The Big Break

Prologue: Is Any of This Normal?

I’m in the business of making Joe Biden’s agenda look more popular than it really is,” Sean McElwee announced to the poker table. “And business is booming!”

It was a July evening in 2021. Biden’s presidency was six months old, his approval rating was hovering around 50 percent, and his agenda was on the move. Sean, the twenty-eight-year-old head of a Democratic polling group and think tank, was a few Miller High Lifes into one of his regular poker nights hosted at his bachelor pad in Logan Circle—a recently gentrified neighborhood in Washington, just north of downtown. In the living room, a big-screen television played Rounders, the 1998 Matt Damon poker movie that was canon among Millennial gamblers. A guest bed lay in the corner. Extra-large pizzas and cheap beer cluttered the counter in the kitchen, and tubs of protein powder sat on the shelves.

Sean was new to Washington—and splitting time with New York City, where he kept an apartment—but he had the vibe of someone who’d been around forever. He wasn’t a pollster exactly (he hired experts to do the legwork there), and he wasn’t a policy nerd. He wasn’t a campaign guy either (although his nonprofit, Data for Progress, did do work for campaigns). He was sort of all of these things and also sort of none of them. More than anything, he was a political evangelist. He was in the business of making Democrats popular—figuring out what legislation to prioritize, what phrases to stop saying. And he was in the business of making himself popular too.

Since moving to town a few months earlier, Sean had managed to generate a gravity well, attracting other Democratic operators into his orbit. He hosted monthly happy hours that were well attended by professional progressives and establishment climbers. The boozy meetups were a way to see people and be seen, and it was hard to miss Sean. He was over six feet tall with a body type that fluctuated between lineman and linebacker. He had a signature look: translucent-framed glasses and black T-shirts—an outfit he deviated from just enough to avoid comparisons to Steve Jobs or, worse, Elizabeth Holmes. Sean knew everyone, and every few weeks he invited a rotating cast of his happy-hour crew over for poker.

Tonight’s table featured: a spokesman for Facebook (“I work for our tech overlords,” he said); a friendly former Senate staffer who now led an organization attempting (unsuccessfully) to end the filibuster; a former top aide to former Senate Majority Leader Harry Reid; a senior reporter who covered the Senate for MSNBC; and Gabe Bankman-Fried, the brother and political consigliere of the crypto billionaire Sam Bankman-Fried.

Like any effective Washington operator, Sean was good at getting close to people with money—or at least close to people who were close to people with money. Sean wasn’t ultra-wealthy himself, but he did all right—his salary was $180,000 and he had started picking up lucrative consulting gigs on the side. He’d recently started doing work for Gabe’s organization, Guarding Against Pandemics (GAP), which, backed by millions from Sam, was quickly becoming a powerhouse in Washington. One of Sean’s main jobs for GAP was to hype their work at every opportunity.

“This pizza is good,” someone said at the table.

“You know what else is good?” Sean said, looking at Gabe. “Pandemic prevention.” Subtle.

The conversation bounced around, from Democratic Senator Kyrsten Sinema’s habit of screwing up her party’s legislative agenda (Sean: “She has such bad politics, but she’s so hot”) to the question of whether Donald Trump would be president again (Sean: “He’s a cooked turkey”). There was talk, too, of the various recreational drugs used by different Democratic operatives (apparently Ecstasy was a popular choice for one well-known data guru). No one here was a particularly serious poker player. They bought in for $100 and bluffed when bored. Sean, especially, was prone to wild swings in chip count.

But Sean’s biggest wagers had nothing to do with cards. They had to do with politics. Tonight, Sean had his eye on the upcoming Democratic primary in Ohio, where Shontel Brown, the establishment choice running with the backing of the Congressional Black Caucus, was up against Nina Turner, the former Bernie Sanders campaign staffer and progressive-wing favorite who once compared voting for Biden to eating “a bowl of shit.” Political observers had been watching this race closely, since the outcome might hint at whether Democratic voters wanted to lurch left as the 2022 midterms approached (Turner) or stay the course (Brown).

Sean was betting it would be the latter. Literally. He had placed bets online and stood to win nearly $14,000 if Shontel Brown won.

“I make a lot of bets that would make progressives cry,” Sean said.

“How many active bets would you say you have right now?” someone asked.

“My inbox is so full of bets,” Sean said, “I don’t even remember what I have money on.”

“Do you make bets on races you’re working?”

The question lingered as the players seemed to mull the ethical implications. Betting on politics while working in politics, betting on clients? Was this normal? Should it be?

After a few seconds, Sean laughed.

“Who can say?” he said.

What is normal?

That was a common question after four years of Donald Trump in Washington. “This is not normal,” people would say when the leader of the free world raged at his own Justice Department, or undermined civil servants, or appeased bigots, or winked at conspiracy theorists, or palled around with geopolitical adversaries, or profited from his office, or told the American people blatant falsehoods over and over again. “Don’t normalize this,” admonished the admonishers. Nevertheless, Official Washington rearranged their habits around Trump’s personality. The opportunists went on television to lobby a president addicted to cable news. They sucked up to a praise-starved man in hopes of avoiding a “mean tweet” that could sink their business prospects or political aspirations. They wore ugly red hats and changed their opinions about free trade. Florida Governor Ron DeSantis was spotted moving his hands around during speeches—as if playing an invisible accordion—just like Trump did.

When Joe Biden ran for president, he offered a selling point that was rare for political campaigns: a return to business as usual. After he won, Washington residents cheered from their balconies and banged pots and pans and honked their car horns. It was a catharsis, Victory Day for normality. But the war wasn’t over. Two months later, Trump supporters led a violent siege of the U.S. Capitol to disrupt the peaceful transition of power. A coup attempt was thwarted, and Biden did assume his rightful office, but the odds of a return to normalcy were difficult to determine.

The future was a blind bet, and I spent the first year watching people place their wagers. I did interviews with President Biden’s Covid response team as they prepared to declare “independence” from the pandemic on July 4th, and then watched the Delta and Omicron variants keep that mission from being accomplished. I met retiring Democrat Representative John Yarmuth for an interview in his Capitol Hill office, and the Kentuckian described to me a recent argument on the House floor—between the progressive Mark Pocan, of Wisconsin, and the more moderate John Garamendi, of California—that he said nearly turned into a physical fight. (“John was basically telling Mark to get his head out of his ass,” Yarmuth explained to me.) Things were tense, he said. He drank a Dixie cup of whiskey during the interview; it was 2:30 p.m.

I watched Republicans take a step away from Trump after the insurrection, then watched them run back to him once they decided denouncing those lies was bad politics. I watched corporations stop donating to Trump allies who voted against certifying the election and then watched them start again. I heard MAGA diehards like Representative Marjorie Taylor Greene, the conspiracy theory fan turned bigoted blogger turned Georgia congresswoman, double down on the Trump election lies that had inspired the attack on the Capitol. I heard Dan Crenshaw, the Republican congressman from Texas, dismiss Greene as a performance artist who specialized in “self-inflicted controversy followed by claims of victimhood.”

“She lucked her way into Congress,” Crenshaw told me. “She says crazy things. And yet is looked up to. Why? What are we doing, guys?”

What some lawmakers were doing was trying to make federal legislation bipartisan again. The summer after Biden’s inauguration, Senator Chris Coons, the Delaware Democrat, told me about how a group of senators who were trying to wrap up an infrastructure bill had bonded as party guests on Joe Manchin’s houseboat, docked in a D.C. marina. Somebody else told me a story about Texas Senator Ted Cruz polishing off three beers in a matter of minutes while posing like Captain Morgan and chatting with a liberal colleague on Joe Manchin’s houseboat. Another person told me an anecdote about Alaska Senator Lisa Murkowski bursting into a chorus of “God Bless America” as she beheld the sight of the Washington skyline from the deck of Joe Manchin’s houseboat.

Senators schmoozing: That was normal, right? So was intraparty jousting: Manchin eventually helped sink Build Back Better, the huge bill that Biden hoped would guide his progressive agenda through Congress. Meanwhile, there was a lot of hand-wringing about Biden’s diminishing poll numbers and his advancing age. Trump and his lies had not gone away. Neither had the coronavirus. The pandemic had knocked the supply chain out of whack. Inflation was on the rise. For all his year-one wins—pandemic relief money, infrastructure, judicial appointments—Biden had failed to make things normal again. Even those who hadn’t soured on him began to wonder whether it might be time to consider an alternative candidate for 2024, especially with Trump lying in wait to retake the White House.

In February 2022, I walked into the White House to talk to Jen Psaki, then Biden’s press secretary. She had no reason to believe Biden wouldn’t run again, she said. And yet it had been a topic of conversation in her own home.

Her brother-in-law had come over for dinner recently, and Psaki had joked that she hoped there was a secret meeting happening “in a basement somewhere” to figure out a plan in case Biden didn’t run, she told me.

“And he looked at me,” she said, “and was like, ‘Should we be having that meeting now?’”

I was rarely the kind of reporter who chased The Big Story. I was more interested in the sideshow. When I started covering politics in Washington in 2010—first for National Journal magazine and later for the Washington Post—my job included writing about weirdos. People like Senator Jim Inhofe, the Oklahoma Republican and octogenarian climate change denier who forced me to consider my own mortality when he took me for a spin on his tiny airplane. And Brett Talley, a Republican speechwriter, who dabbled in paranormal detective work and took me ghost hunting in a cemetery near Georgetown. And Stephen Bassett, a registered lobbyist who represented UFO abductees.

When Trump descended from a golden escalator and became a candidate for president, he was just a sideshow. In fact, the Post didn’t plan to send a reporter to cover his announcement in person. I lobbied to be there—I was the sideshow guy. It was quickly becoming clear, however, that the sideshow was moving onto the main stage. With Trump in the White House, it was boom time for weirdness in Washington. The president suggested nuking a hurricane. He said of Kim Jong-un, the dictator of North Korea’s nuclear hermit kingdom: “He wrote me beautiful letters. And they’re great letters. We fell in love.” The coronavirus came and the president mused about injecting disinfectant and bringing light into the body. I reported a story about whether a recovered crack addict known as The MyPillow Guy represented the future of the GOP. Before it was over, a man dressed like a Viking would enter the chamber of the U.S. Senate.

Yes, Washington felt different under Trump. But what about once he left? Who was allowed to become powerful, and from where would they draw that power? What were the rules of the game, and how did you win? That’s a big part of what this book is about. It’s about the Washington that predated Trump, and the Washington he left in his wake.

Mostly, though, it’s about people.

I wanted to explore these questions by spending time with people who were trying to make post-Trump Washington work for them. I wasn’t as interested in the politicians themselves (boring, busy, overexposed) as much as the people whispering in their ears, or trying to. People like Sean McElwee.

Sean seemed to me like a type of person made specifically for Washington after Trump (brash, ideologically malleable, an outsider who wormed his way inside), while also being a type of creature that had swum this swamp for eons (brash, ideologically malleable, an outsider who wormed his way inside). He made big bets, big allies, and big enemies. He walked right up to the line of acceptable behavior, and kept walking. At my second poker night at his house, Sean showed off a new pair of pink high-tops he had bought with the money he’d made betting against Nina Turner’s primary campaign.

“I was polling for Nina Turner’s super PAC,” he announced to the table. “So I knew Shontel Brown was going to win.”

I couldn’t believe he’d just admit that. Even Pete Rose had the good sense to pretend he didn’t bet on baseball. What was even more surprising to me than the gambling was that, at the poker table, nobody seemed to think it was a big deal. By then it had already become clear to me that Sean was destined either to become the biggest thing in Democratic politics or to completely flame out. Because it was Washington, I also had to consider the possibility that both those things would happen.

Washington is a weird place like that, even in normal times—a place of change agents and stalwarts, strivers and survivors, wonks and wannabes, hustlers and true believers. Over the course of two years, I talked to as many of them as I could—an heiress to an oil fortune who got her start in politics at Occupy Wall Street; a cowboy diplomat who made his fortune as a fixer for foreign governments; the Republican shape-shifter who shifted his shape to thrive in Trump’s Washington; and the exiled Republican spokesman who eventually decided he couldn’t do the same. I talked to people working on Capitol Hill who were trying to figure out if Washington was the right place to be if they wanted to repair the country. I talked to a guy who left in order to repair himself.

In the course of reporting on their lives, I thought about how strange it was that they all ended up in the same city. They seemed so different. But in an important way they were similar: Politics was personal for them. The drama with their friends, the balance on their bank statements, the speeches they hoped people would give at their funerals, and the country they hoped to pass on to their kids—all were tied up in the livelihoods they had chosen for themselves.

America had gone through a big break, and in Washington people were sorting through the pieces—trying to put something together, or to keep something together. They were placing bets on the future, and hoping things would break their way.