Sean McElwee, a young Democratic insider with friends in high places, bet on himself in the post-Trump era. But that wasn’t all he was betting on.
April 26, 2023 at 5:00 a.m. EDT
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!”
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?”
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.
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 circumst
