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Super Bowl LIX is set to showcase a thrilling matchup between the Kansas City Chiefs and the Philadelphia Eagles at the Caesars Superdome in New Orleans. However, the spotlight won’t just be on the field as two notable figures—President Donald Trump and pop sensation Taylor Swift—are also slated to attend the event.
Trump, named TIME’s Person of the Year for 2024, and Swift, who received the same accolade in 2023, have a complex relationship marked by sharp political disagreements. Initially, Swift kept her political views private but broke her silence in 2018 by endorsing Democratic candidate Phil Bredesen in Tennessee, firmly opposing Republican Marsha Blackburn, whose congressional voting record she criticized as “appalling and terrifying.” This endorsement drew a direct response from Trump and has fueled a back-and-forth dialogue between the two since then.
With both Trump and Swift attending the Super Bowl, let’s revisit their fraught history.
October 2018: Trump reacts to Swift’s Democratic endorsement
In a notable shift, Swift publicly endorsed Phil Bredesen for the Senate, diverging from her previous apolitical stance. She expressed her dismay over Blackburn’s voting history, which prompted Trump to comment on the matter during a White House press briefing.
“I’m sure Taylor Swift doesn’t know anything about [Blackburn],” Trump remarked, adding, “I like Taylor’s music about 25% less now, OK?”
August 2019: Swift critiques Trump’s governance
Swift took her criticisms further in an interview with the Guardian, expressing her concerns about Trump’s approach to democracy. “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 stated.
She also expressed regret for not taking a stand during the 2016 election.
Read More: Donald Trump is the 2024 TIME Person of the Year
January 2020: Insights from Swift’s Miss Americana documentary
In her documentary Miss Americana, Swift delved into her motivations for endorsing Bredesen, referring to Blackburn as “Trump in a wig.”
May 29, 2020: Swift tells Trump “we will vote you out”
Following the protests after George Floyd’s death, Swift publicly condemned Trump for his inflammatory remarks on social media. In a powerful response, she wrote, “After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority… We will vote you out in November. @realdonaldtrump.”
August 2020: Swift criticizes Trump’s USPS stance
In August 2020, Trump openly admitted to blocking funding for the USPS to complicate mail-in voting. Swift took to social media to address his actions, stating, “Trump’s calculated dismantling of USPS proves one thing clearly: He is WELL AWARE that we do not want him as our President.”
October 2020: Swift backs Biden over Trump
Swift officially endorsed Joe Biden in his campaign against Trump, emphasizing the need for a leader who supports the rights of marginalized communities. In a fall 2020 issue of V Magazine, she stated the importance of electing a President who recognizes the need for representation and safety for people of color, women, and the LGBTQIA+ community.
Upon the magazine’s release, she humorously noted on social media that the timing coincided perfectly with a VP debate, adding her intention to support Kamala Harris by “yelling at the TV a lot.”
November 2023: Trump claims his song “beat Taylor Swift”
In 2023, Trump made headlines when he championed a song performed by individuals involved in the January 6 insurrection. The track, titled “Justice for All,” gained popularity at his rallies and reached the top of iTunes charts. Trump boasted at a rally in Houston, claiming, “It beat Taylor Swift, it beat Miley Cyrus,” highlighting his competitive spirit.
Read More: Taylor Swift is the 2023 TIME Person of the Year
February 2024: Trump claims he’s made Swift “so much money”
Amid the intensifying presidential race, Trump took to Truth Social to credit himself for the success of the Music Modernization Act, asserting that it benefited Swift. He claimed, “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.”
June 14, 2024: Trump questions Swift’s endorsement of Biden
Reports emerged that Trump expressed disbelief over Swift’s endorsement of Biden during a meeting with House Republicans, questioning, “Why would she endorse this dope?”
June 18, 2024: Trump remarks on Swift’s beauty
In conjunction with the release of a book about his life, Trump was quoted discussing Swift, saying, “I think she’s beautiful—very beautiful! I think she’s liberal.”
August 2024: Trump shares AI-generated images of Swift supporting him
In mid-August 2024, Trump posted AI-generated images appearing to show Swift fans wearing “Swifties for Trump” shirts, mistakenly suggesting a false endorsement. He captioned the post, “I accept!” signaling his acceptance of the fabricated support.
Read More: Are You Ready For It? How Harris’ Campaign Is Marketing Taylor Swift’s Endorsement
Sept. 10, 2024: Swift officially endorses Harris
Following a debate between Trump and Harris, Swift took to social media to announce her endorsement of the former Vice President. In an Instagram post, she expressed her intent to vote for Harris, emphasizing the importance of having a champion for the causes she believes in.
She humorously signed the post as “Childless Cat Lady,” referencing derogatory comments made by Trump’s allies about women without children.
Swift clarified that she wanted to correct any misconceptions stemming from the AI-generated images falsely portraying her endorsement of Trump.
Read More: Watch Tim Walz React to Endorsement From ‘Fellow Cat Owner’ Taylor Swift
Sept. 11, 2024: Trump disparages Swift in an interview
During an appearance on Fox & Friends, Trump dismissed Swift’s endorsement of Harris, claiming he preferred Brittany Mahomes over her. He added, “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.”
Anna Barclay—Getty Images
Sept. 15, 2024: Trump declares “I hate” Swift
Just five days post-Swift’s endorsement of Harris, Trump took to Truth Social to express his disdain, posting outright, “I HATE TAYLOR SWIFT!”
