—Photo-Illustration by Chloe Dowling for TIME (Source Images: Yuki Iwamura—AP (2), Michael Nagle—Bloomberg/Getty Images, Mel Musto—Bloomberg/Getty Images)The candidates hoping to represent New York’s 12th Congressional District sat shoulder-to-shoulder in a wood-paneled room on the fifth floor of the New York Society for Ethical Culture, a white stone building just off Central Park. They squirmed in their seats as the temperature outside hit 95, waiting for an unscreened Q&A from the nicest no-nonsense crowd on the Upper West Side: members of the League of Women Voters. Jack Schlossberg, the grandson of President John F. Kennedy, stretched out his long legs and leaned away from State Assemblyman Micah Lasher, the veteran state legislator endorsed by outgoing Congressman Jerry Nadler. Assemblyman Alex Bores, the man at the center of an AI proxy war, gave a friendly fist bump to George Conway, the former Republican whose campaign in this Democratic primary has been fixated on impeaching President Donald Trump. Five other candidates vying for the job, including public health researcher Nina Schwalbe, sat up there too—relieved to finally be invited to a forum, unlucky to be running in one of the most crowded, chaotic, and colorful races of the cycle.“There definitely are a lot of storylines, and certainly, there’s a lot of drama,” says Lis Smith, a Democratic strategist who lives in the neighboring 10th Congressional District. “In a district like this, affordability, things like that, are not as top of mind for voters as, simply, who's gonna fight back against Donald Trump? If you look at their ads, they’re all doing that just in different ways.”Fitting all the threads in New York’s 12th Congressional District primary into one neat package is a bit like trying to capture this densely packed slice of Manhattan itself. The district encompasses Central Park, Midtown, the Broadway Theater District, and the Upper East and West Sides. It is home to twenty-somethings in Stuy Town and Murray Hill, Gen X and Gen Y Chelsea types, and med students and families in Kips Bay. It is among the wealthiest districts in the country, one of the oldest, and one of the most densely populated. And while it is reliably blue, it’s not uniformly progressive. Voters here narrowly backed Andrew Cuomo over Zohran Mamdani in the New York City mayoral race.“Think your Obama Democrats, your Mario Cuomo Democrats,” says Mike Corbett, a member of the Manhattan Democratic Club from the district, who supports Bores. “It’s the New York Times-reading, old-school, traditional liberal Democrats.”These neighborhoods haven’t had a primary this wide open since 1992. In 2022, redistricting forced longtime and now-retiring Congressman Nadler into a battle with former Rep. Carolyn Maloney, which Nadler won. That race became a test of the East Side versus the West Side, but this year’s contest—with Bores the only major candidate from the East—doesn’t feel as geographically divided.The most recent polling from Emerson College showed Lasher with a slight lead, followed by Bores, then Schlossberg, and then Conway, after months in which Schlossberg had narrowly led. The most important takeaway from that poll may be that 32% of voters are still undecided. The sprint to primary day on June 23 is a test of what an increasingly frustrated but highly engaged bloc of Democratic voters want.On a late May morning, Lasher walks into the City Diner on 90th Street and Broadway and greets the owner with a familiar wave. The corner eatery has become a secondary campaign headquarters for the bespectacled technocrat who grew up a few blocks uptown. Lasher is only 44, with three kids—15, 14, and 10—but in the context of a race with 33-year-old Schlossberg and 35-year-old Bores—and with his endorsements from the likes of Nadler and former Mayor Michael Bloomberg—he can come across as the elder statesman in the race.He probably would have coasted to election 10 years ago: boasting experience in state government, and boosted by the $5 million Bloomberg has pumped into an affiliated super PAC. But in a moment when voters are rejecting establishment candidates, Lasher has had to defend that experience and those New York machine ties.“I’ve demonstrated over many years the ability to push against the status quo and make change through the legislative process, and that’s the job we are all running for,” he told me over sunny-side-up eggs and cranberry juice. “We’re not running to be a TikTok star. We’re not running to be an MSNBC commentator. And we’re not running to head an AI regulatory agency.”Instead Lasher talks a lot about his résumé. He is leading the fight to allow New York to redraw its congressional lines in response to Texas’s unprecedented mid-decade redistricting. The state budget includes two pieces of legislation he worked on—one prohibiting warrantless arrests by ICE agents in certain locations, and another giving New York the right to hold federal officers accountable for civil-rights violations. He has ideas for how Congress can undo some of Trump’s actions over the last two years. Asked how he thinks House Democratic Leader Hakeem Jeffries has done, he declines to answer, reiterating that he thinks there are tools his party can use to push back harder on Trump, even in the minority.A win for Lasher would show that even in one of the most hyper-engaged pockets of the country, seasoned legislators can still come out on top. “The work of change is still work,” Lasher says. “You have to know what you’re doing. It’s not enough to simply say, ‘things are broken and I alone can fix it.’ That’s what Donald Trump said.”Lasher sums up the race in two words: “intensely substantive.” He believes that may help him in the long run. “He’s done this a long time, and he worked for Nadler, who I loved,” Lisa DiCaprio, a professor at NYU, said of Lasher after the forum earlier this month. Experience, she says, may be poo-pooed by younger people, “but the rest of us value it.”At another diner, two miles downtown and several hours later, Alex Bores is talking to me about the mailroom in his Upper East Side apartment building. It is surreal, he says, to see his neighbors’ mailslots overflowing with flyers bearing his face—some promoting him, others attacking him.The battle for NY-12 has become about much more than a single congressional seat. It is an early look at how Silicon Valley titans are trying to flex political power as the pressure for AI regulation grows nationwide. And by virtue of authoring some of the country’s toughest AI-safety legislation in the New York statehouse, Bores, once a little-known legislator, has become a national figurehead for AI-safety regulation. Starting in late 2025, Leading the Future, a super PAC funded by executives tied to OpenAI, Palantir and Andreessen Horowitz, has poured millions into attacks on Bores. Then Anthropic, which has branded itself as an AI company open to safety-focused regulations, spent money supporting him. The result has been a deluge across airwaves, mailboxes, and text messages. The tech magnates intended the avalanche of attack ads as a warning to other candidates, but Bores has benefited from the spotlight. “As Democrats cast around for villains, tech billionaires are right up there with Trump himself,” Smith, the Democratic strategist said. “Attacks against Bores gave him something every candidate wants proof of—which is that powerful interests are afraid of him.” Bores argued that with “so many twists and turns, and eight candidates, being the only candidate that Donald Trump’s megadonors are spending millions of dollars against has been quite clarifying for voters. I think this is a race not about the past 34 years, but about the challenges of today and what’s coming in the future.”Bores’ stance on AI is not all that different from some of his competitors’, and yet he’s become synonymous with one of the biggest issues on voters’ minds. The former Palantir employee says he resigned from the company over moral objections to its work with ICE. He often touts that he would be one of only three members of Congress with a computer science degree. While he wants to regulate AI, he says he also uses it daily—to prepare for forums and organize his schedule, for example. Last year he coded a version of Google Maps that included the schedule for the Roosevelt Island tram.Laura Quigg, a 65-year-old retiree and treasurer of the League of Women Voters, says she’s leaning toward Bores because of his focus on AI. She thought it would “bring something new to the table in Congress that we don’t have right now.” His opponents, especially Schlossberg, have pointed out that Bores is not only benefiting from Anthropic’s support but also ties to crypto billionaire Chris Larsen, whose super PAC has funneled $3.5 million into boosting him. Bores pushes back on the notion that he is in anyone’s pocket. The son of labor organizers, he has racked up the most labor endorsements in the race and says he’s for working people.Over a chocolate milkshake at the diner, he rattles off favorite district touchstones: he got married in Bryant Park, learned to ride a bike at Carl Schurz Park, grew up going to Lexington Candy Shop, and still loves trips to the Museum of Natural History. He has embraced some more whimsical campaign efforts to stand out, like a Summer House watch party and stroller meetups with his 9-month-old son.Asked to describe the race in a few words, he went with: “Let New Yorkers decide.” Then, a few minutes later, after we had moved on to another topic, he stopped.“Can I change it? ‘Who gets power.’ That’s better,” he said. “Sorry. The compression algorithm took a minute.”Jack Schlossberg—the son of Caroline Kennedy, grandson of JFK, and cousin of U.S. Secretary of Health and Human Services RFK Jr.—sums up the race with his own campaign slogan: “Believe in Something Again.”“In this district—we have the U.N. here, we have the Empire State Building, Times Square, Lincoln Center,” Schlossberg, 33, says in a phone interview. “Those are monuments to the past, to a time when people believed in America … Right now, we can’t believe anything our President says. People are lying, and no one has any faith in Congress or in the Democratic Party. I’m running because I’ll never stop believing in either … and I want the Democratic Party to get its confidence back.”It is a remarkably optimistic pitch for someone who rose to fame for satirical social media videos trolling U.S. politicians. Among his most viral moments: Putting on a wig pretending to be Melania Trump talking to Vladimir Putin, and a post in April 2025 asking, “True or false: Usha Vance is way hotter than Jackie O,” the latter of whom happens to be his grandmother. When Pope Francis died shortly after Vance visited the Vatican, Schlossberg posted, “Okay JD killed the pope.”For the past seven months, he has been trying to channel the quest for virality into a more substantive campaign. “I’m not poking fun at Democrats who care and are working hard—I’m simply holding up a mirror to people in power to show them they’re not getting it right,” he said. “The time is up for manners and for being scared to ruffle feathers. We’ve got to break the door down and do things differently.”Despite a February endorsement from former House Speaker Nancy Pelosi, Schlossberg’s biggest obstacle has been convincing voters he is serious. A recent New York Times story described a disorganized campaign marked by frequent turnover and a lack of focus. The first question at the forum went to him from a woman who pointedly asked whether he could explain what experience he had that would qualify him for Congress.The candidate ran through his résumé, but his voice, strained from campaigning, kept cracking. Schlossberg has degrees from Yale and Harvard. He worked briefly at the State Department while his mother was ambassador to Japan and then campaigned for the Biden-Harris ticket in 2024 as he built a social-media following in the millions.“No matter who gets elected, we’re all going to be freshmen,” he told the voter at the forum. “We’re all going to be small fish in a big pond. But no matter where I go in my life, I stick out pretty badly everywhere I go, and I think that’s a huge value in a member of Congress.”Schlossberg argues that the party is hemorrhaging young voters, a demographic he says he understands. In our conversation, he called his party “slow and weak and late and timid.”With about a month left in the race, he has grown more aggressive, calling out Lasher and Bores for missed votes in Albany and accusing them both of letting dark money infiltrate the race. He has also rolled out some more specific policy proposals, including a plan to extend free access to HIV prevention drugs PrEP and PEP, as he accuses his cousin of rolling back federal prevention dollars at HHS. Other proposals are aimed at supporting performing artists, an expanded child tax credit, and an upcoming proposal he said will focus on e-bike safety. He has set himself apart as the candidate most opposed to U.S. funding for Israeli arms—a position that has evolved since the War in Iran started. Schlossberg now says he supports a bill authored by Senator Bernie Sanders designed to block nearly $660 million in U.S. offensive weapons sales to Israel. Lasher, Conway, and Bores have not said they would support that bill. The district is one of the most Jewish in the country, with Jewish adults making up approximately 20% of the electorate.In a race with a lot of policy agreements, Schlossberg also differs from his competitors in two other areas: He opposes a blanket moratorium on data centers and does not support mid-decade redistricting.“I think sometimes people don’t think they’ll like the taste of something until they try it for the first time,” Schlossberg says of his campaign. “Someone’s got to cook up a new recipe. I can elevate the profile of issues just by addressing them, and I don’t have to pander, because I was born with a platform—and built one myself—and I want to use both to elevate our public discourse.”George Conway held up the New York Times front page and gestured to a story about Trump’s proposed $1.8 billion “Anti-Weaponization Fund,” a pool of taxpayer payouts the Justice Department could disperse to redress claims from those who say they were prosecuted for political reasons. (The administration has since walked the plan back following a federal judge’s ruling blocking the fund and rare pushback from Republicans in Congress). “We are getting used to this,” he told the audience at the Ethical Society of Trump’s executive actions. “That’s the problem. I’m running because we need to put an end to it as soon as possible,” he said. “It has to be Job One: impeachment and removal of the President of the United States, his Vice President and the Cabinet.”Conway, 62, is a constitutional lawyer and Republican turned harsh Trump critic. In the 90s he was involved in Republican efforts to impeach President Bill Clinton over the Monica Lewinsky scandal. His ex-wife, Kellyanne Conway, worked on Trump’s campaign in 2016 and then on his White House staff. In 2019, George Conway co-founded the anti-Trump Lincoln Project. In late 2025, he registered as a Democrat, moved to Manhattan, and launched his run for Congress. He splits time between his apartment in Chelsea and spending time with his girlfriend who lives near Lincoln Center. Conway described the race as “unpredictable and wild.” His campaign can certainly contribute to that. Last week he recorded a podcast conversation with JoJo from Jerz, a prominent liberal political commentator, who made an erection joke as the two discussed the president’s penchant for constructing monuments in his honor. Conway made two campaign appearances at the Epstein Reading Room, an installation in Tribeca, where he walked among more than 3,000 volumes of the bound files, some 3.5 million pages stacked in bookshelves floor to ceiling.The room is more exhibit than actual library; visitors can’t manually go through the files. It’s about trolling Trump, which aligns with Conway’s mission. He has said he’d serve a max of two terms, one to argue the impeachment case against Trump and another to clean up the damage he believes the president has done. “Maybe some people don’t think it’s the winning strategy, but it’s the right strategy,” he tells me in a phone call. “I think any other approach isn’t really being realistic … You can have all the legislative proposals in the world in the next couple years, and you can have a Democratic majority, and the fact of the matter is you’re not gonna get these proposals past Donald Trump.”Of the top four candidates, Conway’s path to victory appears the most precarious. But he says he’s hopeful that undecided voters ultimately go with the person who they think will be most focused on fighting the president.“We have faith we’ll get a lot more votes than people think,” he says. “I just don’t think this is an era where talking points or policy points are gonna cut it.”