The Teen Who Thwarted Bill de Blasio’s Presidential Announcement

How Gabe Fleisher, a high-school junior in St. Louis, got the scoop that forced the New York City mayor’s campaign team to rejigger its strategy.

There are three types of Presidential candidate. The first announces a bid for office in the morning, as Kamala Harris did when she declared her candidacy during the 7 a.m. slot of “Good Morning America.” The second announces at night: Kirsten Gillibrand spilled the beans to Stephen Colbert on “The Late Show” at 11:35 p.m. The third type is Bill de Blasio.

De Blasio wanted to be Type 1. Like Harris (and John Hickenlooper and Seth Moulton), he planned to announce his run on “Good Morning America.” His campaign video would air, and George Stephanopoulos would interview him. He wouldn’t earn any millennial cred for doing it that way, and he’d be passing up an opportunity to one-up Gillibrand, his fellow New Yorker, by appearing on James Corden’s show. But if he announced in the morning he could potentially dominate the day’s news cycle.

The day before de Blasio’s announcement, Gabe Fleisher, a junior at John Burroughs School, in St. Louis (prom theme: the jungle), was taking a four-hour A.P. English exam. “We didn’t have classes because of the test,” he said, over the phone, “and then we had a little health presentation on drugs and alcohol.” He got home from school earlier than usual, so he went up to his bedroom—framed copies of the Declaration of Independence and the Constitution, bumper stickers for Carly Fiorina and Frank Underwood—and opened up his Lenovo laptop to read some political blogs.

Since 2011, when he was nine, he’s written a newsletter called Wake Up to Politics, which has around fifty thousand subscribers. “I’m in St. Louis, which creates some barriers,” he said, “but anytime the story comes to me I’m always there.” (He looks up to the Times’ Maggie Haberman, another political journalist who lives outside D.C.) Fleisher has covered Donald Trump, Joe Biden, Mike Pence, Jeff Sessions, Bernie Sanders, and both Clintons during their visits to St. Louis. In March, he interviewed Nancy Pelosi. “A lot of the time at these events, I’m one of the few reporters who’s there, and so I’ve been able to set the scene, and offer really rich reporting,” he said. In 2016, when Jill Stein held a campaign event in St. Louis, Fleisher was one of two journalists who showed up. He published a long, exclusive interview with her. He was fourteen.

Last Wednesday, after the A.P. exam, Fleisher stumbled upon a Facebook event posted by the Woodbury County Democratic Party, in Iowa: “Join Mayor of New York City, Bill di Blasio [sic] on Friday, May 17 at 7:00 pm at 310 Virginia Street. (Next to Jitters.) Sioux City is his first stop on his Presidential announcement tour.”

“He hadn’t yet announced a Presidential campaign, so that definitely rang some alarm bells for me,” Fleisher said. “I reached out to both the county Party in Iowa and the de Blasio campaign to try and get confirmation of his Presidential bid.” When Fleisher posted a screenshot of the event notice on Twitter, retweets began to roll in, and media outlets picked up the story. The county Party deleted the event, misspelled name and all.

The de Blasio campaign had given news organizations a heads-up about the Mayor’s Iowa travels, but the information was under a press embargo. Within an hour of Fleisher’s scoop, news outlets broke the embargo and confirmed that de Blasio would formally announce his bid the next day.

The following morning, Fleisher’s alarm went off at 5:55 a.m. He started writing his newsletter. “I’m Gabe Fleisher, reporting live from WUTP World HQ in my bedroom,” he typed. “It’s Thursday, May 16, 2019. 263 days until the 2020 Iowa caucuses. 537 days until Election Day 2020.” A few minutes later, de Blasio’s campaign video dropped, showing the Mayor being chauffeured around the city in a black S.U.V., to a soundtrack of horn-heavy jazz. Meanwhile, on “Good Morning America,” Stephanopoulos read de Blasio the results of a recent poll: seventy-six per cent of New York City voters felt that he shouldn’t run. Outside the studio, protesters—who, thanks to Fleisher, had got wind of the Mayor’s announcement the night before—began to gather. (De Blasio’s run has unified the city: that morning, protesters from the New York Police Department and the Black Lives Matter movement stood together, chanting “Liar!”)

“Presidential announcements are so orchestrated to the minute,” Fleisher said. “I don’t think my tweet will change the trajectory of de Blasio’s campaign, but it fits very neatly into the narrative that this campaign is not destined to go very far.” He went on, “The fact that the state Party in Iowa clumsily put it out early, and his name was misspelled in the release, combined with the fact that journalists don’t see him as much of a factor in the race”—none of that bodes well. “I guess we’ll see whether that’s a narrative he can rebound from.” Then Fleisher laced up his gray Nikes and left for school. He had an oral presentation in Spanish to prepare for, and in his history class they were reading “Between the World and Me.” Later, for dinner, burgers. ♦