Photo-Illustration: Intelligencer; Photos: Getty
Over the years, Donald Trump has repeatedly embarrassed himself by picking fights with musicians who are much cooler than he is, from John Legend to Rihanna. Now it seems Trump has learned his lesson a little too well. Rather than lashing out at Taylor Swift, Trump has taken the opposite approach: He keeps complimenting her publicly and suggesting she might endorse him in the 2024 election. This just makes Trump look pathetic, as it’s quite clear that she won’t.
The latest proof that Trump is in deep denial about his status as a Swift foe comes from the new book Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass. In a November 2023 interview with the author, Variety co-editor-in-chief Ramin Setoodeh, Trump was asked to share his thoughts on the Eras Tour artist.
He could have said something noncommittal. Instead, according to a book excerpt released by Variety, Trump gushed about how “beautiful” Swift is, which is the highest compliment he can think of for a woman:
Trump, usually one to punch back at critics, is smart enough to know Swift’s fame is on another level. “She’s got a great star quality,” Trump says. “She really does.” Trump is effusive as he uses one of his favorite adjectives to describe women — “beautiful” — several times in a row.
“I think she’s beautiful — very beautiful! I find her very beautiful. I think she’s liberal. She probably doesn’t like Trump. I hear she’s very talented. I think she’s very beautiful, actually — unusually beautiful!” It’s her fame, not her songcraft, that fascinates Trump. When asked about Swift’s music, played so frequently on the radio that it’s inescapable in daily life, he says, “Don’t know it well.”
Weeks later, CNN played the audio recording of what Trump said about Swift:
It is somewhat plausible that Trump doesn’t know much about Swift’s music. While there’s video of Trump driving around a listening to “Blank Space,” it doesn’t seem that Swift songs get much play when the former president is DJing at Mar-a-Lago. But Trump strained credulity when he suggested that as a “country star,” Swift might secretly be MAGA:
Beyond Swift’s looks, what intrigues Trump the most is the idea — frequently bandied about online before she endorsed the Democratic Senate candidate in Tennessee in 2018 — that she could secretly be supporting him. “But she is liberal, or is that just an act?” he asks me. “She’s legitimately liberal? It’s not an act? It surprises me that a country star can be successful being liberal.”
I tell Trump that Swift is no longer a country star; she’s been making pop music for years. He doesn’t seem aware of this, but he reaches for a different name. “Garth Brooks is liberal. Explain that! How does it happen? But he’s liberal.” Trump trails off. “It’s one of those things …”
No one should expect a 77-year-old show-tune lover to have his finger on the pulse of American pop music. But you’d think that Trump would remember how Swift repeatedly criticized him on Twitter in the lead up to the 2020 election and endorsed his opponent, Joe Biden, several months later:
The Swifties were not buying the idea that the star might secretly like Trump; the phrase “STAY AWAY FROM HER” trended on X on Monday, according to Newsweek. And Swift has given no signs that she might lean to the right. She released a whole documentary about her decision to speak out against GOP Tennessee Senate candidate Marsha Blackburn in the 2018 midterms, she’s continually spoken out in favor of LGBTQ rights, and the Eras Tour opens with the anti-Trump song “Miss Americana & the Heartbreak Prince.”
Whether Trump was actually ignorant of Swift’s political views or just playing dumb, he got up to speed within a matter of months. By January 2024, he was reportedly fretting about whether Swift was more popular than him and what might happen if she backs Biden again. And on Super Bowl Sunday, he practically begged Swift not to endorse Joe in a post on Truth Social:
Since Trump’s strategy for winning Swift over seems to entail calling her pretty, admitting he’s unfamiliar with her work, and taking credit for her financial success, Biden probably doesn’t have to worry about losing her endorsement.
This post has been updated to include audio of Trump’s remarks.
