Every Wild Thing Donald Trump Has Said About Taylor Swift

When Taylor Swift asks, "Who's afraid of little old me?" the answer might just be Donald Trump. The 45th U.S. president seems to be almost as obsessed with the "22" singer as he is with sharks, wind turbines, and Hannibal Lecter.

One of the occasions when Swift shared her political views was before the 2020 presidential election. When the "Speak Now" hitmaker decided to speak up that year, she not only endorsed Joe Biden but also blasted Trump amid the protests sparked by the murder of George Floyd. She was addressing the violent language Trump had used against the protesters when she tweeted, "After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence? 'When the looting starts the shooting starts'??? We will vote you out in November."

Swift's words had to wound Trump at least a tad, seeing as how he'd been a Swiftie for years by then. Back when he was still using X, formerly known as Twitter, to share his tortured poetry with the world, Trump expressed his admiration for Swift. In 2012, he fired a message her way that read, "Thanks for the beautiful picture— you are fantastic!" Just imagine the uproar there'd be if he dug that photo up and tried to use it in his campaign. Based on what else he's said about Swift over the years, there's only one logical conclusion: he loves her, and it's ruining his life.

Donald Trump has a reputation for being rude to reporters, but there are some breaches of decorum even he can't abide. He didn't like it one bit when Kanye West treated Taylor Swift like a debate rival by interrupting her at the 2009 MTV Video Music Awards.

Swift won the best female video award for "You Belong with Me," but Ye believed her Moonman trophy belonged with Beyoncé. "I'm really happy for you, Imma let you finish," the rapper told Swift after grabbing her mic. "But Beyoncé had one of the best videos of all time." The viral moment dominated the online discourse for a long while, and Trump was among the celebs who weighed in on it. Swift's knight in shining orange armor told TMZ he found Ye's behavior "disgusting," and he embraced cancel culture before it was even a thing by suggesting Ye needed to be boycotted. Trump also theorized that the "Heartless" singer's stunt had nothing to do with his appreciation for the "Single Ladies (Put a Ring on It)" music video. "He couldn't care less about Beyoncé. It was grandstanding to get attention," scoffed the man who cares not one whit about getting attention (*insert eye roll*).

In 2012, Trump made sure to let Swift know he'd be watching her on a different awards show. "Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5. Taylor is terrific!" he tweeted.

Some of the minor characters in the history of Donald Trump and Taylor Swift's mostly one-sided relationship have also played roles Trump's political career. Kanye West has expressed support for Trump, while Robert F. Kennedy Jr. became one of Trump's rivals in the 2024 presidential election. RFK Jr.'s connection to Swift is that she briefly dated his son, Conor Kennedy.

Swift and Conor's relationship began in 2012 and lasted around two months. During that time, Swift purchased a house not far from the Kennedy family's Cape Cod estate. In his book "The Kennedy Heirs: John, Caroline, and the New Generation — A Legacy of Tragedy and Triumph," author J. Randy Taraborrelli writes that Conor dumped Swift. "This business of her buying a house on the Cape made him nervous," a source close to Conor said. From the sounds of it, Swift found the idea of marrying into a political dynasty appealing. But Trump saw the end of their relationship as a positive development. "Re: Taylor and Conor–great news for Taylor!" he tweeted.

It's unclear what Trump had against Conor at the time, but Americans would learn that the ex-president's assessment of the situation was accurate when RFK Jr.'s 2024 presidential campaign became a PR nightmare. If Swift's relationship with Conor had continued progressing, she could have ended up with a father-in-law who confessed to dumping a dead bear cub he planned on eating in Central Park.

In 2014, Melania Trump provided proof that the Trumps used to be a Swiftie family. On her Facebook page, she shared a video of herself, Donald Trump, and their son Barron Trump cruising around in a Rolls-Royce while blasting "Blank Space." But four years later, Taylor Swift got on Trump's bad side by getting political in a way that didn't benefit him.

In what was an unprecedented action for her, Swift decided to make some political endorsements during the 2018 U.S. midterm elections. On Instagram, she revealed that she was voting for two Democratic candidates from Tennessee in the Senate and House races and explained why she would not be supporting Senator Marsha Blackburn. "She voted against the Reauthorization of the Violence Against Women Act, which attempts to protect women from domestic violence, stalking, and date rape," read one of Swift's complaints.

When Donald caught wind of Swift's post, he dismissed it by suggesting that the singer was misinformed about Blackburn, according to AP. However, Swift was right when she said in her post that Blackburn has fought against marriage equality for same-sex couples, and Politifact rated Swift's claim about Blackburn's Violence Against Women Act voting record "mostly true." Swift's post wasn't enough to keep the Senate seat out of Blackburn's grasp, and the entertainer lost some support from at least one of her fans. "Let's say that I like Taylor's music about 25 percent less now, OK?" Trump huffed.

Ahead of the 2024 Super Bowl, Donald Trump was hyper-focused on the same thing as everyone else in America: Taylor Swift and Travis Kelce's relationship. It didn't escape his attention that Swiftie fever was at an all-time high, which perhaps gave him unhappy flashbacks to that fateful moment in 2020 when Swift endorsed Joe Biden for president. This time around, Trump believed he had done something to earn Swift's favor.

Trump tried to accomplish many things in a pre-Super Bowl Truth Social post. He attempted to take credit for some of Swift's colossal net worth, fished for an endorsement, and took a swipe at a political foe. "I signed and was responsible for the Music Modernization Act for Taylor Swift and all other Musical Artists. ... There's no way she could endorse Crooked Joe Biden, the worst and most corrupt President in the History of our Country, and be disloyal to the man who made her so much money," he wrote. Dina LaPolt, an attorney who worked on the piece of legislation in question, told Variety that all Trump did was sign his name to a lot of other people's hard work. LaPolt further suggested that Trump likely has no clue how the Act functions.

Trump also tried to score some brownie points with Swift by complimenting her beau. "I like her boyfriend, Travis, even though he may be a Liberal, and probably can't stand me!" he wrote.

For Donald Trump, old habits die screaming. In 2024, he resumed gushing over Taylor Swift in an interview for the book "Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass." In an excerpt published by Variety, Trump speaks about Miss Americana as if she's a contestant in the Miss USA pageant he used to own. "I think she's beautiful — very beautiful! I find her very beautiful. ... I think she's very beautiful, actually — unusually beautiful!"

Amid all that praise for Swift's most superficial attributes, Trump did not admit that he likes her music. Instead, he said, "I think she's liberal. She probably doesn't like Trump. I hear she's very talented." So, even though he's outed himself as a fan in the past, he couldn't acknowledge this, likely because Swift has been so vocal in her disapproval of him. But to be fair, he seemingly quit following her career around the time she made the switch from country to mainstream music. "She is liberal, or is that just an act? She's legitimately liberal? ... It surprises me that a country star can be successful being liberal," he mused. So, Trump probably hasn't heard Swift sing about wanting to kill an unfaithful husband like himself in "Fortnite." Also, based on his difficulty believing that Swift leans to the left, he might be holding out hope that she'll someday switch her political affiliation like she switched genres.