We read Obama’s memoir so you don’t have to. But it’s a historic page-turner.

A hefty new presidential memoir hits stores this week. Given that neither his predecessor nor successor are renowned as writers, you’d probably guess the author was Barack Obama even if you hadn’t seen the news his book generated. (In brief: Obama kept smoking cigarettes even in the White House, only quitting when the ACA passed; he’s troubled by his legacy in the Middle East; he unloads on people like Mitch McConnell in a way we’ve never seen from the supremely anger-managed president.) 

When stripped of its headlines, though, how does A Promised Land stack up as a page-turner? After all, there are plenty of pages to turn: 700, not counting the acknowledgements and index. Obama’s first book, Dreams From My Father (1995), was a profoundly good read from an unfiltered young man with a heck of a family tale to untangle; his 2006 follow-up, The Audacity of Hope, was more guarded (he was then a U.S. senator mulling a presidential run), more political, more skippable.

The good news is that Promised Land is about 80 percent Dreams to 20 percent Audacity. The filter is off again; liberated by the knowledge that it wouldn’t be published until after the 2020 election, Obama is able to literally call bullshit when he saw it (a word he employs liberally). Even though this first volume of his memoirs barely even covers his first term, ending with the killing of Osama Bin Laden in 2011, that doesn’t stop Obama unloading on Trump for his racist birther nonsense, or tracing the roots of today’s GOP to the dark forces unleashed by Sarah Palin in 2008 and the Tea Party in 2009. 

It does suffer at times from excessive digressions; ever the professor, Obama wants to make sure we’ve got a thorough background in every domestic and international conflict. But as an author, he is just inherently talented — at dialogue, pacing, character portraits, even comic timing. The jokey chats he recalls aren’t that funny, but delivery is all. There’s a you-are-there feel to every scene, and his conversations with Michelle — who never quite reconciles herself to life in a fishbowl — seem real and intimate. 

I’ve read a lot of political books in the Trump era, and this was the first I couldn’t speed read. It demands to be savored.

In short, I’ve read a lot of political books in the Trump era, and this was the first I couldn’t speed read. It demands to be savored. Which may have something to do with the fact that Obama still prefers to write with pen and legal pad — “finding that a computer gives even my roughest drafts too smooth a gloss and lends half-baked thoughts the mask of tidiness,” he reveals in the preface. See what I mean? Even his writing advice has a soaring quality to it.

All that said, who has the time to plough through 700 pages in this day and age, especially when the subject matter can still bring on political PTSD? If you can’t bear the journey to the Promised Land, here’s what I learned along the way.   

1. The Land of Might-Have-Been

Personally, whenever I think back on the Obama presidency from 2020, I find my brain sticks in a rut of what-ifs. 

What if he hadn’t spent so much time in those first two years trawling for bipartisan votes from Republicans in Congress who were clearly acting in bad faith? What if the public option hadn’t been dropped from Obamacare? What if he hadn’t abandoned the movement he built in 2008 and had continued mass rallies through 2010, denying the Tea Party at least some of its midterm victory? Or … what if he hadn’t run in 2008, opting to gain more than three years of Senate experience — might America just have reelected Obama to a second term instead of ousting Trump from his first? 

So it was surprising, if not exactly heartening, to learn that Obama is also bedeviled by woulda coulda shouldas. The book is filled with them, and he’s not shy about sharing. “I’ve had to ask myself whether I was too tempered in speaking the truth as I saw it,” he writes on the third page. (This was one of a handful of moments where I found myself yelling at the book like Luther the anger management translator: Oh, ya think?) 

Obama recalls his walks to work in the West Wing and is filled with “a desire to turn back the clock and begin again.” Recapping his career pre-2008, he “can’t help but wonder” what would have happened if he’d stayed a community organizer. His biggest 2008 campaign gaffe, the one about “bitter” voters who “cling to guns or religion,” still tortures him: “Even today I want to take that sentence back and make a few simple edits.”

But one of the qualities of the book is that it helps us all, Obama included, get over the what-ifs and deal with the world as it was. (This kind of collective therapy has a word: history.) Calmly and effectively, he marshals the facts to remind us of the almost impossible pressures he faced. Few presidents have risked such catastrophic consequences from making the wrong choice. 

Looking at his first two months in office, when the global financial system was on the brink of collapse, the president finds himself “in many ways” agreeing with “thoughtful critics” who lament that Wall Street didn’t learn its lesson when it was bailed out by TARP. Maybe he should have seized the opportunity to break up big banks “and sent white-collar culprits to jail”:

I wonder whether I should have been bolder in those early months, willing to exact more economic pain in the short term in pursuit of a permanently altered and more just economic order. The thought nags at me. And yet even if it were possible for me to go back in time and get a do-over, I can’t say that I would make different choices… worst-case scenario, we might have tipped into a full-scale depression.

2. The walking contradiction, defined

You can’t understand Obama until you understand that even Obama can’t really understand Obama. He is, he constantly admits, a contradiction: Hawaiian and Chicagoan, with smatterings of Kansas and Indonesia. Culturally, Black and white. Effortlessly gregarious in public with a strong need to work alone at night. The president who took us out of Iraq and deeper into Afghanistan. A booster of government who cut taxes more than Reagan. A  socialist to some, maddeningly moderate to others. 

You can’t understand Obama until you understand that even Obama can’t really understand Obama.

But in the paragraph after deciding he wouldn’t want a do-over of those fraught early months of 2009, Obama offers the most succinct description of his political personality I’ve seen — one with which his supporters and detractors would be hard-pressed to argue. Rather than having a “revolutionary soul,” he says, “I was a reformer, conservative in temperament if not vision.” 

No sentence could better sum up the achievements and the coulda-been achievements of the Obama years. He was responsible for reforms, had grand visions, inspired (and still inspires) millions of hopes, but that conservative temperament prevented nearly all the change from getting close to revolutionary. Circumstances conspired in the same direction. “I didn’t like the deal,” he writes of the need to deploy more troops to Afghanistan in 2009. “But in what was becoming a pattern, the alternatives were worse.”  

3. The ambiguity… 

The paralyzing ambiguity of a political genius who can see all sides is evident throughout the book. “If every argument had two sides, I usually came up with four,” Obama writes (he’s nothing if not self-aware). And nowhere is this more evident than in his ambiguity about running for president so young in the first place. 

Sure, he admits, he had the ego and the instinct for the job. Everyone around him was telling him he’d tapped into something historic, including Majority Leader Harry Reid, who told him in 2006 that languishing in the Senate for another decade wouldn’t make him a better president. “They’d divined what was best in me,” he says of the voters of 2008, “the voice insisting that for all our differences, we remained bound as one people.”

At the same time, Obama became increasingly concerned throughout that surreal year about the pedestal his supporters had put him on: Being human, he was sure to disappoint them eventually. As early as 2006, before even announcing, he has a liminal dream of stepping into a portal severed from the world, and hears a voice (common in liminal dreams) saying “no, no, no” — which shakes him out of bed and into a soothing glass of vodka. 

His deepest fear, he writes, “was no longer of irrelevance, or being stuck in the Senate, or even losing a presidential race. The fear came from the realization that I could win.”   

4. … and the certainty

Obama wouldn’t be a contradiction if he wasn’t certain as often as he is ambiguous. He may deliberate a lot, but once he makes a decision, he invariably sticks with it. This seems to extend to a kind of Cassandra-like certainty about the future, once he passes a kind of tipping point of knowledge. 

One such moment of clarity comes in October 2008, when his presidential opponent John McCain insists they both sit down at the White House with Congressional leaders and then-President Bush to discuss the rapidly-accelerating financial crisis. But McCain fumbles when asked for solutions. “There are moments in an election battle, as in life, when all possible pathways save one are suddenly closed; when what felt like a wide distribution of probable outcomes narrows to the inevitable.” He knew he’d won the election.

He has these moments of certainty in office, too, on all the big tough decisions. On going ahead with the Bin Laden raid, for example, his staff was extremely divided. Joe Biden believed it was too risky. Hillary Clinton said she was “51-49” in favor. But Obama has been slowly narrowing down the options for weeks, “working the odds, quietly and often late at night” and feels “fully prepared and fully confident” in finally making the go order. 

That’s leadership: the informed variety of instinct, not the chaos-creating pure id we’ve suffered under for the past four years.    

5. The blind side

And yet, of course, Obama was human; there were things he didn’t see, even when they were right in front of him. 

He’s largely dismissive of the Tea Party at first, since their arguments are fundamentally illogical and he has faith in the voters. He fails to divine a problem early on with Martha Coakley, the Democratic candidate running to replace former Sen. Ted Kennedy in Massachusetts; she loses and Obama loses his filibuster-proof Senate majority. He waits too long to dignify Trump’s birther conspiracy with an official White House response, allowing it to fester, until polls showed that 40 percent of Republicans didn’t believe he was born in the U.S. Belatedly, he asks Hawaii to release the longform birth certificate.  

Obama seems to have gotten the full measure of Mitch McConnell’s obstruction early on — translating most of his turtle-like utterances as “you must be confusing me with someone who cares” — yet still keeps plugging away as if he’s acting in good faith. He likewise has no illusions about Sen. Lindsey Graham — “Lindsey’s the guy [in a heist movie] who double-crosses everyone to save his own skin,” Obama recognizes in 2009 — yet lets him take point on a climate bill in the Senate. (To be fair to Graham, Obama did hamstring him by giving away drilling rights for oil companies without using it as a bargaining chip — another thing Obama doesn’t see.)   

6. The successor 

You can see why Obama didn’t want the book released before the election. Out of context, the revelation that Biden was against the Bin Laden raid might have been enough to peel some voters away from his former Veep. However, it has to be said that Joe emerges from this book looking pretty damn good. He’s a key voice in the room on all major decisions, and a guy who can squeeze compromises out of Congress against the odds. “In McConnell’s mind, negotiations with [Biden, on whether or not to extend the Bush tax cuts] didn’t inflame the Republican base.” 

Unless Democratic voters in Georgia can win both runoffs in January against the odds, the state of American politics may soon turn on whether McConnell still feels he can negotiate with Biden without inflaming the base. Given the increasing radicalization of that base in terms of rejecting the evidence of its eyes and ears, we have little cause to hope.

But let us not end this review of the memoirs of the ultimate proponent of hope on such a sour note. Let us think instead of the new-to-me fact that both Biden and Obama had ancestors who were shoemakers in Ireland, and that they emigrated to America weeks apart from each other. Now if that isn’t a historical buddy drama on HBO waiting to happen, I don’t know what is. 

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