Everything Donald Trump has ever said about Taylor Swift – from 'unusually beautiful' to 'I HATE HER'

Of all the reactions to Taylor Swift and Travis Kelce’s surprise engagement, one in particular left the internet doing a collective double take: Donald Trump’s.

The president – not one to hold back, especially when it comes to celebrities – kept things unusually civil when asked about the pop culture moment of the year, offering: "I wish them a lot of luck."

But for someone who’s previously called Swift "unusually beautiful," pushed fake AI-generated 'Swifties for Trump' posts, and later shouted (digitally) "I HATE TAYLOR SWIFT", the bizarre well-wish has fans wondering: since when?

Trump’s relationship with the global superstar has been bizarre, inconsistent, and at times downright aggressive.

So, as her engagement makes headlines, here's a look back at every time Donald Trump has publicly fixated on Taylor Swift – the compliments, the contradictions, and, of course, the all-caps rants.

August 2025: Engagement reaction

During a cabinet meeting on Tuesday (26 August), the president was asked about the "biggest pop culture news" happening right now: Taylor Swift and Travis Kelce's engagement.

When a reporter asked his reaction, Trump simply quipped: "I wish them a lot of luck."

He added: "I think it’s – 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."

Sydney Sweeney comparisons

On 4 August, Trump praised Euphoria star Sydney Sweeney following her American Eagle controversy and rumours that she's a Republican.

"Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there. It’s for American Eagle, and the jeans are 'flying off the shelves,'" he shared to Truth Social.

He also somehow managed to drag Swift's name into the mix, adding: "Or just look at Woke singer Taylor Swift. 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."

May 2025: 'No longer hot'

Once upon a time, Trump described Swift as having "unusually beautiful looks".

However, in a post on 16 May, he seemingly backtracked – and believed he caused her imaginary downfall.

"Has anyone noticed that, since I said ‘I HATE TAYLOR SWIFT,’ she’s no longer 'HOT?'" the president randomly wrote.

February 2025: Super Bowl dig

During the 2025 Super Bowl, Swift briefly appeared on screen – prompting some boos from the crowd. Trump wasted no time seizing the moment, quickly posting about it on Truth Social.

"The only one that had a tougher night than the Kansas City Chiefs was Taylor Swift," he shared. "She got BOOED out of the Stadium. MAGA is very unforgiving!"

September 2024: 'I HATE TAYLOR SWIFT!'

Clearly riled by the pop star’s support for his political rival, Trump took to Truth Social with an all-caps outburst: "I HATE TAYLOR SWIFT!"

In a separate instance after Swift shared her support for Kamala Harris on Instagram, Trump quipped: "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."

August 2024: Sharing AI-generated 'Swifties for Trump' pictures

Once again on Truth Social, Trump shared a series of photos showing supporters donning 'Swifties for Trump' T-shirts, making impressionable voters take a second look.

"I accept!" Trump wrote as the caption, though he later clarified that he didn't generate them.

He told The Evening Edit: "Somebody came out. They said, oh, look at this. These were all made up by other people. AI is always very dangerous in that way."

Truth Social

June 2024: 'Unusually beautiful'

Speaking about Swift in a passage in Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, he said: "I think she’s beautiful – very beautiful... I find her very beautiful."

"I think she’s liberal," it continued. "She probably doesn’t like Trump. I hear she’s very talented. I think she’s very beautiful, actually — unusually beautiful!"

February 2024: Trump convinced Swift wouldn't endorse Biden

Trump seemed convinced that Swift wouldn't endorse Joe Biden (who was originally the presidential candidate before dropping out in July).

“I signed and was responsible for the Music Modernization Act for Taylor Swift and all other musical artists,” Trump claimed on Truth Social.

“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.”

November 2023: 'Trump beat Swift in the charts'

Trump boldly claimed that 'Justice for All' – a track recorded by men imprisoned for their roles in the 6 January 2021 Capitol riot – had soared to the top of the charts, even outperforming Taylor Swift.

"And when that came out it went to the number one song, it was beating everybody," he said at a rally. "It beat Taylor Swift, it beat Miley Cyrus, who was number one and two. They were number one and two, we knocked them off for a long time."

October 2018: He likes Swift's music '25 per cent less'

When Swift endorsed Tennessee’s democratic Senate candidate Phil Bredesen in 2018, Trump was not happy.

In response, he told reporters: "Let’s say that I like Taylor’s music about 25 per cent less now, OK?"

October 2012: Trump's fan era

Back in 2012, before his pivot into politics, Trump was primarily recognised as a TV personality, largely thanks to his role on The Apprentice.

At the time, he appeared to be something of a Taylor Swift fan.

When news broke that she’d be co-hosting the 2013 Grammy nominations broadcast, Trump took to Twitter to share his approval: "Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5. Taylor is terrific!"

You should also read...

• Donald Trump's 7-word reaction to Taylor Swift's engagement leaves fans confused
• Former FBI Director James Comey confesses he's a massive Swiftie - and MAGA are furious

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