President Trump and Taylor Swift's Tense History, Revisited

Yahoo

08-02-2025

President Donald Trump and Taylor Swift, both set to attend the 2025 Super Bowl, have a tense history in the public forum. Credit - President Donald Trump: Kevin Dietsch—Getty Images, Taylor Swift: Brooke Sutton—Getty Images
Super Bowl LIX sees the Kansas City Chiefs and Philadelphia Eagles playing against one another for the ultimate trophy win. But those teams won't be the only adversaries present at New Orleans' Caesars Superdome. President Donald Trump and musician Taylor Swift will also be in attendance.
Trump, the 2024 TIME Person of the Year, and Swift, who received TIME's Person of the Year title in 2023, have a complicated past. Both parties have called one another out over opposing political views and actions. After staying away from publicly commenting on politics during the beginning of her career, Swift endorsed a Democratic candidate in the U.S. Senate election in Tennessee in 2018. Trump publicly responded to Swift's endorsement, and various comments have been made by both sides since.
In light of both Trump and Swift attending the Super Bowl, here's a look back at their tense history.
Though Swift had, prior to this, stayed away from political endorsements, she decided in 2018 to voice her support for Democratic senatorial candidate Phil Bredesen over Republican candidate Blackburn. Swift said Blackburn's voting record in Congress 'appalls and terrifies" her.
At the White House a few days later, Trump was asked about the endorsement by reporters.
'I'm sure Taylor Swift doesn't know anything about [Blackburn],' Trump said, adding, 'I like Taylor's music about 25% less now, OK?'
In an interview with the Guardian, Swift publicly criticized Trump after not endorsing a candidate during the 2016 election. When asked about the Trump Administration by the publication, she said:
'We're a democracy—at least, we're supposed to be—where you're allowed to disagree, dissent, debate. I really think that he thinks this is an autocracy,' she said.
She also told the outlet that she felt 'really remorseful for not saying anything' during the 2016 election between Trump and Democratic candidate Hillary Clinton.
In her 2020 Netflix documentary, Miss Americana, Swift took fans behind the scenes of her decision to endorse Tennessee Democratic candidate Bredesen in his Senate race against Republican candidate Blackburn, which was ultimately won by Blackburn.
In the documentary, Swift refers to Blackburn as 'Trump in a wig.'
Swift took a strong stand against the President in the midst of the protests after the killing of George Floyd. Trump posted on X (formerly Twitter), warning protesters in Minnesota that 'when the looting starts, the shooting starts.' Trump's post was then flagged by Twitter—two years before the platform was bought by Trump supporter and DOGE leader Elon Musk—for 'glorifying violence.'
Swift then took to the same social media platform to address Trump directly. 'After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence?' she wrote. ''When the looting starts the shooting starts'??? We will vote you out in November. @realdonaldtrump.'
In August 2020, Trump admitted that he opposed additional funding for the United States Postal Service (USPS) in order to make it more difficult to deliver mail-in ballots.
On X, Swift called out the President over his actions.
'Trump's calculated dismantling of USPS proves one thing clearly: He is WELL AWARE that we do not want him as our President,' she wrote. 'He's chosen to blatantly cheat and put millions of Americans' lives at risk in an effort to hold on to power.'
In her first presidential endorsement, Swift decided to officially support President Joe Biden over Trump in the latter's first re-election campaign. In a fall 2020 issue of V Magazine, Swift told the outlet that 'the change we need most is to elect a President who recognizes that people of color deserve to feel safe and represented, that women deserve the right to choose what happens to their bodies, and that the LGBTQIA+ community deserves to be acknowledged and included.'
When the issue came out, Swift shared the interview on social media, joking that it was 'so apt that it [came] out on the night of the VP debate.' The singer added that she would be 'watching and supporting' then-Vice Presidential candidate Kamala Harris 'by yelling at the TV a lot.'
In 2023, Trump embraced a song sung by a group of defendants incarcerated over their alleged roles in the Jan. 6, 2021, insurrection. The song, 'Justice for All' was played by Trump during several rallies throughout 2023, and briefly jumped to Number 1 on iTunes, according to the Associated Press.
In a rally later in 2023, Trump referenced the song, telling a crowd in Houston, Texas, '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.'
When the presidential race was raging on between Biden and Trump, prior to Harris taking over as the Democratic candidate, Trump released a statement on Truth Social, claiming credit for the 2018 Music Modernization Act and stating that Swift would not endorse Biden's re-election bid.
'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,' he wrote. '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'
CNN Capitol Hill reporter Melanie Zanona posted on X that Trump questioned Swift's support of then-opponent President Biden in a meeting with House Republicans.
'Why would she endorse this dope?' Trump said, according to Zanona's reporting. 'He doesn't know how to get off a stage.'
The topic of Trump and Swift became a talking point once again amid the June 18 release of a book titled Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, written by Variety co-editor-in-chief Ramin Setoodeh. The author shares comments Trump reportedly made about Swift during a conversation in November 2023.
'I think she's beautiful—very beautiful! I think she's liberal' Trump is quoted as saying in his conversation with Setoodah. 'She probably doesn't like Trump. I hear she's very talented. I think she's very beautiful actually—unusually beautiful.'
In mid-August 2024, Trump posted a series of images on Truth Social seemingly showing Taylor Swift fans wearing T-shirts that read 'Swifties for Trump.' But the images had been created using AI.
'I accept!' the caption to the post read, signalling Trump's acceptance of an endorsement that was AI-generated and not real.
Soon after Trump's debate with Harris ended, Swift took to social media and officially endorsed the former Vice President.
'Like many of you, I watched the debate tonight,' Swift wrote in an Instagram post on Sept. 10 to her over 200 million followers. 'I will be casting my vote for Kamala Harris and Tim Walz in the 2024 Presidential Election. I'm voting for @kamalaharris because she fights for the rights and causes I believe need a warrior to champion them."
She signed the post with her name, followed by 'Childless Cat Lady'—a reference to Vice President J.D. Vance's controversial comments about his Democratic opponents and women who choose not to give birth, calling them 'childless cat ladies.'
Read More: Watch Tim Walz React to Endorsement From 'Fellow Cat Owner' Taylor Swift
Swift also said in the post that she was 'made aware that AI of 'me' falsely endorsing Donald Trump's presidential run was posted to his site,' and that this spurred her to clear up the confusion around her political views.
https://www.instagram.com/p/C_wtAOKOW1z
On the TV show Fox & Friends, Trump was asked about Swift's endorsement of his opponent, Harris. In response, Trump said that he liked 'Mrs. Mahomes'—referencing Brittany Mahomes, the wife of Kansas City Chiefs quarterback Patrick Mahomes— better than Swift. Swift is currently dating the Chiefs' tight end Travis Kelce.
'She's a very liberal person,' Trump said of the pop star. 'She seems to always endorse a Democrat and she'll probably pay a price for it in the marketplace.'
Five days after Swift endorsed Harris for President, Trump posted 'I HATE TAYLOR SWIFT!' on his social media app, Truth Social.
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