It is amazing how complete is the delusion that beauty is goodness.

— Leo Tolstoy

“Even Scaled Back,” wrote Vanity Fair, “Barack Obama’s Birthday Bash Is the Event of the Season.” Not even the famed glossy Bible of the unapologetic rich seemed sure of whether to write Obama’s Birthday bash straight or as an Onion headline: what did the “Event of the Season” mean during a pandemic?

A former president flying half the world’s celebrities to spend three days in a maskless ring-kissing romp at a $12 million Martha’s Vineyard mansion, at a moment when only a federal eviction ban prevented the outbreak of a national homelessness crisis, was already an all-time “Fuck the Optics” news event, and that was before the curveball. Because of what even the New York Times called “growing concerns” over how gross the mega-party looked, not least for the Joe Biden administration burdened with asking the nation for sober sacrifice while his ex-boss raised the roof with movie stars, advisers prevailed upon the 44th president to reconsider the bacchanal. But characteristically, hilariously, Obama didn’t cancel his party, he merely uninvited those he considered less important, who happened to be almost entirely his most trusted former aides.

Cast out, the Times said, were “the majority of former Obama administration officials… who generally credit themselves with helping create the Obama legacy,” including former top aide David Axelrod, who’d just called Obama an “apostle of hope” in the Washington Post and sat for a three-hour HBO documentary deep-throat of his ex-boss. Remaining on the list were celeb couples Chrissy Teigen and John Legend, as well as Dwyane Wade and Gabrielle Union, along with Steven Spielberg, George Clooney, Tom Hanks, Bruce Springsteen, Questlove, Jay-Z, Beyoncé, Don Cheadle, and other Fabulous People, who drank “top shelf liquor,” puffed stogies, and hit the links at the Vineyard Golf Club (membership fee: $350,000). An early report that Pearl Jam had been hired to perform was later refuted. Eddie Vedder would be there, but not to play.

One attendee called it the “party of all parties,” while another added, “Y’all never seen Obama like this,” by which he might have meant Obama reportedly dancing as Trap Beckham, performing live, substituted “Prez” for “Bitch” in this classic:

It's all about you
Girl tonight it's about you…
Fuck it up if it's your birthday bitch!

There’s a glorious moment in the life of a certain kind of politician, when either because their careers are over, or because they’re so untouchable politically that it doesn’t matter anymore, they finally get to remove the mask, no pun intended. This Covid bash was Barack Obama’s “Fuck it!” moment.

He extended middle fingers in all directions: to his Vineyard neighbors, the rest of America, Biden, the hanger-on ex-staffers who’d stacked years of hundred-hour work weeks to build his ballyhooed career, the not quite A-listers bounced at the last minute for being not famous enough (sorry, Larry David and Conan O’Brien!), and so on. It’d be hard not to laugh imagining Axelrod reading that even “Real Housewife of Atlanta” Kim Fields got on the party list over him, except that Obama giving the shove-off to his most devoted (if also scummy and greedy) aides is also such a perfect metaphor for the way he slammed the door in the faces of the millions of ordinary voters who once so desperately believed in him.

Obviously, getting rich and not giving a shit anymore is the birthright of every American. But this wasn’t supposed to be in the script for Obama, whose remarkable heel turn has been obscured by the Trump years, which incidentally were at least partly his fault. The history books and the still-starstruck press will let him skate on this, but they shouldn’t.

Obama was set up to be the greatest of American heroes, but proved to be a common swindler and one of the great political liars of all time — he fooled us all. Moreover, his remarkably vacuous post-presidency is proving true everything Trump said in 2016 about the grasping Washington politicians whose only motives are personal enrichment, and who’d do anything, even attend his wedding, for a buck. Trump’s point was that he, Trump, was already swinishly rich, while politicians have only one thing to sell to get the upper class status they crave: us.

Obama did that. He sold us out, and it’s time to start talking about the role he played in bringing about the hopeless cynical mess that is modern America.

I fell for it. In 2007 and 2008, as Obama crisscrossed the country organizing a bold palace coup to snatch away the Democratic Party from the Clintons, I took the bait. Sent to trail him for Rolling Stone, I recognized I was witnessing a brilliant marketing campaign, a political magic trick, but talked myself into believing the illusion was for the good of the country, and the world.

Reader, I was skeptical. Though his increasingly lovesick crowds believed they were finally witnessing the arrival of the long-awaited agent of real fundamental change, I was careful at every stop to note this was “not necessarily a reflection of who or what Obama really is.” Obama’s appeal, I wrote, was “a mood thing, not an issue thing.” I refused to describe his speeches as idealistic, because “Obama isn’t selling idealism so much as a kind of reinvigorated, feel-good pragmatism.” In interviews with awed supporters, I always pushed for specifics, as in this scene in Portsmouth, New Hampshire:

“There’s just something about him,” says one middle-aged gentleman.
When I suggest that his comment is vague, he shrugs.
“Yeah, but it’s good vague.”

Again, history books will not recognize it, but Obama previewed Donald Trump’s campaign, or at least a version of it, selling himself as an untainted outsider challenging a failing and mistrusted political establishment. Campaign reporters initially ripped him for his “lack of experience” and “rookie mistakes,” not realizing these descriptors were pluses for an electorate that had soured on both traditionally “electable” politicians and the media gatekeepers who puffed them up. As with Trump, when Obama defied early pundit predictions to surge toward the lead, he won over voters desperate for a sign that “not everything in our politics is rigged,” as I wrote back then, referencing a word that the candidate himself occasionally used.

2008 Obama from the jump hammered the Trumpian theme of a payola system that froze out the regular person:

They write the checks and you get stuck with the bills, they get the access while you get to write a letter, they think they own this government…

Already in 2008, I wrote, “no crisis is more desperate than the spiraling level of general disbelief of our political system.” Debacles in Iraq and New Orleans and passage of grotesqueries like the Bankruptcy Bill and the Medicare Modernization Act left voters believing Congress and the Cabinet were little more than “a low-rent crime family hired to collect protection money for the likes of Halliburton and Pfizer.” The post-WMD press tried early on to hype the 2008 race as a profound clash of opposites, but a stunning 56% of likely voters agreed with the phrase, “The presidential election is annoying and a waste of time.”

Voters were approaching the upcoming election “with the enthusiasm of a two-time loser offered a selection of plea deals.” Obama answered this malaise with stump speeches carefully crafted to cast Hillary Clinton as the standard-bearer for a Washington political class hopelessly out of touch, and sick with its own sense of entitlement. “I’m not running for president because I think this is somehow owed to me,” Obama would say coyly, never mentioning Clinton by name.

John Edwards served as an unofficial running mate, lurking as a “crucial character in a Hillary death drama,” a fiery Cassius to Obama’s contemplative Brutus. Playing the role of the small-town favorite son returned from Rome with tales of unspeakable aristocratic treachery, he tore at Hillary’s flank with heavy doses of class resentment, describing her as an elitist indistinguishable from George W. Bush, while imploring voters not to “trade corporate Republicans for corporate Democrats.” Hillary was unable to contain her disgust at this treachery, often coming across in the presence of either man like “an angry drag queen, enraged that some other tramp has been allowed to sing Danke Schoen” on what should have been her Vegas stage.

Hillary knew what most voters did not, that Obama was vacuuming mountains of cash from the same places she was, with future bailout recipients Citigroup and Goldman, JP Morgan Chase and Morgan Stanley all among his top donors. Previewing his current career as a uniquely gifted post-presidential profiteer, Obama in 2008 was a spectacular fundraiser, quietly setting the stage to become the ultimate defender of the status quo, even as he publicly ran against it.

He was so skilled at selling the appearance of a course change from payola and partisan gridlock that I recorded Democratic voters in his crowds comparing him in a complimentary way to Ronald Reagan, while another of his supporters told me with a straight face she couldn’t vote for Hillary because she represented the “old boys’ network” in Washington.

I saw that Obama was really just “a typical middle-of-the-road Democrat with a lot of money and a well-run campaign,” but by November of 2008 I’d convinced myself the mere fact of his campaign was a great historical triumph. He’d restored the public’s confidence just as our international reputation was disappearing down the sinkhole of the Iraq disaster. Moreover, at the exact moment the Katrina catastrophe had put the “two Americas” narrative on television, graphically demonstrating how little real progress we’d made since the sixties in desegregating the country, the sweeping nature of Obama’s victory provided hope that the country could finally conquer its racial demons.

On Election Night in 2008, which I spent at John McCain’s “victory” party in Arizona, I spent an hour sitting next to the mostly ignored hors d'oeuvres table, talking myself out of cynicism. Watching the ecstatic crowds at Grant Park on TV, I decided it didn’t matter who Obama was, underneath. As a symbol alone, he was an awesome success who’d brilliantly re-energized the American experiment, expunging the feeling of inevitable imperial decline that hung over the country, while offering a future that seemed more full of possibility. All he had to do, to win a place in history books as a great unifier, was not make a mockery of two words he’d all but copyrighted in that campaign, hope and change.

Many Democrats remember vaguely that the early Obama years were a disappointment, but the memory has been glazed over by a propaganda point: it wasn’t his fault. Tilting at the windmill of a corrupt Washington establishment, his talk about learning to “disagree without being disagreeable” shattered by viciously obstructionist Republicans and race-baiting Fox audiences, Obama accomplished what he could, which wasn’t much.

The reality is much more grotesque. Obama sold out the instant he moved into the White House, before the likes of Mitch McConnell even had a chance to figure in the picture.

Example: as mentioned here before, Obama as a candidate had run an ad denouncing Louisiana’s Democratic congressman Billy Tauzin for taking a $2 million job at the the drug lobby firm PhRMA right after passing a monster prescription drug handout bill. “That’s an example of the same old game-playing in Washington,” Obama said, in an ad called, Billy. “I don’t want to learn how to play the game better. I want to put an end to the game-playing.”

Immediately after Obama took office — between February 4th and July 22nd of 2009, to be exact — “Billy” became a regular visitor to the White House, visiting an average of once every 15 days. Those meetings culminated in a deal struck between the Obama White House and PhRMA, in which the trade group would donate $150 million to lobby for the passage of Obamacare, and Obama in return would abandon two of his key campaign pledges (among other things): allowing Medicare to negotiate pharmaceutical prices in bulk, and allowing citizens to import cheaper drugs from Canada. Right out of the gate, Obama’s signature bill was built atop the exact slimeball game-playing, with the exact slimeball players, he pledged to avoid.

Every politician breaks promises, but the issue with many of the items in Obama’s long list of reversals was not failure but betrayal, in the most profound and devastating sense of the word. I was relatively a booster of Obama in 2008, but once assigned to cover the financial crisis found myself stunned at choices he made, beginning with the appalling decision to invite still-employed Citigroup officials to run his economic transition. This move led to one of the more breathtakingly corrupt deals in modern presidential history, one the press gave almost a complete pass. I heard about it from a senior Democratic Party official, a great believer in Obama who was flabbergasted by the lack of press attention and still I think hopeful on some level that the King simply didn’t know what was going on at his court.

Obama hired his close friend and Harvard law classmate Michael Froman, a protege of former Bill Clinton Treasury Secretary Bob Rubin, to run his economic transition team. Froman was a Citigroup executive who made $7.4 million at the company in 2008 and did not resign when he joined the transition team. This is significant because less than a month after Obama’s election, on November 23rd, 2008, a deal was struck to give a $306 billion bailout to Citigroup, a rescue negotiated in significant part by Timothy Geithner, another former deputy to Rubin.

Some background is required to understand the full depth of the betrayal. Rubin, along with Clinton and former Fed chair Alan Greenspan, had been instrumental in repealing the Glass-Steagall Act, a 1930s law which prohibited the merger of commercial banks, investment banks, and insurance companies. In the 1990s, that law ostensibly stood in the way of the Citigroup merger, which united Salomon Brothers, Citibank, and Travelers.

I say ostensibly because the Citi CEO Sanford Weill simply concluded the merger extralegally, thanks to what was essentially a Papal indulgence from Greenspan, who temporarily blessed the deal in 1998 pending congressional action. With a big push from Clinton, Rubin, and Froman (who was Rubin’s chief of staff from 1997-1999), and tangentially Geithner (who also worked under Rubin in the Clinton Treasury), the Glass-Steagall Act was finally repealed via the passage of the Gramm-Leach-Bliley Act, which legalized the Citigroup merger post-factum.

Once the Citi merger went through, Rubin and Froman immediately went to work at the new super-bank. Rubin was paid CEO wages at $115 million per year for a job Citi itself described as having “no line responsibilities.” Nonetheless, Rubin did have a senior position at the bank, which by 2007 had accrued $43 billion in toxic mortgage assets, a major part of the reason the company eventually needed a bailout.

Follow the bouncing ball: it’s November of 2008, and Citigroup, Rubin, and Froman are headed down the drain of history. The company is rescued when Froman is hired by the incoming president, an old college buddy, and another former protege of Rubin’s, Geithner, negotiates aggressive intervention by the Federal Reserve bank to flood the essentially bankrupt company with cash. Now for the good part: before the Citi bailout was even announced, Timothy Geithner was hired by that still-employed Citigroup executive Michael Froman to be Barack Obama’s Treasury Secretary. Citigroup then turned around and — after the bailout — gave Froman a $2.25 million year-end bonus. Another Citi official who’d gone to work for Obama, future Treasury Secretary Jack Lew, got a $940,000 bonus after the negotiated bailout. When news of this got out, it was finally a bridge too far, optics-wise, and Froman at least pledged to give the last bonus check to charities “related to homelessness and cancer.”

I reported on all of this with some disappointment — I still liked Obama and was in a state of disillusionment — in a much-criticized Rolling Stone piece called Obama’s Big Sellout. I mention this only because this sequence of events later offered me an unfortunate window into the personality of the president. Years later, Obama gave an interview to Rolling Stone in which he gently castigated the magazine (read: me) for its coverage of his Wall Street policy. The relevant portion:

Q: Forget for a moment about obstruction by Wall Street lobbyists and Republicans in Congress. If you could single-handedly enact one piece of regulation on the financial industry, what would it be?
OBAMA: The story of Dodd-Frank is not yet complete… I’ve looked at some of Rolling Stone’s articles that say, “This didn’t go far enough, we didn’t institute Glass-Steagall” and so forth, and I pushed my economic team very hard on some of those questions. But there is not evidence that having Glass-Steagall in place would somehow change the dynamic. Lehman Brothers wasn’t a commercial bank, it was an investment bank. AIG wasn’t an FDIC-insured bank... So the problem in today’s financial sector can’t be solved simply by re-imposing models that were created in the 1930s.

This was classic Obama: he said he pushed for Glass-Steagall “very hard,” then in the same breath said it wasn’t important or needed, before proceeding to name a few key companies Glass-Steagall would not have impacted (like AIG and Lehman Brothers) while ignoring the many big crash actors it would have, especially Citigroup.

One of the most shameful transactions of his presidency, the backdoor rescue of Bob Rubin and Citi, flowed from the bribe-laden repeal of Glass-Steagall, but this politician was so certain of the hold he had over liberal audiences — he was correct in this — that he never feared to bring up the topic in conversation. That he chose instead to grouse over an extraordinarily rare instance of serious criticism of him from the blue side of the aisle showed the weirdly petty side of his character.

I could go on about Obama’s betrayals and broken promises, which included the expansion by this would-be gentle constitutional lawyer of both a brutal drone murder program and a vast illegal surveillance operation, the instantly violated pledge to have no registered lobbyists in the White House (Obama brought former Goldman lobbyist Mark Patterson in to serve as Deputy to Geithner right after inauguration), the ignored promise to close the Guantanamo Bay prison, the waived plan to “put on a comfortable pair of shoes” and walk with union members in a picket line (he never did this), the decision to make the Bush tax cuts permanent while blowing off promises to lift the payroll tax cap above $250,000, or end the carried interest tax break, the repeated use of the Espionage Act to bully non-compliant reporters and their sources, and so on, and so on.

Just yesterday the Washington Post published an excerpt from a new book about the “baldfaced” deception of December 28, 2014, when Obama furled the green flag of coalition forces in Afghanistan to mark the supposed end of our “combat mission” there, in what he called a “milestone for our country.” This was despite the fact that the Administration never had any intention of leaving Afghanistan, and didn’t, and systematically covered up our failures there.

Obama’s handling of the aftermath of the financial crash proved a prolonged textbook case of what Trump in 2016 would later denounce as “insiders fighting for insiders.” Obama’s Attorney General Eric Holder, a bank lawyer whose corporate defense firm Covington & Burling represented nearly every one of the worst actors in the financial crisis, and which literally kept an office open for him during his entire temporary assignment as the nation’s top law enforcement official, did not successfully prosecute a single senior finance official connected with the 2008 crash.

Holder, who as a young lawyer in the Clinton Justice Department had invented the “Collateral Consequences” theory that government should find non-prosecutorial solutions for large employers, told the Senate in 2013 that the systemic importance of companies like HSBC (which had just been caught laundering nearly a billion dollars for drug lords) had “an inhibiting impact” on his ability to conduct prosecutions. As a result, the Obama Justice Department moved instead to pioneer numerous new forms of soft-touch relief for the super-rich, including multi-billion-dollar settlements that did not require the signature of a judge, a kind of formalized back-room deal.

In 2008, Obama uplifted centrist Democrats and leftists alike. After that, when he became most of the things he promised never to be, he retained admiration from progressives because he was still a winner who kept hated Republicans out of the White House. Books like Double Down: Game Change 2012 by high priests of conventional wisdom like John Heilemann and Mark Halperin cut a new style of heroic dress for the former Captain Hope-and-Change.

No longer an inspirational icon, he was now a cold-blooded assassin — literally. “Turns out I’m really good at killing people,” he said, about his drone program. “Didn’t know that was gonna be a strong suit of mine.” On a more metaphorical level, he was now said to be a great political infighter who “in every instance,” under “ungodly pressure,” would drain “the three pointer at the buzzer,” as the authors said. They described Obama’s comeback after a disastrous first debate performance against Mitt Romney as a masterwork. When Romney charged that America’s navy had fewer ships than in 1916, Obama countered that the army had fewer horses, too. Another three pointer! “You know,” Obama said backstage, “I really have figured this out.”

The problem with this version of events is that in a broader sense, Obama’s post-2008 transformation back into the ultimate Washington insider was a major factor in Donald Trump’s election.

So much attention was paid to the xenophobic angles of Trump’s stump speeches in 2016 that almost no one noticed how heavily he borrowed from Obama. Both men stressed the American dream slipping away, both promised a stop to endless war, both stressed talking to traditional enemies rather than shutting them out (“Doesn’t make us look tough, it makes us look arrogant,” said Obama), both played at being economic populists. Obama dominated at the ballot in part because with these appeals he won white middle-to-working class voters in districts that had mostly been lost to the Democratic Party since the Reagan years. He lost them all over again in his eight years. Nine percent of Obama’s 2012 voters switched to Trump in 2016, and another 7% stayed home.

Obama himself recognized what Trump had done. After Trump won, Obama from Greece lashed out at Hillary Clinton for failing to compete in “lost” territory, and for not recognizing the “powerful stuff” Trump was bringing to people who were “feeling deeply disaffected.” He chided Hillary for not realizing that “we have to deal with issues like inequality… and economic dislocation,” and that winning means going to “every small town and fair and fish fry and VFW hall” in order to lose in some places by “20 points instead of 50 points,” as he’d done.

In Obama’s telling, it was Hillary’s nose-in-the-air campaign strategy that was at fault, and he was right about that, to a degree. On another level, Obama lost those districts for Hillary, through his countless betrayals and nakedly patrician policies, though it was Hillary’s own voracious speech-profiteering for banks like Goldman, Sachs that made the more obvious political target.

Despite all of this, when Trump was elected I again talked myself into the idea that the Obama would end up looking pretty good someday, especially compared to his successor. I reasoned that one of the president’s most important jobs was to be a model in personal comportment, and Obama, for all of his profound political disappointments, had managed an extraordinary trick as the nation’s first black president. Forced to walk a constant media tightrope, in which it was demanded that he show the patriotism and strength to lead troops on the one hand, but also had to head off stereotypes about angry black men by never rising to the bait over monster provocations like Trump’s birther rants, Obama showed immense public discipline:

From a personality standpoint, Obama is everything Trump isn't. He's in control of his emotions, thick-skinned, self-aware, ingratiating, strategic, and temperamentally (if not politically) consistent. A striking quality of Obama as president is that he did his job without seeming to need to take credit for things all of the time, which kept the political price down on many of his decisions… To use a hokey sports metaphor, he did his job in the manner of an offensive lineman: the less you heard about him, the better he was probably doing.

Yes, I thought, he was a sellout and opportunist, and just a slick version of a typically amoral Washington machine pol, but as a behavioral model for young people, and particularly for young black people, there were still things to admire about Obama. In hindsight I was still remembering the young, trim, handsome pol, so different from “the bloated hairy shitbags we usually elect,” whose cool, rational manner had once taken me in. Tolstoy was right, we never stop falling for a pretty face. As he left office I was sure even his mixed legacy would age well, in the light of what was sure to be a chaotic Trumpian reign.

This was before I knew that Obama would immediately start monetizing his name with a battery of $400,000-per-hour speeches to Wall Street, and also before I knew the incredible details of his May, 2016 trip to Flint, Michigan. The city had been plagued by outbreaks of Legionnaire’s Disease and lead poisoning, with children sickened with neurological and behavioral problems, after years of drinking and bathing in poisoned water in as pure an example of sociopathic negligence as we’ve seen in American governance. Flint was true Evremonde politics, the kind of gross mistreatment that inspires revolutions, leaving people with nothing but rage for their injured children.

When Obama came to town, residents of the predominantly black city expected him to ride to the rescue by declaring a federal disaster and sending in FEMA for a cleanup. Instead, he told a story about how he was sure he ate lead paint as a kid (and turned out fine!), then took a micro-sip of Flint water, as if to show how safe it was. When the assembled gasped in horror, he chuckled with annoyance, “This is a feisty crowd tonight!” After, he held a quick presser where he repeated the sipping trick and zipped back to Air Force One in his limo. The scene is as close to pure political evil as you’ll ever see on stage.

It’s absolutely true that Obama was on the business end of outrageous abuse throughout his tenure as president, surrounded by jackals and media hacks and right-wing trolls who in thinly-veiled racial caricatures did things like deride him as a “Santa Claus” who won elections because he promised free stuff to his layabout followers. One could understand turning cynical in the face of enough of this, shutting the door on those parts of the country that rejected him in order to collect checks and throw parties.

But Obama didn’t eventually turn to the dark side. He sold us out on policy immediately after taking office, began personally cashing in the instant he was out the door, then essentially vanished, remaining involved in public life in only the pettiest, most limited way possible. To wit, he picked up the phone at the 11th hour of a contentious 2020 Democratic primary and brokered a serpentine deal to make sure his dummy veep got the nomination instead of a Vermont socialist whose entire platform was an implicit criticism of his, Obama’s, presidency.

Otherwise, Obama has been ostentatious in his near-total disinterest in the country he left behind, showing almost no public leadership in five of the most difficult years of its history, holstering his legendary communications skills during years of spiraling acrimony and division.

Worse, Obama has now displaced the Clintons as the ultimate example of the modern political profiteer. We now automatically assume Senators and presidents will spend their retirements pursuing every conceivable moneymaking opportunity while living lives of hoggish exclusivity. No more Jimmy Carters living in $167,000 homes, driving 1983 Mercury Capris and volunteering to build houses in between negotiating African peace treaties. The White House is now first and foremost a seat of financial power, its occupant by design an apprentice member of the 1%, who’s expected to accept full entrance into the wealth archipelago upon exit.

Trump won in 2016 because America preferred someone who was already a pig to someone merely on the way to being one. The country didn’t reach that level of cynicism on its own. Disillusionment has a cost, and Barack Obama transforming from symbol of hope and possibility to whatever he is now — to a shallow, conceited, Fat Elvis version of a neoliberal washout — has been a hell of a blow, whether America’s ready to admit it or not.

The Vanishing Legacy of Barack Obama