This softer tone contrasts sharply with his recent posts online where he had attacked the pop star.
From public taunts to praise
Earlier this month, Trump wrote on Truth Social: “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.”
It was not an isolated remark. Trump has regularly criticised Swift since she began endorsing Democratic candidates, most recently Kamala Harris and Tim Walz in the 2024 presidential election. Soon after Swift declared on Instagram, “I will be casting my vote for Kamala Harris and Tim Walz in the 2024 Presidential Election,” Trump responded with “I HATE TAYLOR SWIFT” on Truth Social.
He mocked her again in February when she appeared at the Super Bowl in support of Kelce, writing: “Trump gets massive cheers at the Super Bowl while Taylor Swift gets booed – The world is healing!” In another post, he added: “The only one that had a tougher night than the Kansas City Chiefs was Taylor Swift. She got BOOED out of the Stadium. MAGA is very unforgiving!”
Sydney Sweeney and the ‘hotness’ row
Trump’s hostility toward Swift was heightened during the Sydney Sweeney American Eagle campaign. Praising the actress, whom he described as a “registered Republican,” Trump contrasted her with Swift. He posted: “Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there. It’s for American Eagle, and the jeans are ‘flying off the shelves’. Go get ‘em Sydney. 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.”
He concluded with, “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!”
Taylor Swift and Travis Kelce’s announcement
Against this backdrop, Swift and Kelce’s announcement took social media by storm. On Tuesday, the pair shared a joint Instagram post with photos of a rose garden proposal and a close-up of the ring. Their caption read: “Your English teacher and your gym teacher are getting married.”
Kelce’s father has since revealed that the proposal had actually taken place weeks earlier. The Kansas City Chiefs also welcomed Swift to the team family, posting: “Congrats to Travis and Taylor – we’re excited to have you as a permanent member of the Chiefs Kingdom family!” with the added line, “Today is a fairytale.”
A relationship in the spotlight
Swift and Kelce first became linked in 2023 when he reached out during her Eras Tour. By autumn of that year, she was spotted at a Chiefs game and the relationship quickly became headline news. Swift has since been a regular at games, while Kelce appeared with her in podcast episodes and public events.
Earlier this month, Swift joined Kelce’s “New Heights” podcast to promote her twelfth studio album, The Life of a Showgirl. The episode set a Guinness World Record for live podcast viewership on YouTube, underscoring their combined influence across sport and music.
Swift’s open support for Democrats has often put her at odds with Trump. In a 2020 Fox & Friends interview, he remarked: “I was not a Taylor Swift fan. It was just a question of time. She 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.”
Despite this history, Trump’s reaction to the engagement marks a rare moment of goodwill. For Swift and Kelce, the announcement represents not only a personal milestone but also a cultural one, uniting fans of American football and global pop music in a single story.
