive a portion of their outstanding balance. At first glance the idea had obvious appeal: a ‘bailout for Main Street, not Wall Street,’ as proponents suggested. But the sheer scale of lost home equity across the country made such a principal-reduction program cost-prohibitive. Our team calculated that even something the size of a second TARP—a political impossibility—would have a limited effect when spread across the $20 trillion U.S. real estate market.” 

This is nonsense, though it might easily read like cool-headed practical thinking. Why would the government need to spend money in order to make banks reduce the principal on people’s mortgages? The government could just require banks to reduce principal. Obama is suggesting that there was no choice but to have the government compensate the banks for principal reductions, and that such compensation would be cost prohibitive. But there’s no reason the government needed to compensate the banks; they should have taken the loss, because it was their recklessness that caused the crisis. What Obama deems impractical was only impractical under self-imposed constraints.

“When Obama fails to convincingly answer his own questions or begins to distort the truth in ways that seem deliberate, it begins to seem that his authenticity may be a performance, a calculated act rather than genuine soul-bearing.” 

Likewise, Obama repeatedly says that the American public was crying out for what he calls “Old Testament justice” against Wall Street, because of their “understandable desire to see those who’d done wrong punished and shamed,” demanding that the bankers responsible for the economic collapse face criminal prosecution. Obama explains away his administration’s decision not to prosecute by saying that the law simply didn’t permit it, and that he didn’t wish to “stretch the definition of criminal statutes.” In fact, as Jesse Eisinger documented extensively in his book The Chickenshit Club: Why the Justice Department Fails to Prosecute Executives, prosecutors could well have gone after bank executives but were simply too, well, chickenshit. Jed Rakoff, one of the more sensible members of the federal judiciary, discusses the failure in his useful forthcoming book Why the Innocent Plead Guilty and the Guilty Go Free. Rakoff writes that there was ample evidence of mass fraud—the “sow’s ear” of dodgy mortgages could not have been turned into the “silk purse” of AAA-rated bonds unless someone was declining to tell the truth. It was not the law that was the problem; a better understanding of the reasoning comes from Obama’s telling admission that it would have “required a violence to the social order, a wrenching of political and economic norms” to put bankers in jail—after all, it simply isn’t done in Washington, and Obama may have ended up having to put some of his own donors behind bars. Furthermore, his own Attorney General Eric Holder explicitly admitted—though you won’t find it in the book—that prosecutions sometimes weren’t brought because of the economic effect that such prosecutions would have:

“I am concerned that the size of some of these institutions becomes so large that it does become difficult for us to prosecute them when we are hit with indications that if you do prosecute, if you do bring a criminal charge, it will have a negative impact on the national economy, perhaps even the world economy.” 

The administration declined to charge HSBC with money-laundering, for instance, because it feared that there would be negative economic consequences. What was lacking was not evidence of criminality but the willingness to do something perceived as “radical,” i.e., to enforce the law consistently against both rich and poor. Obama laments at one point that the “laws as written deemed epic recklessness and dishonesty in the boardroom or on the trading floor less blameworthy than the actions of a teenage shoplifter.” But that’s a lie. The laws as written criminalize fraud equally no matter who you are. The laws as applied by Obama’s prosecutors treat the two cases differently because, as Holder indicates, prosecuting teens doesn’t hurt the economy. What this amounts to is making some banks “too big to jail,” meaning that they can commit crimes with impunity because prosecuting them is considered bad for the economy. This makes a mockery of “the rule of law,” of course, because it means that the richer you are the more crimes you are allowed to commit, because of your role in the economy. 

The misrepresentations pile up throughout A Promised Land. Obama leaves out a number of facts that might prove embarrassing or be difficult to explain away as well-meaning failures. For instance, Bernie Sanders goes unmentioned in the book, which may well be because Obama’s main interactions with Sanders came during the Vermont senator’s clashes with the administration over its attempts to cut Social Security and the U.S. Postal Service. In Obama’s telling of the Copenhagen climate summit, he burst in to save talks that were going nowhere, pressuring intransigent countries like China and India to agree to crucial emissions reductions. In fact, the United States is widely blamed for being the reason that the Copenhagen talks produced no binding commitments, and instead resulted in a completely toothless aspirational pledge. 

The Limits of Empathy 

Early in the book, Obama says he has deliberately attempted to give the reader a vivid first-person description of what it feels like to be the president, what it’s like to walk down the West Colonnade past the Rose Garden each morning on the commute from the residence to the office, what it’s like to find yourself being saluted, give a soaring speech to a huge crowd, what it’s like to feel the weight of people’s expectations and know that your decisions have life or death consequences, what it’s like to accidentally fumble your words and then see your “gaffe” earn a four-day news cycle. A recurring theme of the memoir is “putting oneself in others’ shoes”—Obama is constantly putting himself in the shoes of the uninsured, of foreign leaders, even of Somali pirates—and he, in turn, puts the reader in his shoes.

One of Obama’s core convictions is that a lack of empathy is one of the root problems in politics. If we just learned to imagine ourselves in each other’s places—if the Israelis could understand the Palestinians and vice versa, if Republicans could understand Democrats and vice versa—we would learn that each of us, deep down, wants roughly the same things, and we could figure out compromises that would prevent division and hostility. In A Promised Land, as in his political career, Obama wants to be a bridge between antagonistic interests and groups: his centrism granting that Republicans are right about some things and Democrats right about others; his multiracial identity allowing him to be proudly Black while seeing where white people, even racist ones, are coming from (his famous “race speech” tries to sympathetically contextualize his own grandmother’s bigotry). 

But the more one scrutinizes A Promised Land, the more one feels manipulated. Obama powerfully performs empathy and modesty and conviction, but when one steps back and asks “Empathy for whom?” or “Conviction about what?” the whole thing begins to look shallow. His empathy is also selective. He speaks about understanding all points of view, but then is weirdly soft on George W. Bush, whom he likes on an interpersonal level. (And he cites George H.W. Bush as an example of a president whose foreign policy he finds admirable.) He condemns “the arrogance of men like Dick Cheney and Donald Rumsfeld” in starting the Iraq war, but strangely leaves Bush himself off. Those protesters committed an unseemly violation of the norms of civility and decorum by going after Bush. But, one might ask, what about the hundreds of thousands of people who died violent deaths because of George Bush’s criminality and lies? Why would Obama be more concerned for Bush’s feelings than about justice? Does Obama disagree with the protesters’ case that Bush committed war crimes? If not, why does he believe that politeness should mean we decline to mention a powerful person’s unprosecuted atrocities? 

In fact, Obama is ultimately nicer to George W. Bush than he is to Jeremiah Wright, the pastor whose fiery political sermons caused a P.R. problem on the 2008 campaign trail (and whose services Obama attended for years). After first trying to contextualize Wright in a widely-praised speech on race, Obama subsequently disavowed and broke ties with him completely. What Obama never did, and still does not do, is explain that the sermons for which Rev. Wright was criticized were wholly stripped of their context. Clips circulated repeatedly of Wright shouting “God damn America,” and Obama repeats the snippet without reproducing the passage from which it is drawn:

“And the United States of America government, when it came to treating her citizens of Indian descent fairly, she failed. She put them on reservations. When it came to treating her citizens of Japanese descent fairly, she failed. She put them in internment prison camps. When it came to treating her citizens of African descent fairly, America failed. She put them in chains, the government put them on slave quarters, put them on auction blocks, put them in cotton fields, put them in inferior schools, put them in substandard housing, put them in scientific experiments, put them in the lowest paying jobs, put them outside the equal protection of the law, kept them out of their racist bastions of higher education and locked them into positions of hopelessness and helplessness. The government gives them the drugs, builds bigger prisons, passes a three-strike law and then wants us to sing “God Bless America.” No, no, no, not God Bless America. God damn America—that’s in the Bible—for killing innocent people. God damn America, for treating our citizens as less than human. God damn America, as long as she tries to act like she is God, and she is supreme. The United States government has failed the vast majority of her citizens of African descent.”

Wright was arguing that those who commit sin receive damnation, and that America believes it deserves to be blessed without reckoning with its sins. It is an important and defensible point. In fact, it is almost an inarguable point, and the only way you can get around the fact that 90 percent of Wright’s indictment is true beyond a reasonable doubt is to air only three seconds of it, which is what the news media did.

“Obama is ultimately nicer to George W. Bush than he is to Jeremiah Wright…”

Obama is now out of office, and there is nothing to stop him from giving Wright’s side of the story forcefully and honestly. Instead, he says that he felt the reverend’s sermons were inappropriate, in part because Wright used to discuss racism and militarism in front of a “prosperous” congregation. 

“There were times when I found Reverend Wright’s sermons a little over the top. In the middle of a scholarly explication of the Book of Matthew or Luke, he might insert a scathing critique of America’s drug war, American militarism, capitalist greed, or the intractability of American racism, rants were usually grounded in fact but bereft of context. Often, they sounded dated, as if he were channeling a college teach-in from 1968 rather than leading a prosperous congregation that included police commanders, celebrities, wealthy businesspeople, and the Chicago school superintendent.”

God forbid police commanders or the school superintendent should have to hear “a scathing critique of America’s drug war”! (Obama’s treatment of Wright is especially galling when one considers that it was Wright who inspired Obama’s “audacity of hope” phrase. Obama lifted the words but left out Wright’s meaning, for which he has obvious contempt.)

One can acknowledge that the Wright affair put Obama in a genuine bind: stick by his reverend and risk being destroyed in the press, or throw him under the bus and achieve an important landmark for Black Americans by becoming president. Any critical account of Obama needs to acknowledge the fact that he was under a unique set of constraints. The racism directed toward him was extreme. For Fox News, a fist bump became a “terrorist fist jab.” The right treated him as if he were Malcolm X for noting that if he had had a son, that son would be Black. When Obama correctly pointed out that the Cambridge police department had acted “stupidly” in arresting Harvard professor Henry Louis Gates for breaking into his own home, Obama was immediately faced with demands to apologize, and felt the need to backpedal by inviting Gates and the arresting officer to the White House for a “beer summit.” And then there was birtherism, the disgusting, transparently racist conspiracy theory that helped to propel the current president to his position of political prominence.

It is the case, then, that Obama may not have had as much room to maneuver simply by virtue of the fact that in a racist country, he was under an impossible level of scrutiny. But this doesn’t explain why after leaving office, when he is free to speak his mind, Obama appears to partly blame Gates for his own arrest. It does not explain why he declines the opportunity to fully expose the racist attacks on Wright for what they were. As we have written before, Obama’s post-presidency can resolve definitively the question of who he really is and what he wants, because the constraints that were on him as a president have been removed. When Obama looks back proudly, then, on having stood up to the teachers’ unions, appointing a neocon to head his defense department, or not intervening forcefully to protect people during the financial crisis because he held the sanctity of the market to be an inviolable shibboleth, we can be fairly certain he is honestly communicating his real beliefs.

From its outset to its conclusion, A Promised Land makes clear that Obama sees himself like one of the workmen in Norman Rockwell’s “Working on the Statue of Liberty”—the guardian of a good and solemn order. But he also makes clear what kind of order he seeks to protect, as when he explicitly says that prosecuting bankers or taking more aggressive measures during the financial crisis would have done violence to the social order. This is perhaps the most telling sentence in the whole book, because it makes so explicit where (and on whose side) Obama ultimately stands. Unless we believe that the criminal laws should simply not apply to the rich, it would be outrageous not to prosecute those who dressed up bad mortgages as good ones. For Obama, aggressive government intervention during a national economic catastrophe constitutes unthinkable “violence to the social order.” The single greatest liquidation of middle class wealth since the Great Depression—a direct result of the economic failures that produced the crisis and the administration’s subsequent refusal to intervene—apparently does not. 

The social order Obama commits himself to protecting, in other words, is the status quo. Reverend Wright’s sermons, by making bourgeois parishioners uncomfortable, ultimately threatened that status quo. The protesters calling Bush a war criminal threatened it, too. Providing massive mortgage relief would have threatened it. Nationalizing the banks would have threatened it. Scrapping the filibuster would have threatened it. Obama is congenitally incapable of doing or saying anything he thinks will rock the boat too much or appear “unreasonable.” Thus even now, though he must surely know better, Obama says that it “doesn’t make sense” for Joe Biden to assume that Republicans “are going to try to obstruct, stonewall, lie, and do everything they can to defeat my proposals” and perhaps instead will “consider it in their interest at least early on to cooperate.” His presidency provides eight years of evidence that Republicans do not consider it in their interest to cooperate, and that they are probably right about that. But if Obama were to admit that Republicans do not have an incentive to cooperate, and that Democratic naivete about this is politically suicidal, his entire kumbaya posture about the “bridging of divides” would become impossible to maintain. 

Barack Obama is not stupid. He understands the world better than any previous American president. As a Black man, he has seen too much to accept the country’s most galling lies about itself. In a recent interview, Obama was relatively honest about the Democratic Party’s lurch to the right, pointing out the effect of “free market ideology” on “unraveling the social compact.” But Obama is, as always, the prisoner of etiquette and norms. He knows what the Iraq war was, but cannot call his predecessor a criminal. He knew the CIA tortured people, but would not prosecute its malefactors. He knew the financial crisis would destroy millions of livelihoods and make the rich even richer, but rejected popular demands for activist government. Being the kind of president some progressives hoped and believed he would be would have required him to militate against an order he committed to defend decades ago. It also would have required the abandonment of his “everything to everyone” aspiration and necessitated the discarding of his own carefully-crafted universalist identity. 

In political life, interests inevitably diverge and cannot be harmonized. The short-term financial interests of fossil fuel companies are in tension with the long-term survival interests of human civilization. You cannot make a playlist for everybody. You have to make choices, and those choices will express value judgments. Do you stand with the oil company polluting the town’s water supply or with its residents? Do you stand with the workers striking for better wages or with the CEO? Will you maintain Bush’s foreign policy or will you reject it? Are you with Rahm, Larry, and Hillary, or with average Americans at risk of losing their homes? Health insurance companies or sick people whose premiums prevent them from seeing a doctor? Which side are you on? Obama still insists he is with everyone, that his team is America. But there is no such thing as not taking sides. 

Obama’s failures and blind spots, of course, were not ultimately borne of good faith errors or misunderstanding—but of something much worse. He was not just naive about human conflicts of interest. By picking a side, but pretending there were no sides, Obama mobilized the hopes and idealism of millions only to betray them. He encouraged people to see his candidacy as the embodiment of their own aspirations for a better future and, having stuffed his cabinet with Beltway veterans who were never going to deliver, now insists that anyone who objects simply does not share in his deep understanding of political reality. He gave “idealism” a bad name by intoning that ideals and platitudes are the same thing, and “pragmatism” a bad rap by suggesting that being unwilling to fight is the same as being conscious of one’s limitations. If a generation of angry young people are now becoming socialists, it is in part because Obama’s hypocrisy and vacuity have radicalized them. We can and should appreciate Obama’s achievement in breaking a civil rights barrier by becoming the first Black president. But the main lesson to take from A Promised Land is that Obama’s politics did not, and cannot, provide a viable blueprint for the future. The “good and solemn order” of which he sees himself the “guardian” must be defeated rather than defended. The road to the “promised land” lies beyond the fraudulent universalism of Barack Obama. 

* You can almost see it now: “That garden sure was a pretty sight, full of flowers of every kind that changed color with the seasons: roses, lilies, daisies, chrysanthemums, with petals of every hue. Each time I passed it, I would reflect on the infinite diversity and brightness that make the American experiment the greatest in the world…”