Jack Sweeney: Troll? Stalker? Or Free Speech Hero?

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Two months ago, on December 22, Jack Sweeney, 21, was at a football game for his school, University of Central Florida, in Orlando. The college junior was trying to relax and have fun, but the Taylor Swift songs being blasted through the stadium speakers between downs were making that difficult. 

Earlier that day, Swift’s lawyers had sent him a cease and desist letter, accusing him of “stalking and harassing behavior,” and “direct and irreparable harm, as well as emotional and physical distress.” 

At the game, “I was thinking, ‘Did I seriously receive a letter from this person?’ ” Sweeney recalls to me over the phone. 

The computer science major had found himself in the crosshairs of Swift’s lawyers for social media accounts he managed that tracked the superstar’s private jet in real time. Two hours later, Sweeney says, his Instagram account @taylorswiftjets—there’s another account on Twitter, but it’s on a 24-hour delay—was suspended. 

Sweeney wasn’t just keeping track of Swift. Between classes, he runs an empire of social media accounts that chronicle the crisscrossing of some of the most famous people alive—from the Kardashians to Jeff Bezos and Jay-Z—via their private jets. 

Last month, Sweeney’s pro bono lawyers, provided by a civil liberties nonprofit, responded to the letter on his behalf claiming there was “nothing unlawful” about the account and that @taylorswiftjets was merely “engaged in protected speech.” 

The same week, Swift’s stalker, David Crowe, was arrested outside her Tribeca townhouse for the third time in five days. Whether the actions of people like Crowe can be linked to accounts like Sweeney’s is debatable, though certain public figures clearly think they are. 

When he first bought Twitter, Elon Musk held up his willingness to allow Sweeney to operate @Elonjets on the site as evidence of his commitment to free speech. That changed in December 2022, when a Tesla carrying Musk’s two-year-old son was attacked in L.A. (A day earlier, Sweeney reported that Musk’s jet had landed in the city.) Musk tweeted that the account would be suspended after all, and Sweeney would face legal action for bringing “harm to my family.” Earlier this month, Musk, who never brought legal action against Sweeney, posted on X that Sweeney is an “awful human being” and that Swift “is right to be concerned.”

“I was a big fan of his,” says Sweeney when I talk to him over the phone. Now, “He really hates me, obviously.” 

If Sweeney’s accounts pose thorny questions surrounding celebrity, privacy, free speech, and data in the internet age, he wasn’t looking to get into all that when he set them up in June 2020 as a senior in high school. He grew up a computer geek and his dad worked in operations at American Airlines. Tracking celebrity jets combined two of his fascinations: tech and aviation. A longtime Elon fan, he started tracking the CEO via a program he created with data from Elon’s jet’s transponder, a radio communication device that all planes are required to use.

FAA databases, government records, paparazzi shots from the tarmac, requests through the Freedom of Information Act, and a network of aviation geeks who track planes’ radio signals all help put the puzzle together. And Sweeney says he now has around 10,000 people who communicate via the messaging app Discord, helping him update spreadsheets keeping track of whose jet is whose.

“It’s really a journalism thing,” says Sweeney, pointing out that it’s in the public interest that, for example, a few days ago, Elon Musk, Ron DeSantis, and Donald Trump’s jets all landed at a West Palm Beach airport within a few hours of each other. “There must’ve been some kind of meeting,” speculates Sweeney. 

“I’m not trying to threaten them, which is what they’re saying,” he says. “A tool can be used in a good way or a bad way. I’m just putting the information out there.” 

Though the college junior, who travels by electric scooter—not a Gulfstream—has received some legal help, he tells me he has no real advisers. Mostly, he goes with his gut: when Elon Musk reached out in December 2021 offering Sweeney $5,000 to stop tracking his Gulfstream, he counteroffered $50,000, an internship, or a Tesla Model 3. But when Mark Cuban offered to be his friend if he’d retire the handle @MCubansJets, Sweeney said sure. “I’ve gotten basketball tickets from him a few times,” says Sweeney. 

Sweeney seems preternaturally relaxed that the planet’s biggest names in business and entertainment are ready to use their legal arsenals against him. “I have a screenshot from one of Taylor Swift’s fans messaging me saying they hope I get brutally murdered,” he deadpans. “I take it as it goes.” 

Suzy Weiss is a reporter and art director at The Free Press. Read more of her work here.

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