During a Monday morning press conference, White House Press Secretary Karoline Leavitt was thrown off course when a reporter blindsided her with a question about President Donald Trump’s latest social media attack on Taylor Swift.
The unexpected inquiry from Fox News reporter Peter Doocy drew audible chuckles from the press briefing room, including from Leavitt herself.
The question stemmed from Trump’s May 16 Truth Social post where he wrote, “Has anyone noticed that, since I said ‘I HATE TAYLOR SWIFT,’ she’s no longer ‘HOT?’”
This latest jab marks another chapter in the ongoing feud between the president and the music icon, which intensified during the 2024 presidential campaign after Swift publicly endorsed Democrat Kamala Harris over Trump. In Sept. 2024, he wrote on the same app, ” ‘I HATE TAYLOR SWIFT.”
Doocy asked, “What does President Trump mean when he says that Taylor Swift is no longer ‘hot?’”
The press secretary had a smirk when she answered.
“Look, he is speaking about Taylor Swift’s political views and how perhaps it has impacted the support of the American public for her work,” Leavitt said. “And I’ll leave it at that.”
The friction between Trump and Swift dates back to September 2024, when Swift endorsed Harris for president.
In response, Trump minced no words, immediately posting “I HATE TAYLOR SWIFT!” on Truth Social. Following her endorsement on Instagram, Swift helped drive hundreds of thousands of people to register to vote, potentially impacting the election’s outcome.
Social media users were quick to respond to the viral exchange between Doocy and Leavitt.
One X user tweeted, “I wish Trump would learn to shut up about celebrities. Enough. I’m tired of it.”
Another defended Swift, stating, “He’s jealous because she actually works for her wealth, not given to her.”
Others seemed more outraged at Leavitt for not offering clarity in answering the reporter’s question.
“As usual Leavitt can’t give a straight or honest answer… If she did she would choke on it,” said one person, while another added, “With leavitt taking her usual swing and a miss to most questions, this response didn’t help her average…….”
Coming to her defense, one person said, “KL wasn’t “forced” to answer this question, she just answered it. Stop making it a bigger deal.”
The president’s fixation on Swift continued when the Philadelphia Eagles visited the White House last month to celebrate their Super Bowl LIX victory over the Kansas City Chiefs. During the ceremony, Trump couldn’t resist taking a dig at Swift, who attended the game supporting her boyfriend, Chiefs tight end Travis Kelce.
“I was there along with Taylor Swift,” Trump remarked during the South Lawn celebration, before asking the crowd with a smirk, “How did that work out?”
The Swift controversy isn’t the only celebrity feud Trump has engaged in recently. Rock legend Bruce Springsteen became his latest target after criticizing the administration during a concert in Manchester, England.
Springsteen told the British crowd, “In my home, the America I love, the America I’ve written about that has been a beacon of hope and liberty for 250 years is currently in the hands of a corrupt, incompetent and treasonous administration.”
Trump fired back on Truth Social, calling Springsteen “Highly Overrated” and “dumb as a rock.” Right-leaning magazine Outkick posted a video of Springsteen’s comments with the caption, “Imagine buying tickets to a Bruce Springsteen concert and just getting an ‘America bad’ lecture the whole time.”
Meanwhile, Barstool Sports founder Dave Portnoy found himself in an awkward position as both a Trump supporter and self-proclaimed “Swiftie.”
According to Awful Announcing, when Fox Business host Stuart Varney asked Portnoy about the president’s claim that Swift is “no longer hot,” the sports media personality was put in the uncomfortable position of debating the pop star’s attractiveness on national television.
“I’m not upset with Trump. Trump’s Trump, so that was not a surprising thing,” Portnoy stated on Awful Announcing.
Adding, “I mean, he’s wrong. Like, you can’t be more wrong about anything. Taylor Swift is as hot as she’s ever been in the streets. She hasn’t put out new music, but if she said, ‘hey, snap my fingers, I want to sell 500,000 or a million tickets in three seconds and break Live Nation, she’d do it.”
In 2025, politics, entertainment, and social media remain deeply intertwined in Trump’s presidency. Celebrities like Swift and Springsteen have openly clashed with him, yet many of his supporters still admire them.
Now, Trump loyalists face a real dilemma: How do you support both your Commander-in-Chief and global music icons?
Whether on social media, at press conferences, or on podcasts, the tension grows—especially since Trump believes his cult-like following outshines theirs.
