Everything He’s Said About Pop Star

“@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.

Trump appeared to weigh in on Swift’s breakup from Conor Kennedy in October 2012, tweeting, “Re: Taylor and Conor–great news for Taylor!”

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!”

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.

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.”

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.

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.

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!”

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-shirts 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.”

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.”

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.

Both Trump and Swift were in attendance at the 2025 Super Bowl, with the former becoming the first sitting president to ever attend the big game and the latter showing up to support Kelce during the Kansas City Chiefs’ match against the Philadelphia Eagles. At one point, some people in the crowd booed when the pop star’s face came on over the big screens — and the politician jumped at the chance to rub it in later that day.

“The only one that had a tougher night than the Kansas City Chiefs was Taylor Swift,” he posted on Truth Social. “She got BOOED out of the Stadium. MAGA is very unforgiving!”

When the Philadelphia Eagles visited the White House after defeating the Kansas City Chiefs in the February 2025 Super Bowl, the president couldn’t resist making a dig at Swift again. “It was an incredible game. A little surprising, but right from the beginning of the first quarter of the big game, which I was there I watched in person,” he said at the time. “I was there along with Taylor Swift, how did that work out? How did that one work out?”

Trump may have once declared the pop superstar to have “unusually beautiful looks,” but in a seemingly unprompted message on Truth Social, he appears to have changed his mind. “Has anyone noticed that, since I said ‘I HATE TAYLOR SWIFT,’ she’s no longer ‘HOT?’,” he wrote, unprovoked.

Trump took another shot at Swift while praising Sydney Sweeney in a lengthy Truth Social post, which came after the Euphoria star — who is a white woman with blonde hair and blue eyes — faced backlash for touting her “great genes” in an American Eagle ad campaign. While critics slammed the ads as being akin to Nazi propaganda, the president wrote, “Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there.”

He then compared Sweeney to Swift. “Just look at Woke singer Taylor Swift,” he wrote. “Ever since I alerted the world as to what she was by saying on TRUTH that I can’t stand her (HATE!) She was booed out of the Super Bowl and became, NO LONGER HOT. The tide has seriously turned — Being WOKE is for losers, being Republican is what you want to be. Thank you for your attention to this matter!”

Trump was alerted to the news of Taylor Swift and Travis Kelce’s engagement during a cabinet meeting. Asked for his reaction, he said, “I think he’s a great player, I think he’s a great guy, and I think that she’s a terrific person, so I wish them a lot of luck.”