At Crooked Media’s inaugural one-day event, Crooked Con, in Washington, D.C., Democratic U.S. Rep. Sarah McBride of Delaware took a viral moment during an appearance.
Appearing on the Friday morning panel “Flyover Country” at the Ronald Reagan Building and International Trade Center, McBride was asked about a comment she’d made weeks earlier — that Democrats have “sort of been assholes to voters.” Smiling at the mention, she leaned into the question rather than away from it.
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“It’s true,” McBride, the first out trans member of Congress, said. “Voters fundamentally ask two questions: Does this candidate like me? And what does this candidate think? If you can’t answer the first question, they never get to the second.”
She paused before adding, “You can’t build a diverse working class coalition if people don’t feel like you like them. And that means not being assholes to our base either.”
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The standing-room-only audience laughed as she then went further. “A big tent,” she said, pausing for effect, “is bisexual.” The laughter turned into cheers.
“That means it goes both ways,” she continued. “It starts with us being kind to one another, being respectful to one another, and being welcoming to one another.”
The one-day convention followed a surprise Thursday night appearance by former President Barack Obama at a live Pod Save America taping at the Warner Theatre. His unannounced cameo — his first alongside the podcast’s hosts in years — drew roaring applause and set the tone for Crooked Media’s first-ever convention: part reunion, part strategy summit, part rallying cry.
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By Friday morning, the Reagan Building was teeming with Crooked fans, content creators, volunteers, and Democratic leaders. Organizers estimated more than 3,000 people attended panels, live tapings, and workshops spread across three main stages. The event, created by Pod Save America hosts Jon Favreau, Jon Lovett, Dan Pfeifer, and Tommy Vietor, also served as a fundraiser through Vote Save America Action, supporting food banks and local aid groups that assist families affected by the government shutdown.
Moderated by former Obama White House deputy chief of staff Alyssa Mastromonaco, the “Flyover Country” panel explored how Democrats can reconnect with voters in states long considered unwinnable. Alongside McBride were Rep. Janelle Bynum of Oregon; Anderson Clayton, chair of the North Carolina Democratic Party; and Ben Wikler, former chair of the Wisconsin Democratic Party.
McBride’s point about Democrats needing to “like voters again” set the tone, but each panelist approached the question of connection differently.
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Anderson Clayton, 26, the youngest state party chair in the country, told the crowd that Democrats can’t keep writing off rural America.
“We’ve told people in these communities that the only way to succeed is to leave,” she said. “You can’t organize those you don’t love.”
She described driving across North Carolina’s 100 counties to talk with voters herself. “When people actually meet a Democrat, they realize we’re not the caricatures they see on Fox News,” she said.
Ben Wikler, who helped orchestrate Democrats’ state-level wins in Wisconsin, said the party’s best strategy is empowerment. “Have great candidates, energize people, and give them the realistic knowledge that they’re powerful,” he said. “Before Tuesday, there were 47 elections this year. Democrats have won or overperformed in 46 of them.”
Rep. Janelle Bynum, Oregon’s first Black member of Congress, offered a blunt reminder that hope alone doesn’t win elections.
“I’ve always had competitive districts,” she said. “That means discipline: call time, door-knocking, and accountability. Democracy isn’t optional.”
McBride returned repeatedly to the idea that curiosity and empathy must replace what she sees as a moral superiority within the party.
“We’ve started to treat relationships as tools to reward or punish people for being right or wrong on issues,” she said. “If everyone who loves trans people cuts off everyone who says the wrong thing, there’s no one left in those people’s lives to help them evolve.”
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Her argument — that persuasion is an act of hope, not compromise — echoed the event’s larger theme of reengagement. “Being in relationship with people doesn’t mean you agree with them,” she said. “It means you’re creating space for them to grow.”
During the session, McBride told the audience that change is vital to democracy. People and their politics change, she said, so it's important to give space for that. “Most people have goodness and decency in them. We can tap that if we stop assuming we already know who they are.”
Mastromonaco closed the session with a story about Obama’s approach to disagreement. During a disaster response trip, she said, he insisted on including a political rival. “He told me, ‘Lead with curiosity,’” she recalled. McBride nodded, calling curiosity “a political strategy as much as a virtue.”
After the panel, McBride expanded on her “big tent is bisexual” metaphor in an interview with The Advocate.
“The big tent goes both ways,” she said. “When we’re building a big tent to win, yes, it means welcoming people who are in the center or to the right of us. But it also means welcoming people who might be to the left. Too often, the center of our party has used purity politics to cancel or exclude progressives, and we have to reject that too.”
She said the lesson of Democrats’ recent win, including Virginia Gov.-elect Abigail Spanberger’s, is that authenticity, not orthodoxy, wins elections.
“When we hold true to our values and meet voters where they are, when we don’t stick our heads in the sand, we can neutralize attacks and win elections all at the same time,” she said. “Voters are seeing through the Republican Party’s hateful shtick. They see that it’s the GOP, not Democrats, that’s obsessed with culture wars, because they have no solutions to the affordability crisis.”
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