Of all the kind and gushing reactions to Taylor Swift and Travis Kelce’s headline-dominating engagement, the last one we expected was Donald Trump’s out-of-character well wishes.
The US President was asked about the news during a cabinet meeting and he told reporters: “Well, I wish them a lot of luck. 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.”
Quite the change of tune, as Trump has publicly bashed the pop megastar on numerous occasions, revealing a long and somewhat troubling fixation with Swift.
Trump has repeatedly attacked Swift, with his most recent outbursts on Truth Social saying that he “HATES” her and that she is “no longer HOT”.
Here’s a chronological – but by no means extensive – look back at some of the pettiest, most aggressive and frequently inconsistent comments Trump has made about Taylor Swift.
2009: The “Imma Let You Finish” Era
When Taylor Swift received the Best Female Video award at the MTV Video Music Awards for ‘You Belong With Me’ on 13 September 2009, Kanye West interrupted her acceptance speech – a notorious moment which has gone down in pop culture history.
At the time, Barack Obama called West a “jackass” and even Trump defended Swift, telling TMZ that Kanye should be boycotted “so this kind of thing doesn’t happen again.”
So far, so good.
2012: The Swiftie Era
When news broke in 2012 that Taylor Swift would be co-hosting the 2013 Grammy nominations broadcast, Trump posted on Twitter: “Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5. Taylor is terrific!”
Still civil.
2018: The Percentage Era
Swift made headlines in 2018 by openly endorsing a candidate for the first time: Tennessee Democrat Phil Bredesen.
Trump told reporters outside the White House: “Marsha Blackburn (Bredesen’s opponent) is doing a very good job in Tennessee. She’s leading now substantially, which she should. She’s a tremendous woman. I’m sure Taylor Swift doesn’t know anything about her. And let’s say that I like Taylor’s music about 25 per cent less now, OK?”
That’s still a 75 per cent approval rating…
2023: The Musically Challenged Era
Things get competitive, as Trump was celebrating his very own music career in 2023.
A single had been released by a choir of men in prison for their participation in the attack on the US Capitol on 6 January 2021. The track by the J6 Prison Choir, titled ‘Justice for All’, featured a recording by Trump as the backing track.
Once released, Trump claimed that the song was outperforming Taylor Swift in the charts. “It beat Taylor Swift, it beat Miley Cyrus, who was number one and two,” he said at a rally.
Pettiness levels rising…
2024: The HATE Era
2024 was the year Trump’s Swift obsession fully bloomed, leading him to publicly declare his hatred for Swift.
The year didn’t start off too badly. Creepily, though.
At the start of the election year, Trump said Swift would be “disloyal” to him if she were to endorse Joe Biden. Then, in June, he commented on Swift’s appearance during a Variety interview with author Ramin Setoodeh, who wrote the book “Apprentice In Wonderland: How Donald Trump And Mark Burnett Took America Through The Looking Glass”. He told Setoodeh: “I think she’s beautiful – very beautiful!” He followed that comment with a more dubious compliment, calling Swift “unusually beautiful.” During the same interview, Trump also questioned whether the singer was “legitimately liberal.”
Trump then posted AI-generated images suggesting Swift had endorsed him, clearly showing that he coveted her endorsement.
However, when Swift hit back at the fake images and endorsed Kamala Harris, Trump very presidentially posted on his Truth Social media account, in all-caps: “I HATE TAYLOR SWIFT!” Clearly riled by her allegiance to Harris, he added that Swift would “probably pay a price” for her support of the Democratic candidate.
Trump’s outburst led to the trending phrase “I love Taylor Swift”.
2025: The Violent Flip-Flop Era
Strap in for this one.
During the 2025 Super Bowl, Swift appeared on screen and boos could be heard in the crowd. Trump didn’t skip a beat and immediately posted on Truth Social: “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!”
In May, and without any discernable reason or prompt, he lashed out on Truth Social, writing: “Has anyone noticed that, since I said ‘I HATE TAYLOR SWIFT,’ she’s no longer ‘HOT?’”
This month, Trump took the time to share his thoughts about the Sydney Sweeney / American Eagle controversy, and decided to drag Swift’s name into the debate.
He wrote: “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.”
A sizeable U-turn when taking into consideration his previous “beautiful” comments.
But just when the whiplash hadn’t settled came Trump’s engagement reaction: “I think that she’s a terrific person. So I wish them a lot of luck.”
Has Trump secretly joined ranks with former FBI chief James Comey, who controversially confessed last week that he was a massive Swiftie? Was it a classy move on his part to put the bad blood behind him once and for all? Or did he simply forget he “HATES” Taylor Swift, meaning we will probably be treated to another Truth Social rant soon?
Whatever the reason for this sudden change of heart, we’re betting that this isn’t the end of Trump’s obsession with Swift – or any celebrity who doesn’t side with him. We’ve still got four more months in this era.
