Donald Trump speaks during a campaign rally at the Expo World Market Center in Las Vegas, Nevada, on September 13, 2024.
PATRICK T. FALLON/AFP via Getty Images
From the moment Taylor Swift first spoke publicly about politics in 2018, the pop star has stood in opposition to Donald Trump — and the 45th president of the United States hasn’t kept quiet when it comes to her either.
Over the course of her evolution as a political advocate, Swift has done everything from call out Trump’s right-wing policies and incendiary language to urge her hundreds of millions of fans to vote against him in elections, with the “Blank Space” singer-songwriter more than once expressing regret over not doing more to prevent the politician from making it to the White House in 2016. Four years later, she promised Trump that the American people “will vote you out in November” after the then-president — whom she described as “stoking the fires of white supremacy and racism” — condemned the Black Lives Matter protests over George Floyd’s death.
As it turned out, Swift was right: Trump lost his re-election bid in 2020 to Joe Biden, who would initially run again in 2024 before dropping out of the race and passing the baton to his VP Kamala Harris. Through it all, the 14-time Grammy winner has remained steadfast in her resistance to Trump. Trump’s opinions on the musician, however, have been far less consistent, with the former president earning a reputation for praising Swift’s “unusually beautiful looks” one day and declaring his outright hatred of her the next.
From the pair’s early interactions long before either of them were politically involved to the heated criticisms they’ve lobbed at one another since, Swift and Trump go way back. Keep reading to see a timeline of everything the businessman-turned-president has ever said about the pop star below.
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Aug. 1, 2012: Thanks Taylor for a Picture
“@taylorswift13 Thanks for the beautiful picture— you are fantastic!” Trump tweeted Aug. 1, 2012.
It’s unclear where Trump and Swift might’ve snapped a picture together, and it doesn’t seem like that photo has ever seen the light of day. At this point, the businessman was nothing more than a wealthy reality TV star and mogul, while the singer — still making country music — was gearing up to release her album Red.
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Oct. 26, 2012: Reacts to Conor Kennedy Breakup
Trump appeared to weigh in on Swift’s breakup from Conor Kennedy in October 2012, tweeting, “Re: Taylor and Conor–great news for Taylor!”
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Oct. 30, 2012: Congratulates Taylor on Grammy Gig
Trump also took a moment in October 2012 to congratulate Swift on landing a major hosting gig with the Recording Academy that year. “Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5,” he tweeted. “Taylor is terrific!”
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Oct. 8, 2018: Says He Likes Taylor’s Music “25% Less”
After Swift broke her yearslong silence on politics ahead of the 2018 midterms, urging Tennessee followers to vote against Republican Marsha Blackburn — whom she’d later call “Trump in a wig” in her Miss Americana documentary — the then-president responded by saying the pop star “doesn’t know anything about” Blackburn, who later won her senate race against Phil Bredesen.
“Let’s just say I like Taylor’s music about 25% less now, okay?” he added at the time, speaking to White House reporters.
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Sept. 23, 2023: Weighs In On Tayvis
When Swift started dating Kansas City Chiefs tight end Travis Kelce in the fall of 2023, everyone seemed to have an opinion on the matter — including Trump. “I wish the best for both of them,” he told Daily Caller when asked for his take. “I hope they enjoy their life, maybe together, maybe not — most likely not.”
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Nov. 2, 2023: Claims He “Beat Taylor Swift” on the Charts
After recording and releasing a song titled “Justice for All” with a group of men incarcerated for their involvement in the Jan. 6, 2021 attacks on the U.S. Capitol, Trump had some pretty lofty claims about the project’s success. “And when that came out it went to the number one song, it was beating everybody,” he said during a rally in Houston.
“It beat Taylor Swift, it beat Miley Cyrus, who was number one and two,” he continued. “They were number one and two, we knocked them off for a long time.”
Though his and the J6 Prison Choir’s song did debut at No. 1 on Billboard‘s Digital Song Sales chart, neither Swift nor Cyrus had been Nos. 1 or 2 on the ranking the week prior.
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Feb. 11, 2024: Says There’s “No Way” Taylor Could Endorse Joe Biden
Before Joe Biden dropped out of the 2024 presidential race, Trump took to Truth Social to explain why he thought Swift couldn’t possibly vote for the then-president’s re-election — even though she’d endorsed Biden four years prior.
“I signed and was responsible for the Music Modernization Act for Taylor Swift and all other Musical Artists,” Trump wrote his post. “Joe Biden didn’t do anything for Taylor, and never will. 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.”
“Besides that, I like her boyfriend, Travis, even though he may be a Liberal, and probably can’t stand me!” he added at the time.
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June 2024: Calls Taylor “Unusually Beautiful”
In the June 2024 book Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, Trump had high praise for Swift’s looks.
“I think she’s beautiful — very beautiful!” he says in a passage. “I find her very beautiful.”
“I think she’s liberal,” he added in conversation with Variety‘s Ramin Setoodeh, who wrote the book. “She probably doesn’t like Trump. I hear she’s very talented. I think she’s very beautiful, actually — unusually beautiful!”
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Aug. 18, 2024: Posts “Swifties for Trump” AI Images
Trump never had Swift’s endorsement in the 2024 election, but impressionable followers might’ve thought otherwise when the twice-impeached former POTUS shared AI-generated images on Truth Social painting the 14-time Grammy winner as a supporter of his campaign.
One image featured a group of people wearing “Swifties for Trump” T-shits with the message “Swifties Turning to Trump After ISIS Foiled Taylor Swift Concert,” a seeming reference to a terrorist plot that led to the cancellations of Swift’s Eras Tour concerts in Vienna that August. Another doctored photo showed the musician wearing a top hat reading, “Taylor Wants You to Vote For Donald Trump.”
“I accept!” Trump wrote of the faux endorsement on the platform.
Later, the politician justified the posts on The Evening Edit. “I didn’t generate them,” he said. “Somebody came out. They said, oh, look at this. These were all made up by other people. A.I. is always very dangerous in that way.”
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Sept. 11, 2024: Reacts to Taylor’s Endorsement of Kamala Harris
Shortly after Trump’s first debate with 2024 Democratic nominee Kamala Harris, Swift gave her highly anticipated endorsement of the VP on Instagram. The “Anti-Hero” singer also cited the Trump campaign’s previous use of AI images portraying her as a MAGA supporter as one of the main reasons she felt it necessary to speak out against the Republican candidate, writing, “The simplest way to combat misinformation is with the truth.”
In response, Trump said: “I was not a Taylor Swift fan. It was just a question of time … She’s a very liberal person, she seems to always endorse a Democrat and she’ll probably pay a price for it in the marketplace.”
The politician also attempted to redirect attention on the pop star’s friend Brittany Mahomes, who is married to Travis Kelce’s teammate Patrick Mahomes. “I like Brittany, I think Brittany’s great,” he said. “Brittany got a lot of news last week, she’s a big MAGA fan. That’s the one I like much better than Taylor Swift.”
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Sept. 15, 2024: Says He “Hates” Taylor
Seemingly incensed by the pop star’s endorsement of his opponent, Trump blew off some steam in an all-caps declaration on Truth Social. “I HATE TAYLOR SWIFT!” he wrote.