From ‘I Hate Her’ to ‘Terrific Person’: Trump’s Surprising Take on Taylor Swift’s Engagement” A stunning reversal as Donald Trump wishes luck to Taylor Swift and Travis Kelce after years of public jabs.
Despite his many public criticisms, U.S. President Donald Trump extended his warmest wishes to pop star Taylor Swift and American football star Travis Kelce after confirming their engagement. The announcement was accompanied by a joint Instagram post from Swift and Kelce, captioned: “Your English teacher and your PE teacher are getting married.”
During a cabinet meeting on August 26, 2025, Trump was asked about the news. He replied, “I wish them well. I think he’s a great man. I think she’s a great person.” This marked a significant shift from Trump’s previous harsh statements against Swift, particularly during and after the 2024 presidential election, when Swift publicly endorsed the Democratic candidate.
Trump’s criticism of Swift has continued over the past year, particularly targeting her political supporters. Earlier in 2025, Trump expressed his contempt for Swift on his Truth Social platform, loudly declaring, “I hate Taylor Swift!” He also claimed that Swift was no longer popular because of her “enlightened” views, writing, “She was kicked out of the Super Bowl. She’s not popular anymore.” He compared this to his praise of actress Sydney Sweeney’s American Eagle Jeans commercial, calling it an example of how “an avowed Republican” can succeed.
In February 2025, Trump shared a video from the Super Bowl in which Swift, who was supporting Kelsi, was booed by the crowd. Trump commented on the video, saying, “Trump gets massive cheers at the Super Bowl, while Taylor Swift gets booed—the world is healing!” He then mocked her again, saying, “The only person who had a tougher night than the Kansas City Chiefs was Taylor Swift. She got kicked out of the stadium.” MAKE AMERICA GREAT AGAIN is ruthless!”
In February 2025, Trump posted a video from the Super Bowl in which Swift, who was cheering for Kelsi, was booed by the crowd. Trump commented on the video, saying, “Trump is being cheered at the Super Bowl, Taylor Swift is being booed—the world is healing!” He then mocked her again, saying, “The only person who had a harder night than the Kansas City Chiefs was Taylor Swift. She was booed off the field. ‘Make America Great’ is ruthless!”
Swift remained silent in the face of Trump’s repeated attacks.
The couple’s engagement sparked widespread interest on social media. Swift’s Instagram post included a series of romantic photos of Kelsi proposing in a lush garden. The singer sported an antique cushion-cut diamond ring on a gold band, with floral arrangements described as simple yet elegant.
Travis Kelce’s father, Ed Kelce, revealed that the proposal took place on August 10, shortly after recording a podcast with his brothers. The couple had been dating since 2023, with Swift becoming a regular fixture at Kansas City Chiefs games. Their recent engagement marks a new chapter, celebrated by their return to Arrowhead Stadium for their first public appearance since the announcement.
Trump’s surprisingly warm tone toward Swift and Kelce during the Cabinet meeting could be seen as a departure from his previous negative comments, but it remains to be seen whether this shift marks a lasting evolution in their personal and public relationship.