I Faced Down Taylor Swift’s Legal Wrath—And Won

How a mouse might feel going up against Godzilla is, I imagine, how Jack Sweeney feels right now. Sweeney, a third-year college student at the University of Central Florida, received a cease-and-desist letter from pop star Taylor Swift’s legal team in December.

Sweeney came into the crosshairs of Swift’s attorney because of his penchant for mining publicly available air traffic data and using it to track various celebrities’ private jets, then posting that information on public social media accounts. Swift, evidently, did not like this trick. And now they have bad blood, to say the least.

As someone who got the same treatment from Tay-Tay: Jack, welcome to the club. You’re not alone. And Taylor’s favored legal tactic, the cease-and-desist order, is a tired, hack tactic—not something to fear, typically.

Back in 2017, Swift sent a (legally farcical) cease-and-desist letter to me, too, over a blog post I wrote. She—or her legal team, rather—backed down after being publicly shamed by numerous bloggers and magazines. And once the smoke cleared, I have to admit that it kind of helped my career as an attorney.

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Let me explain. Back in 2017, I was a year post-law school, waiting for bar results and unsure of where my pending license and career would take me. I’d written a short piece of criticism of Taylor’s weird politics for a small blog, PopFront, I’d started with a few friends. Younger people might not remember this, but Taylor Swift used to be kind of apolitical. This seemed like a conscious PR strategy: Earlier in her career, she had more of a country flair to her, and likely did not want to alienate those right-leaning fans. I thought it was weird that so many alt-right types seemed to idolize her as an “Aryan” goddess, and equally weird that she didn’t seem like she was doing anything to stop them. So I wrote a blog about it under the headline “Swiftly to the alt-right: Taylor Swift subtly gets the lower case “kkk” in formation” and then forgot all about it.

Months later, when I received Taylor’s letter via email, I honestly did not think it was real. I figured there was no way that I could have possibly ended up on Taylor Swift’s radar. But somehow I did: Swift’s attorneys were out there trying to shut down tiny blogs like mine with only a few thousand readers a month.

But because of my law background, I knew that I had freedom of speech and thus had no reason to take down my blog article. And my first thought was to reach out to the American Civil Liberties Union, who agreed to represent me for free, and put out a sassy press release full of references to Swift’s songs.

“Not in her wildest dreams can Ms. Swift use copyright law to suppress this exposure of a threat to constitutionally protected speech,” ACLU attorney Matt Cagle wrote at the time. The media and the public loved it, and ate it up.

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The reason, I think, is that just about everyone identified with the David-versus-Goliath narrative. (Well, everyone except the Goliaths.) Interview requests pour in about the story, from CNN to Salon to Spin to Fox News (whom I turned down). I was hesitant to speak out at first, but I felt that commenting on the situation was part of fighting a greater injustice.

When I got my first job as an associate, the partners at my firm were impressed that I had the guts to go up against one of the most famous and influential people in the world to stand up for free speech. Later, a constitutional law professor asked me to give a guest lecture for her class.

I figured that the story would fade away, but online, it lingered. Likewise, other journalists and people in the entertainment industry reached out to me on Twitter with similar stories of receiving cease-and-desist letters, fearful of how it could change their lives or hurt their careers. After reading those stories, I felt even more strongly that the wealthy and powerful cannot get away with using lawyers to frighten and bully journalists.

There was one positive outcome from the whole saga: After Swift was roundly condemned for sending me that frivolous letter, she did start proclaiming her political stances and urging people to vote. I can’t see into Swift’s mind and know for sure whether I was the catalyst, but her political apathy was one of the points that I raised in my article.

Swift is one of the most-followed people on social media with a huge voice (and, until recently, carbon footprint). She can and should use her platform to push for social change, particularly given that she is a role model for many children and teens. It is unfortunate that she had to be shamed into taking a political stance, and that when given the opportunity for accountability and reflection, she chooses to go on the offensive with her legal team. I am not sure if these are truly her calls, but it reflects poorly on her and confirms her enormous levels of entitlement and privilege.

But back to Jack Sweeney. Admittedly, his situation is a little different from mine in that he’s no stranger to pissing off celebrities with his jet-tracking widgets. Previously, he infuriated Elon Musk by tracking his private jet as he zipped around the world. Musk then suspended him from X for that offense (and a new book suggests it may have been the catalyst for him to buy Twitter). But Swift, unlike Musk, doesn’t own any social media companies and cannot as easily hide someone else’s social media posts.

And finally, Sweeney should know that Swift has an odd penchant for writing songs about little details in her life—sometimes obscured through a few layers of analogy and metaphor. After being publicly harangued over her efforts to silence a mild-mannered blogger, Swift called her next album “Reputation.”

“My reputation’s never been worse,” she crooned on the single “Delicate.” I always wondered if the song, or the album, was maybe just a teensy bit about what happened with me or the ACLU. OK, probably not, but it’s something to laugh about, at least. And Sweeney might find himself asking the same question when there’s a song on Tortured Poets Department about her private jet.

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