Donald Trump’s Been Creeping on Taylor Swift Since She Was 22

Photo Illustration by Luis G. Rendon/The Daily Beast/Getty Images
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty Images

The year 2023 belonged to Taylor Swift, so naturally, the writer of a forthcoming book about Donald Trump and the history of The Apprentice made sure to ask the former president his opinion on the pop star when conducting an interview last November, Variety revealed on Monday.

“I think she’s beautiful—very beautiful! I find her very beautiful,” Trump tells author Ramin Setoodeh in Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass. “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!”

Trump has never been shy about his acute fascination with pop culture, taking time out of his busy schedule over the years to publicly weigh in on everything from Kristen Stewart’s relationship with Robert Pattinson to the infamous elevator fight between Jay-Z and Solange at the 2014 Met Gala.

But the recently convicted felon’s attempt to claim ignorance of Swift’s catalog is disingenuous: He’s nurtured a well-documented fixation on her over the years.

In August of 2012, in the midst of Swift’s country-pop Red era, Trump tagged the singer on X (formerly Twitter) and thanked her for “the beautiful picture.” However, if this tweet implies the existence of a photo of Swift and Trump posing together, it has almost certainly been scrubbed from the internet forever at the hands of Tree Paine, Swift’s formidable publicist.

“Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5,” Trump tweeted later that year. “Taylor is terrific!” Her later congratulated the pop star on her breakup from Conor Kennedy: “great news for Taylor!”

It’s only in more recent years that Trump has changed his tune on Swift. In 2018, Swift broke her previously uninterrupted streak of public silence on all matters even vaguely political when she posted on Instagram to express her opposition to Tennessee Senate candidate Marsha Blackburn, whom Trump had endorsed.

“I cannot vote for someone who will not be willing to fight for dignity for ALL Americans, no matter their skin color, gender or who they love,” Swift wrote.

Shortly afterward at a press conference, Trump smirked that he was “sure Taylor Swift has nothing, or doesn’t know anything about [Blackburn].” Then the infamous quote, later referenced on the Taylor Swift Netflix documentary Miss Americana: “And let’s say that I like Taylor’s music about 25 percent less now, OK?”

In Miss Americana, released in 2020, Swift calls Blackburn “Trump in a wig” in footage of conversations leading up to her decision to drop the post. When one of Swift’s entourage warns her that speaking out against the candidate will prompt the press to conclude that she is also condemning Trump, Swift makes her stance clear. “I don’t care if they write that,” she says. “I’m sad I didn’t say it two years ago.”

“I want to be on the right side of history,” she adds later.

In 2020, Swift endorsed Joe Biden for president and made her stance on Trump crystal clear. “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. @realdonaldtrump,” Swift tweeted.

“We do not want him as our president,” Swift added later, slamming Trump’s “ineffective leadership.”

Cut to January 2024, by which time many among the red-pilled far right had officially been driven mad by Swift’s mainstream omnipresence and especially by her frequent presence at boyfriend Travis Kelce’s NFL games.

Surely, they concluded, Swift must be a psyop for the FBI and the Pentagon, and her popularity had been inflated by Biden as a campaign strategy. Swift has yet to officially endorse any candidate in the 2024 election as of June, but both Trump and his supporters are already mad at what they fear would be a hit to his chances were she to weigh in once again.

Then, in February, Trump even went so far as to take credit for Swift’s financial success.

“I signed and was responsible for the Music Modernization Act for Taylor Swift and all other Musical Artists. Joe Biden didn’t do anything for Taylor, and never will,” Trump huffed on Truth Social.

“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,” Trump continued. “Besides that, I like her boyfriend, Travis, even though he may be a Liberal, and probably can’t stand me!”

Trump can whine all he wants, but he can’t refute hard evidence, like this video of the ex-president, his son Barron, and wife Melania Trump bumping “Blank Space” in their Rolls Royce. Sorry dude, you’re a fan.

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