The Enduring Grift of the Washington Operator

The Enduring Grift of the Washington Operator

Gambling With Democracy

How to make it in Washington.

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Among its many well-documented deficiencies, Washington, D.C., conspicuously lacks a robust tabloid press. Unlike Britain’s pioneering tabloid scene in London, Washington reporting, tasked with chronicling the fortunes of a putatively more expansive and less class-bound American social order, is a dreary exercise in chin-stroking deference and decorum. This condition is grimly distilled in the self-regarding pomposity of the motto adopted by The Washington Post, the market-dominating broadsheet owned by one of the richest men in the world: “Democracy dies in darkness.” While the city teems with open graft, influence peddling, corporate giveaways, and industry-subsidized think tanks, its reporters tend to cover the city as if it were the Parthenon. The dominant journalistic refrain holds that the people’s tribunes are always and forever seeking some mystic golden mean of self-canceling interests—even when they’re pursuing objectively demented aims, such as hijacking the phony mechanism of the debt ceiling to extort brutal budget cuts in the name of bipartisan comity.

Or to take another timely case in point: Supreme Court Justice Clarence Thomas and his wife have spent the past few decades accumulating all manner of feather-bedding dosh from big-name right-wing donors such as Texas real estate baron Harlan Crow and Federalist Society capo Leonard Leo. One can only imagine how a tabloid-minded D.C. news outlet might have tracked this egregious infestation of the high court by influence-seeking cash, but instead we’ve only learned about this benighted affair more than a quarter-century after the two men became close—and even then, in bowdlerized language depicting Crow as an exceptionally open-pocketed personal friend of the justice. The editors of the Daily Mail would justly greet such euphemisms with a torrent of bitter guffaws.

In The Big Break, the Washington Post reporter Ben Terris sets out to chronicle this other Washington, the one full of rank opportunism, low-grade hypocrisy, and free-form clout chasing. After years spent reporting on the city, Terris explains, he “wasn’t…interested in the politicians themselves (boring, busy, overexposed) as much as the people whispering in their ears, or trying to.”

A series of extended profiles, The Big Break focuses on the professional political enablers whispering into the ears of Republicans and Democrats alike. We meet people like Matt Schlapp, the head of the American Conservative Union and the chair of its annual Conservative Political Action Conference (CPAC), a notorious gathering of grifters and policy entrepreneurs that helped incubate Donald Trump’s presidential ambitions. We follow the career setbacks of Jamarcus Purley, a disaffected former member of Dianne Feinstein’s staff, who earned 15 minutes of social media notoriety for posting an after-hours video of himself in the California senator’s office dancing to the classic R&B stylings of DeBarge in a cloud of marijuana smoke. Then there’s Robert Stryk, a “cowboy diplomat” from Arizona who launched himself to the top rungs of D.C.’s lobbying scene by brokering an improbable post-inauguration cell phone call from the ambassador of New Zealand to President Trump. And there’s Leah Hunt-Hendrix, an heiress to the Hunt oil fortune who launched a political career from her participation in Occupy Wall Street, cofounding the progressive campaign-donor combine Way to Win.

This group portrait of Washington’s insider class reminds us that the city is not defined by selfless civil servants laboring virtuously on behalf of the public weal. Like any other company town, Washington is a hive of insatiable ambition trained on a series of moving targets—from the Global War on Terror to the Trumpian war on the peaceful transfer of power. For many seasoned political operatives, the name of the game is always to nimbly recalibrate your moral compass—and to demagnetize it the moment it might pose a threat to your return on investment.

Front and center in this rogues’ gallery of manic self-dealing and back-biting is Sean McElwee—in many ways the mascot of The Big Break, in both character type and career trajectory. After making a name for himself as a progressive political scene-maker in New York, McElwee set up shop in Washington in 2021, and his mid-Atlantic pilgrimage doubles as a morality play on the waywardness of D.C.-bred ambition. We meet him hosting his regular poker night at his D.C. apartment, delivering a running line of banter that is equal parts snark and self-promotion. (Sample laugh line: “I’m in the business of making Joe Biden’s agenda look more popular than it really is, and business is booming!”) Once planted in Washington, we are told, McElwee “managed to generate a gravity well, attracting other Democratic operators into his orbit”—everyone from Senate staffers and MSNBC correspondents to Gabe Bankman-Fried, the brother of the now-bankrupt-and-arraigned crypto mogul Sam Bankman-Fried.

McElwee is also the lead “gambler” in The Big Break’s subtitle—an obsessive bettor on elections as well as an aspiring shaper of their outcomes. It’s not an ethically tenable position, to put it mildly, but McElwee counts on the rudderless low-grade cynicism coursing through the Washington establishment to forgive his multitude of sins. When Terris asks him during the primary phase of the 2022 midterm cycle if he’s betting on the same races he’s working on, McElwee indulges in a dramatic pause, then laughs and answers, “Who can say?” It’s all part of the same hustle, in his view—which is why, for example, he brags to Terris and his poker buddies about the pair of luxe shoes he bought after betting against former Bernie Sanders surrogate Nina Turner’s congressional campaign in Ohio. “I was polling for Nina Turner’s super PAC,” McElwee announces. “So I knew Shontel Brown was going to win.”

Hardy fucking har. McElwee’s shtick, like so much of the insider patter in Washington, ultimately rests on the belief that anyone who still expects the city’s politics to address the plight of ordinary Americans in a starkly unequal economy is either a sucker or a rube. Media critic Jay Rosen has called this the purblind worship of savviness as a self-evident political good. McElwee’s devotion to it is probably the surest sign that he has successfully adapted to Washington.

A close second would be McElwee’s tight strategic alliance with Gabe Bankman-Fried, who ran a super PAC for the family’s pet cause of pandemic preparedness and helped sluice tens of millions of dollars into Democratic campaign coffers during the 2022 midterms. McElwee bragged to all that it was “cool as hell” to be advising the Bankman-Frieds and even professed allegiance for a few months to “effective altruism”—the quack-infested philosophical movement that both guided the Bankman-Frieds’ philanthropic strategy and rationalized their massive speculative fortune.

McElwee and the Bankman-Frieds had arrived in D.C. at the right moment: It was an era of new possibility in the Trump-battered capital, and the Democrats were eager to find a group of youthful policy entrepreneurs who could help secure some long-deferred wins for disaffected liberals. But just as the Biden administration began to clock some significant legislative victories, all three men found their own fantasies of influence unraveling. In the fall of 2022, Sam Bankman-Fried’s crypto exchange FTX collapsed after a panicked run of withdrawals, taking his brother Gabe’s super PAC with it. Meanwhile, after the 2022 midterms, McElwee had his own moment of reckoning: He was ousted by his employees at Data for Progress after the nonprofit incubator that sponsored the firm learned that McElwee had furtively launched a for-profit crypto-industry side hustle within it, and as reports continued to spread that he was using its data to fuel his own gambling habit. “I felt like an asshole because I went with it,” one of McElwee’s lieutenants confides to Terris in the aftermath. “But when he says it in rooms of people and everyone just laughs, what am I supposed to think?”

That question haunts the rest of Terris’s biographical studies: What are we supposed to make of them? As Trump closed in on the presidency in 2016, Matt Schlapp rushed to reinvent himself from a mainstream GOP Trump skeptic to a full-on master of MAGA agitprop. In this regard, Schlapp serves as a conservative avatar of the city’s broader reinvention in Trump’s glowering orange image—the “boom time for weirdness in Washington,” as Terris puts it. Schlapp, despite his role as CPAC’s ringleader, had staked out a position as a “reasonable” conservative in D.C.’s punditsphere, going into regular rotation on the liberal cable network MSNBC. And in October 2016, the infamous Access Hollywood tape of Trump bragging about his track record of sexual assault triggered a brief crisis of conscience for Schlapp—at least as Terris tells it. Schlapp pondered breaking with the GOP presidential nominee for the sake of his five daughters, but finally one of them—a true adept of Beltway reasoning—put an unanswerable question to her parents: Why would they do anything to help Hillary Clinton?

Running with that logic proved incredibly lucrative for Schlapp, who saw the revenue for his lobbying shop, Cove Strategies, skyrocket from $600,000 the year before Trump took office to $2.4 million in the final year of his presidency. But that Trumpward pivot came with many hidden costs—and Schlapp’s eventual D.C. downfall proved to be as karmically rich as McElwee’s. On Schlapp’s MAGA-fied watch, CPAC descended deeper into the recesses of unhinged conspiracy mongering and bigotry—and the heavy-drinking Schlapp reportedly tried to seduce a male staffer for Georgia Senate hopeful Herschel Walker in the final days of the 2022 race. He is now facing a civil lawsuit as a result.

Trumpworld lobbyist Robert Stryk is another of the MAGA hangers-on whom Terris profiles. Stryk had sped through D.C.’s revolving door after a brief stint as an aide to Republican Arizona Congressman Jim Kolbe and had scored some early consulting and lobbying successes during the George W. Bush years, only to see much of his client base dry up when the Democrats came to power in 2009. Stryk got an early leg up in Trump’s 2016 campaign by running its organization in the noncompetitive state of Oregon, and he acquired additional clout by recommending a former colleague in Oregon politics, a lawyer named Jacob Daniels, to serve on Trump’s campaign, where he went on to serve as the deputy for its successful Michigan operation. After inadvertently granting New Zealand’s ambassador a phone audience with Trump after the election, Stryk was back in the limelight: The New York Times Magazine featured him in a story headlined “How to Get Rich in Trump’s Washington.”

But his tour as a heavy hitter in D.C. proved to be remarkably short-lived. During Trump’s chaotic final year in office, Stryk’s firm, the Sonoran Lobbying Group, succumbed to long-simmering internal tensions. All of his staff had scarpered, as had 15 of the firm’s 21 international clients. Determined not to repeat the career nosedive of 2009, Stryk went scrounging after increasingly unsavory clients: Belarusian allies of Vladimir Putin’s Ukraine invasion; Isabel dos Santos, the daughter of Angola’s former president and (not coincidentally, it seems) the richest woman in Africa; and a convicted GOP child molester named George Nader.

But it was Stryk’s contract with Venezuelan President Nicolás Maduro, successor to the country’s Hugo Chávez regime, that finally stirred the ire of right-wing politicians such as Florida Senator Rick Scott, who suggested a boycott of Maduro’s lobbyists—another reminder that the only sort of corruption that won’t be tolerated in Washington is the kind that crosses party lines. Amid his trials, Stryk abruptly cut off contact with Terris, but not before insinuating in their text exchanges that the Post reporter might be a child molester—a favorite refrain of the QAnon wing of the Trump coalition, even as Stryk was lobbying to get a presidential pardon for the bona fide child predator Nader.

Such are the head-spinning rites of belonging and exile, sucking up and reprisal, that Terris digs out from his patient rounds of reporting among the aspirational D.C. power elite. The Big Break is at its strongest, however, when its protagonists don’t blindly careen into their professional reckonings, as McElwee and Schlapp do, but instead choose to disengage from the D.C. game on something closer to their own terms.

Schlapp’s longtime CPAC lieutenant Ian Walters faced a bout of social media backlash when he delivered some ill-considered remarks about hiring a Black RNC chair from the CPAC stage—but in its aftermath, Walters didn’t clamor to be recognized as a martyr to “cancel culture,” as Schlapp did. Instead, he dropped out of Schlapp’s operation, picking up gigs as a musician and holing up in his rural Maryland home. And when Walters saw Schlapp deliver a crass Trumpian eulogy at his stepfather’s funeral in late 2020, he finally opted out of the ideological messaging industry.

In the book, Terris asks Walters whether he regrets his long alliance with CPAC, and Walters offers a fairly standard alibi among older-line members of the GOP: that when he became affiliated with Schlapp and the conservative movement that helped launch Trump’s presidency, he did so to exert an important guiding influence on a political tendency otherwise inclined to go off the rails—“doing the work to keep out the bad actors, trying to give sensible advice,” Terris writes. But as the reporter probes further, he comes to realize that “‘Ian’s story in its own small way was the story of the Republican party”:

It was true that Trump rose to power with the help of some mega-enablers—the Schlapps, who saw an opportunity for influence: Stephens Bannon and Miller, who saw him as a vehicle for their nativist worldview. But there could never have been a Trump without millions of Ians—those who cast their votes for him twice before seeing what he’d been making plainly obvious for as long as he’d been in the political arena.

In other words, the professionally savvy foot soldiers of the political scene are as often as not the suckers and the rubes—at least in a right-wing power structure that demands complete fealty to a cult of personality. That’s partly why Walters is unable to grace Terris with any kind of post-Trump redemption narrative: “I’m not a hero,” he admits. “If anything, I was too slow. Walking away was a concession of sorts. I lost.” And amid all the more spectacular career flameouts in Terris’s book, the grimmest denouement comes when Walters ventures back into freelance conservative consulting work, taking on former Christian Coalition head and erstwhile Jack Abramoff crony Ralph Reed’s new Faith and Freedom Coalition as a high-profile client. Among his other well-chronicled sins, Reed is also a premier Trump booster on the religious right. When Terris again asks Walters how his conscience is faring, he gets more industrial-grade moral temporizing:

“I believe in the way I operate, in the techniques I’ve developed to persuade people to listen to their better angels and do right by their fellow man,” he said. He could simply tell the whole political system to screw off, he said. But if everyone like him left the conversation, then that would leave all the talking to the worst actors in politics.

Terris rightly calls bullshit on this soliloquy: “It was Ian’s answer for why he’d stuck around CPAC as long as he did. He was spinning again.” But this, too, is a permanent condition of D.C. discourse—all crises are fodder to be managed, including crises of conscience. The self-distancing and self-delusional rhetoric employed and refined by members of the messaging class exists largely to conceal their baser motives from themselves—and to always allow themselves the provisional alibi of managing things better than a hypothetical replacement-level apparatchik would.

This self-exculpating line of argument is the same general alibi that the disgraced McElwee gamely floats after his downfall. “His departure,” Terris tells us, describing McElwee’s perspective, “was the result of an overreaction by a young, progressive staff, who had grown frustrated by his pragmatic politics and then ‘got freaked out’ by what people were saying about him on Twitter.” Only McElwee being McElwee, he didn’t bother invoking the better angels of anyone’s nature: “If people think they have seen the last of me,” he tells Terris, “they should know I’m a tenacious motherfucker.”

Well, a motherfucker at the least. Early on in my advance copy of The Big Break, I started marking this or that attention-grabbing McElwee quote—such as his gleeful declaration that he was a “Clarence Thomas Democrat,” because his relentless pursuit of big-donor cash was sanctioned by the Supreme Court’s 2010 ruling in Citizens United v. FEC, which unloosed the dark-money spigots across our already cash-infested political system—with the marginal notation “what a fucking tool.” (Another, admittedly more pedantic reason this particular outburst was so grating is that it was Anthony Kennedy, not Thomas, who wrote the majority opinion in Citizens United.) But the occasions for it grew so frequent that I eventually resorted to the abbreviation “WAFT.”

My arm’s-length readerly exasperation with McElwee’s faux-scandalous patter of course pales in comparison to what his workforce must have endured as he cajoled them into placing their own election bets and browbeat them into hewing to the pragmatist/”popularist” gospel. Worse still must have been the trials of McElwee’s former longtime girlfriend, who can’t have been pleased to see him discussing in the book how he’d cut her out of his life because he didn’t think she could handle his success. “I’m not particularly emotional about it,” McElwee tells Terris. “Or about anything, really.” But he does enthuse that “me and David Shor”—the other progressive-branded pollster turned self-serious “popularist”—“are going to have a hot boy summer.”

Early on in The Big Break, Terris writes that he was drawn to the book’s dramatis personae because “politics was personal for them.” But as the reader patiently tracks the tangled, power-occluded elective affinities of figures like McElwee, Schlapp, and Stryk, it seems that the obverse is the case: Politics is often their theater of personal evasion. It’s the blunt instrument they use to assuage—or shun—the gaping voids in what political civilians might call their souls. And Washington itself may not be the culprit behind all this rampant character deformation so much as a somewhat arbitrary filtering device—a means to channel unbridled ambition into some officially sanctioned channels, while letting all manner of raging narcissism and other unfulfilled longings fester behind the scenes.

In this respect, Trump himself may not have been the great change agent that the narrative conceit of Terris’s book makes him out to be; he, too, was another developmentally stunted opportunist, ineluctably drawn to a city on the make, one that’s constructed to reward rather than rein in debilitating character flaws. If Washington had ever bothered to support a vigorous tabloid press, we might have understood all this much more clearly back in 2016, when the Trump takeover of D.C. was on virtual autopilot. For the moment, the bracing insights and gimlet-eyed reporting of The Big Break will have to suffice.

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