Inside Donald Trump’s hatred-fuelled ‘obsession’ with Taylor Swift as he makes fresh dig

Donald Trump has made yet another jibe at Taylor Swift after declaring that he ‘hates’ the pop megastar in September.

While normally the President of the United States of America is busy doing other stuff – like avoiding World War III, perhaps – Trump is busy teasing a 35-year-old pop star for getting booed at an NFL game. Makes sense.

Speaking while the Philadelphia Eagles were at the White House on Monday to celebrate their 2025 Super Bowl win against the Kansas City Chiefs, Trump nodded to the Getaway Car singer’s appearance at the Super Bowl, which she attended in support of the losing team’s tight end, her boyfriend Travis Kelce.

When both Trump and Swift attended the Super Bow in February, the pop star appeared on screen and was met by boos from the crowd. When Trump’s face popped up however, the reception was warmer.

At the time Trump smugly took to social media to suggest ‘the only one that had a tougher time than the Kansas City Chiefs was Taylor Swift. She got BOOED out of the Stadium. MAGA is very unforgiving!’

Now, he’s made yet another jibe about the moment (which Swift seemed to shrug off by giving the camera a side-eye).

‘Right from the beginning of the first quarter of the big game. I was there. I watched in person. I was there along with Taylor Swift, how did that work out?’ he said.

This most recent Swift dig has made Swifties suspect Trump is obsessed with the star.

‘Ugh he’s so obsessed,’ said @_jaidendavis. ‘What’s his problem? added @klaudiamepasoja, while @sel_dimandal said: ‘This old man never moved on..never matured eew.’

@ro76398725 added: ‘His one sided feud with a woman who is like 1/3 his age and is 100000 trillion times more successful, respected, and liked than him is honestly hilarious.’

‘Being a president of a country, he is targeting a pop star just because she does not support him. Why is he so obsessed? Really disgusting !’ noted @Ridz_0509.

Trump thought Taylor Swift would endorse him

With Swift’s country music origins, it seems Trump wrongly assumed her vote was his.

Rumour had it Swift was a secret Republican in the 2016 US election. But she shattered this suspicion in 2018, when the star publicly endorsed Tennessee Democratic candidates Phil Bredesen for Senate and Jim Cooper for House of Representatives in the mid-term elections.

‘In the past I’ve been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now,’ she wrote, nodding to 2016 when Trump began his first term as US President.

After that, Trump didn’t look on Swift so kindly. In fact, he told reporters he ‘liked Taylor’s music about 25% less now’.

In a 2023 interview for the 2024 book titled Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, Trump admitted he was surprised at Swift’s liberal stance.

This came during the first year of The Eras Tour as the country realised just how ground-breaking Swift’s popularity is.

Relaying his thoughts on the Shake It Off hitmaker, Trump complimented only her appearance and managed to refer to himself in the third person all in one breath.

‘I think she’s beautiful – very beautiful!’ Trump said. ‘I find her very beautiful. 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!’

He then asked: ‘She is liberal, or is that just an act? She’s legitimately liberal? It’s not an act? It surprises me that a country star can be successful being liberal.

Trump lashes out but remains hopeful Taylor Swift will endorse him

One thing Trump does recognise in Swift aside from her ‘beauty’ – ew – is her influence.

It’s not a stretch to say Swift could have political impact, as the size and dedication of her following are unmatched. In September 2023, the U.S. Travel Association estimated the Swift’s Eras Tour – the highest-grossing of all time – had a total economic impact surpassing $10 billion (£7.4bill). She’s the biggest star in the world.

So it’s easy to see why in that same 2023 interview, Trump stopped short of verbally attacking Swift and instead tried to undermine her own words, suggesting she’s lying about her political stance.

‘She’s got a great star quality,’ Trump said in Apprentice in Wonderland, nodding to her huge fame. ‘She really does.’

Since breaking her political silence in 2018, Swift has openly opposed Trump.

In 2020 she called him out on social media for ‘stoking the fires of white supremacy’ during the 2020 Black Lives Matter protests, declaring: ‘We will vote you out in November.’

After Trump’s attempt to dismantle the The United States Postal Service, Swift said he had ‘chosen to blatantly cheat and put millions of Americans’ lives at risk in an effort to hold on to power’.

‘Donald Trump’s ineffective leadership gravely worsened the crisis that we are in and he is now taking advantage of it to subvert and destroy our right to vote and vote safely,’ she added.

Swift explained in her Miss Americana film how she regretted not speaking out politically ahead of the 2016 elections.

 ‘I need to be on the right side of history,’ she said in an emotional scene.

Despite all her criticisms, Trump voiced his frustration at her for not endorsing him in June ahead of the November elections.

‘Why would she endorse this dope,’ Trump wondered, per CNN, of his then opponent Biden. ‘He doesn’t know how to get off a stage.’

While Swift never endorsed Biden, she did go on to voice support for his Democrat replacement Kamala Harris.

‘I’m voting for @kamalaharris because she fights for the rights and causes I believe need a warrior to champion them,’ Swift wrote.

Before Swift made her Harris vote public, Trump reposted an AI-created image of Swift endorsing him for US president in August.

This propelled Swift to act.

See more

‘Recently I was made aware that AI of ‘me’ falsely endorsing Donald Trump’s presidential run was posted to his site. It really conjured up my fears around AI, and the dangers of spreading misinformation,’ Swift wrote in her endorsement.

‘It brought me to the conclusion that I need to be very transparent about my actual plans for this election as a voter. The simplest way to combat misinformation is with the truth.’

Swift’s Instagram Story linked to the U.S. government’s Vote.gov, driving more than 400,000 visitors to the voter-information in the following 24-hour period.

Trump is tipped over the edge and declares he ‘hates’ Taylor Swift

This seriously rattled Trump, who has since thrown caution to the wind in his approach to Swift and her army of followers.

Chucking toys out the pram, Trump called into Fox News the morning after Swift’s endorsement and said he was ‘not a Taylor Swift fan’.

He added how he liked wife of Kansas City Chiefs quarterback Patrick Mahomes’ pro-Trump wife Brittany Mahomes ‘much better’ than her, reducing Swift’s stardom to that of a WAG.

‘It was just a question of time,’ Trump said. ‘You couldn’t possibly endorse Biden. But 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.’

Five days after Swift’s endorsement, still stewing, Trump took to Truth Social on a Sunday and wrote: ‘I HATE TAYLOR SWIFT!’.

Signed, The Smallest Man Who Ever Lived…

Got a story?

If you’ve got a celebrity story, video or pictures get in touch with the Metro.co.uk entertainment team by emailing us celebtips@metro.co.uk, calling 020 3615 2145 or by visiting our Submit Stuff page – we’d love to hear from you.