Somehow, Donald Trump did what no one else could do: annoy Taylor Swift enough to finally say something about this year’s presidential race. On Tuesday, after the presidential debate between Trump and Kamala Harris had finished, Swift released a statement giving her endorsement to Harris and, as a byproduct, gave Trump what is probably one of the more annoying nights of his life.
In her endorsement, Swift addressed the grotesque AI-generated images that Trump himself shared two weeks ago, which falsely depicted her as a clownishly tarted-up Uncle Sam, and her fans as Trump supporters. “It really conjured up my fears around AI, and the dangers of spreading misinformation. It brought me to the conclusion that I need to be very transparent about my actual plans for this election as a voter,” she wrote, signing off as “childless cat lady”.
For all the criticism of her silence up to this point, the signs were there. Swift has dipped her toes into politics in the past: in 2018, she used Instagram to endorse Tennessee’s Democrats in a senate race against the Republican candidate Marsha Blackburn, whose voting record on women’s and LBGTQ issues Swift disagreed with. Still, speaking out wasn’t a choice she made lightly: the Netflix documentary Miss Americana captured Swift’s agonising over possibly alienating a big chunk of her fans in Tennessee, her home state, who had stuck with her since she was a tween singing country music. “These aren’t your dad’s Republicans,” Swift told the cameras. “I need to be on the right side of history.”
“In the past I’ve been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now,” she wrote in 2018 – which was about Blackburn, but also very clearly about Trump, who responded petulantly: “Let’s just say I like her music about 25% less now.”
But by 2020, Swift was far less reluctant. Her lyrics were more overtly left-leaning: pro-choice, pro-LGBTQ, anti-racism and anti-sexism. She endorsed Joe Biden and Harris’ election bid in a Vogue interview. She also accused Trump of “stoking the fires of white supremacy and racism your entire presidency” in a tweet that was described as “The Tweet That Could Help Take Down A President”. Trump was out six months later.
Her endorsement of Biden annoyed Trump no end. “Why would she endorse this dope?” Trump reportedly said just this year. He recently complained online that Swift had chosen “the worst and most corrupt President in the History of our Country” (creative decisions about capitals all his).
There is a beautiful symmetry to Swift and Trump’s relationship: her naked dislike of him, and his desperation for her approval. In August, Trump shared a fake news article that falsely claimed her fans were “turning to Trump” after the foiled terror plot targeting her concerts in Vienna. While Swift’s politics undeniably overlap with Harris – on Tuesday, she praised Harris’ record “fight[ing] for the rights and causes I believe need a warrior to champion them” – it was Trump who chipped away at her inscrutable veneer.
The funniest thing in all of this is that Trump clearly likes Swift. She is everything he admires: rich, beautiful, famous and very good at doing business. She has her roots in country music, historically the preserve of conservatives. (Most of Trump’s celebrity endorsements have been male country singers: Jason Aldean, Kid Rock, Lee Greenwood.) When asked by journalist Ramin Setoodeh if he liked her music, Trump said: “Don’t know it well, but she is liberal, or is that just an act?” When told it wasn’t an act, Trump said: “It surprises me, you know. It surprises me. It surprises me that a country star can be successful being liberal.”
Setoodeh later described Trump as being “absolutely fixated” on her, saying that Trump thinks Swift “secretly likes him because I think it’s too hard for Donald Trump to accept the fact that someone who is so famous and has such a huge platform would not support his candidacy … even Donald Trump knows the value of an endorsement from Taylor Swift.”
And now, her endorsement has gone to his opponent. Last month, it was briefly rumoured that she would endorse Harris on stage at the Democratic National Convention, but even Harris’ people shut that down. An anonymous “DNC insider” gave this astonishing statement to Deadline: “Everybody loves Taylor, but having her here would overshadow everything. Think about it, no one would remember a word [Harris] said in her acceptance speech. All the headlines would be about Swift.”
So why wouldn’t Swift endorse Harris? She can’t be touched. She has nothing to lose. By many metrics, she’s the most powerful musician who has ever lived – and, as that anonymous insider worried, more powerful, in her own way, than would-be US presidents.
