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Adapted from <a href="https://amzn.to/3Lvybha" target=_blank>“The Big Break: The Gamblers, Party Animals, and True Believers Trying to Win in Washington While America Loses Its Mind.”</a> ©2023 Ben Terris and reprinted by permission from Twelve Books/Hachette Book Group.

It was poker night at Sean McElwee’s Logan Circle bachelor pad. In the living room, a big‐screen television played “Rounders,” the 1998 Matt Damon movie. Extra‐large pizzas and cheap beer cluttered the counter in the kitchen, and tubs of protein powder sat on the shelves. A bunch of guys sat around a table: a spokesman for Facebook, a head of an organization attempting to end the filibuster, a former top aide to former Senate Majority Leader Harry M. Reid, a senior reporter who covered the Senate for MSNBC, and Gabe Bankman‐Fried, the brother and political confidant of the crypto billionaire Sam Bankman‐Fried.

They were Washington-insider types, people whose jobs brought them close to America’s political power centers. And Sean, their host?

“I’m in the business of making Joe Biden’s agenda look more popular than it really is,” he announced to the table, a few Miller High Lifes into the evening. “And business is booming!”

Twelve

It was July 2021. Biden’s presidency was six months old, his approval rating was hovering around 50 percent, and his agenda was on the move. McElwee, then 28 and the head of a Democratic polling group and think tank, was new to Washington 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, 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. Sean knew everyone, and 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.

Gabe Bankman-Fried, whose role involved helping his big brother figure out how to spend his money here in town, showed up semi-regularly to these poker nights. Gabe’s organization, Guarding Against Pandemics, was becoming a powerhouse in Washington, and Sean had been doing some work for them that involved hyping 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.”

Sean was not a subtle man. He was fond of saying things that seemed intended to get a rise out of people. He called himself a “Clarence Thomas Democrat” because, like the conservative Supreme Court justice, he advocated for more money in politics (which Sean thought would benefit Democrats). He called Lee Atwater, the infamous consultant who had helped Republicans win elections by being racist without appearing racist, his “political idol.” He once told me (in jest) that “no one understood the value of earned media” — a term for free press attention — “better than Osama bin Laden.” He walked right up to the line of what was acceptable, and kept walking. “I literally have a daily calendar alert that says: ‘Don’t put s--- in texts,’ ” I once overheard Sean say at a party. His general advice for staff, he joked, was that “it’s not illegal if you do it over the phone.”

No one around this table 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.

Washington is a town of gamblers, with members of the political class forever risking capital on candidates and movements, in the hope of scoring influence, money, status. In Sean’s case, political wagers were also literal.

Tonight he had his eye on the upcoming Democratic congressional 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.

Sean had placed wagers on an online prediction market and stood to win nearly $14,000 if Brown won.

“I make a lot of bets that would make progressives cry,” he 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. After a few seconds, Sean laughed. “Who can say?”

Bryan Anselm/Redux

Shortly after Donald Trump left Washington, I set out to write a book about the government town he had left behind. I spent two years getting to know an eclectic group of people who were trying to figure out how to make Official Washington’s new normal, whatever it was, work for them. There are those who would argue that chaotic presidency fundamentally changed the place, by remaking the rules of who could become influential. Others would say that the Trump years revealed Washington for what it had always been: a city filled with people who were willing to do what it took to get in the game.

Now that Trump was gone, who was allowed to buy in?

Sean seemed to me like a type of person made specifically for a post-Trump Washington (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). I figured that one way to understand politics after Trump was to try to understand how Sean ended up at this proverbial poker table — and watch to see whether he ended up winning big or going bust.

When I first met him in the summer of 2021, he was on a winning streak. Data for Progress, the nonprofit he had started three years earlier had grown to more than 20 employees, and helped Sean break into Washington’s power circles. He was on regular calls with Majority Leader Charles E. Schumer’s staff. He kept in contact with White House officials and some bigwig journalists on a group Slack channel. His polls were getting tweeted out by Ron Klain, Biden’s chief of staff. The organization’s work had been mentioned in private conversations by Biden himself.

Eventually Data For Progress would pick up a gig providing quick and cheap surveys for John Fetterman, who was running for Senate in Pennsylvania in what was shaping up to be biggest race of the 2022 midterms. And Sean would place a $3,000 bet that Fetterman would win his primary.

Sean was not shy about his gambling. He told people he bet $20,000 on Biden’s 2020 presidential campaign. He’d make prop bets with his buddies around the poker table. He’d sometimes end conference calls with other organizations by seeing if anyone wanted to make a wager with him about upcoming elections. He put tens of thousands of dollars a year on prediction markets, sometimes on contests as far‐flung as the Seattle mayoral race (“I won like $6,000 on that,” he told me). He once told me he would sometimes commission little polls “mostly” for the purpose of getting intel that he could use to make smart bets.

At that earlier poker night, Sean had demurred when one of his buddies asked if he ever bet on races he was working. But the next time he hosted a game, Sean showed off a pair of pink high‐tops he had bought with the money he’d made betting against Nina Turner, the more-liberal candidate in the Democratic Ohio primary. “I was polling for Nina Turner’s super PAC,” he announced to the table. “So I knew Shontel Brown was going to win.”

When I asked Sean if he worried his clients might read him as some kind of degenerate gambler, he said putting skin in the game forced a guy like him to be serious about his craft.

As the Biden era picked up speed, and Washington regained its muscle memory, it seemed clear to me that Sean was destined either to become the biggest thing in Democratic politics or to completely flame out. Either possibility seemed like a good bet.

Michael M. Santiago

Sean grew up in a religious and conservative family in Connecticut, became a libertarian intern for Reason magazine and the Fox Business Channel. Then he took a hard left turn and started working for a progressive think tank in New York and hosting happy hours at a dive bar in the East Village. For the most part, the weekly gatherings were just a bunch of lefty media personalities and a crew of gleefully vulgar Bernie Bros having their online arguments in real life, but Sean could come off as an operator. “He had a way of always looking over your shoulder for someone more important,” said Becca Schuh, a regular at the events.

There were, nonetheless, signs of genuine idealism in Sean. He had a girlfriend, Bobbi. Early in their courtship, she told me, they were hanging out in Sean’s bed when he decided to play her something from one of his Spotify playlists. It wasn’t mood music. It was a 1968 recording of Ted Kennedy’s famous eulogy at his brother Robert’s funeral — about how standing up for ideals, and working to improve other people’s lives, can create ripples of hope that combine to make a powerful current.

Bobbi grew to love Sean, and she was interested in pushing him to be the best version of himself. She would tell him when she thought he was playing too much online poker, which he seemed to be doing all the time, sometimes on multiple screens at once. She also suggested he should drink a little less booze and eat a little less takeout. She encouraged him to go to graduate school.

Sean didn’t stop gambling, but he did change. He went to Columbia University to get a master’s degree in social science and quantitative methods. He went all in on a weightlifting plan. He went from a “normal guy” who would play a lot of video games to someone who couldn’t stop talking about “discipline.”

By the time he moved to Washington part-time, Sean had tacked toward the center of the policy spectrum. This change was circumstantial. During the Trump years he became semifamous in Democratic circles for having popularized the slogan “Abolish ICE”— which wasn’t necessarily about getting the Immigration and Customs Enforcement agency abolished, but about expanding the leftmost limits of what Democratic policy goals could be seriously considered. Once Democrats controlled Washington, Sean thought it was time to get practical and pursue an agenda that was politically viable. This wasn’t so much a change of heart as a belief in using the instrument that worked with the current job at hand.

“The progressive movement is someone who spends every day hammering onto a nail,” Sean told me during one of our conversations, “and someone comes up and says, ‘You f---ing idiot, that’s a screw.’ ”

She works for Trump. He can’t stand him. This is life with Kellyanne and George Conway. (From 2018)

Data For Progress was his screwdriver. The organization’s strategy was at once simple and revolutionary: It was a polling business that would help drive media coverage about the popularity of progressive ideas. If Democrats needed some help figuring out which of their ideas were most popular, they could commission a poll from Sean’s organization for a fraction of the price of bigger shops.

“I think they are arguably the most influential Democratic pollsters in America,” David Shor, a prominent Democratic analyst and a friend of Sean’s, told me in October of 2022.

Bobbi later told me that she was proud that Sean had built an organization from nothing, and that he surrounded himself with a young, diverse staff. Still, looking back it was unclear to her whether Sean cared more about making the kind of change in the world Ted Kennedy talked about, or being rewarded with a Robert Kennedy-level eulogy once he left the world behind.

“It’s hard to tell,” she said, “the extent to which his belief in doing really good things is stronger than his belief in his own influence and going down in history as having done something important.”

Victor Llorente

On Nov. 2, 2021, Sean invited me to his apartment to meet his staff and watch returns come in from the Virginia governor’s race, where Democrat Terry McAuliffe was up against Republican Glenn Youngkin. A week earlier, Data For Progress had released a poll that showed McAuliffe winning by 5 percentage points. Sean was bullish on McAuliffe, and had wagered accordingly.

“If he wins by three, I break even,” he told me early in the evening, splayed out on his futon sofa, murdering zombies in a video game while I waited for his team to show up. “If it’s by two, I have a split loss, but that’s because if it’s over three, I’ll make $10,000.”

Sean encouraged his employees at Data for Progress to follow his lead when it came to betting on politics. He even held weekly wagering classes (his staff called him — half-mockingly — “Professor Sean”). These courses didn’t always involve real money, but Sean would sometimes Venmo members of his team small sums that they could use to place bets. “I do want my staff to gamble,” Sean told me. “People think it’s silly, but I actually think it’s very not silly. It is a really serious attempt to help them understand and engage with risk.”

The doorbell rang. In came Danielle Deiseroth, the team’s climate pollster; McKenzie Wilson, the communications director; Ethan Winter, lead analyst; and Marcela Mulholland, Data for Progress’s 25‐year‐old political director.

It wasn’t looking good for McAuliffe. Marcela was already nervous. “This morning you were telling me to put my freaking life savings on the line,” she said to Sean. “Am I f---ed? ” (Fortunately for Marcela, she had put only $10 on the race.)

When Marcela had landed a job at Data For Progress, her lefty friends held a dim view of her new boss. They thought Sean was a bandwagon guy, not a true believer. Marcela, who got into politics as an idealistic climate activist, worried he might be an “egomaniac.” And yet she found that Sean was great in the office — friendly, inclusive, encouraging. He had made a compelling case that the most progressive thing you could do was actually make progress. Marcela had grown to trust Sean and seek his approval. “Me and Sean are like BFFs,” she once told me. “He doesn’t have friends, but we’re friends. He’s an older person that I trust and I want him to feel proud of me.”

Like much of Data For Progress’s young staff, Marcela had never made a political bet until she started working for Sean. “Sean will say, ‘Gambling clears the mind,’” she told me. “And it really does. I really felt it. You get a rush.”

Jonathan Newton

Sitting with the crew that had shown up to his apartment, it sometimes felt like they talked like Sean when it came to the hammers and screws of Washington.

“I was on a call today with all these stupid f---ing progressives,” McKenzie said.

The call she had been on had been about a recent deal to lower prescription drug prices. It was a big achievement, but the progressives had compromised more than they wanted, and McKenzie — who had worked on Elizabeth Warren’s presidential campaign — had come to think of them as whiners.

“You just got a big f---ing win on prescription drugs, f---ing act like it,” McKenzie said. “It’s so stupid. No one ever wants to do a f---ing victory lap.”

There would be no victory lap for Terry McAuliffe on this night. The polls in Virginia had just closed, and it would be hours before anyone knew that Youngkin was going to win, or by how much (2 percentage points). Data for Progress missed on the polling, like pretty much everyone else.

But even before that picture came into focus, Sean’s staff were talking about what Democrats needed to do in the future. To achieve progressive things, they needed to at least appear to be moderate. If the fence-sitters thought the Democrats were a bunch of socialists, they would vote Republican.

“I definitely think I’ve become more moderate since working here,” said Danielle, who had worked on the 2020 Bernie Sanders presidential campaign.

“I look at so much data now that I’m like, ‘Huh, maybe this policy I really used to like isn’t as popular as I once thought,’” she continued. “I’m more pragmatic.”

“We drank the Kool‐Aid,” Marcela said.

Bryan Anselm

Sean and Bobbi broke up. She couldn’t handle his success, he told me, which made him think about whether she was someone he expected to spend the rest of his life with. He decided she wasn’t. “I’m not particularly emotional about it,” he said. “Or about anything, really.”

Their uncoupling, after seven years together, had been amicable. When I talked to Bobbi, some months after their breakup, it was Sean who gave me her number. She confirmed that Sean had not shed any tears when they split. “Homeboy does not cry,” she said. “I have seen it once, and I’m pretty sure it was fake.”

She wasn’t crushed by the breakup, either. Living with Sean, Bobbi had begun to have a difficult time feeling like her own person. “He really likes to influence the way people think,” she said. “It is really easy to get sucked up into that.”

They were still in touch; he had called her recently, she told me, and asked: “Am I an a--hole?”

Her answer was no. “A thing I will always respect and value about Sean is that he is interested in changing the world and using political power to make people’s lives better,” she told me. “And whatever ways he thinks is best, he will try.”

The second year of the Biden era dealt Sean some good and bad hands. John Fetterman suffered a stroke four days before his primary but won anyway. Sean won his $3,000 bet, and Fetterman’s campaign, happy with Data For Progress’s ability to churn out quick polls affirming their candidate’s popularity, kept them around for the general. Meanwhile, his breakup gave him an opportunity to play the dating market. “Me and David Shor are going to have a hot boy summer,” he said.

He wasn’t single long; Sean met a new woman, and fell in love. He attended a party at the White House to celebrate the signing of the Inflation Reduction Act, a signature Democratic spending bill that Data For Progress had worked to help pass.

Still, inflation remained high and Biden’s approval numbers had dipped since those booming days of summer 2021. As the midterm elections approached, things looked grim for the Democrats.

Caroline Gutman

One of the last poker nights I went to at Sean’s place was in September, less than two months before the midterms. Sean had bought a new, bigger, poker table; his game was growing. Tonight’s crowd included a chief of staff for a moderate House member, a pollster for a major Democratic polling outfit, and an assortment of think tankers. Sean was drinking a nonalcoholic Guinness — part of a recent lifestyle change that also had him eating plant‐based foods. This was how I learned that it wasn’t the booze that made him say whatever was on his mind.

“All of the Zoomers that work for me are bisexual, and all of them have long covid,” he said. “I’ll believe long covid is real when someone who is not bisexual has it.” (This was a joke. He later told a fact checker he didn’t even know the sexuality of his staff.)

The veganism was for health reasons but it also fit with a philosophy that he had been flirting with: effective altruism. Broadly speaking, proponents of effective altruism, “EA” for short, were obsessed with doing as much good as possible with every decision they made. Many of them had decided that cutting animal products out of their diets did more good for the world than harm to their own lives.

His attraction to EA made a certain amount of sense to the Washington version of Sean: It was a theory of goodness that was pragmatic.

Being part of the EA crew was also an effective way for Sean to pad his bank account — helping forge a connection with Sam Bankman‐Fried, the crypto billionaire, who was famously into the philosophy. Data for Progress did some polling for Guarding Against Pandemics, the organization run by Sam’s brother Gabe, but Sean had more to offer — separately — as a private consultant. He knew a lot of people in Washington. He could make introductions, and he could evangelize the hell out of Guarding Against Pandemics. “I’ve been paid a couple of times for my ability to bring things up at happy hours,” Sean once told me about his work for Gabe.

At one point in the night, Sean drew our attention to a little metal object he twirled between his thumb and forefinger. It was Sam Bankman‐Fried’s fidget spinner, Sean said, left behind after a recent visit by the billionaire.

Sean had been getting into crypto, too, by way of his gambling habit. He started using a site called Polymarket, which allowed gambling on elections. He told me and his poker buddies that he had used a virtual private network (a “VPN”) to hide the location of his computer, since Polymarket didn’t allow trading within the United States, and that he used the site to make bets on congressional races.

Less than a week before Election Day, Sean had invited me to a bakery around the corner from his office and told me he expected the Democrats to lose control of both chambers of Congress. Sean was placing his bets accordingly.

He opened up a spreadsheet of some of his bets with poker buddies. It was full of wagers against the Democratic candidates. “I think I’m going to make a lot of money on election night,” he said with a smirk.

In addition to betting against this party’s prospects in the House, Sean also had wagers against Democratic candidates in most of the competitive Senate races: Arizona, Nevada, Wisconsin, Ohio …

Then, there was the matter of Pennsylvania — and his own client, John Fetterman. The lingering effects from his stroke had contributed to a poor debate performance as his campaign hit the homestretch. Data For Progress’s recent polling showed the Democrat in decline, and Sean had sold his prediction-market shares on Fetterman’s general-election victory.

“I think he’s f---ed,” Sean said, taking a sip of his iced coffee.

“Do you own any Fetterman stock right now?” I asked.

“Let me see,” he said, checking his phone. “I have 53 shares on ‘No.’”

“Fifty‐three shares that Fetterman will lose?”

Political bets, like polls, are just a snapshot in time. Sean maintained he could always change his bets or dump all his stocks before Election Day. But in this moment, he was betting on his own client to lose.

“I think he’s at minus‐one or minus‐two,” he told me. “Once you go down, it’s really hard to see how you come back up.”

Ron Adar / SOPA Images

One week after the election, Sean McElwee walked through his neighborhood in the rain. His hair was wet and matted down on his forehead. The election had been a win, all things considered, for Democrats. They’d lost fewer seats than they’d expected in the House and, in large part thanks to the Fetterman campaign, held the Senate.

When I asked Sean about those shares he bought in a Fetterman loss, he claimed he’d dumped them at the last minute because he didn’t want to be on the “wrong side of that coin” going into Election Day. Still, the Fetterman people had heard a rumor (not from me) that Sean had been badmouthing their candidate’s chances. And they thought Sean had been preparing himself to look good in the event of a Republican wave by releasing a bunch of polls that looked bad for Democrats in swing states.

“I would love to apologize if you can find five minutes,” Sean had texted to Rebecca Katz, chief strategist for the Fetterman campaign, the day after the election.

Excellence in Feature Writing, Society for features Journalism

Brandeis University, B.A. in American Studies

Ben Terris is a writer in The Washington Post's Style section with a focus on national politics.

The Washington gambler