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Super Bowl LIX promises to deliver an exhilarating clash between the Kansas City Chiefs and the Philadelphia Eagles at the iconic Caesars Superdome in New Orleans. Yet, the attention will extend beyond the gridiron, as prominent personalities—former President Donald Trump and music superstar Taylor Swift—are confirmed to make their presence felt at the event.
Trump, recently recognized as TIME’s Person of the Year for 2024, shares an intriguing yet contentious history with Swift, who earned the same honor in 2023. Their relationship has been marked by stark political contrasts. Initially, Swift maintained a low profile regarding her political beliefs, but in 2018 she broke that silence by endorsing Democratic candidate Phil Bredesen in Tennessee, openly challenging Republican Marsha Blackburn and condemning her congressional voting record as “appalling and terrifying.” This endorsement elicited a sharp reaction from Trump and has since sparked ongoing exchanges between the two.
With both Trump and Swift attending the Super Bowl, it’s an opportune moment to reflect on their turbulent interactions over the years.
October 2018: Trump responds to Swift’s endorsement
Swift made headlines when she openly endorsed Phil Bredesen for the Senate, marking a shift from her prior stance of political neutrality. She articulated her concerns about Blackburn’s voting history, prompting Trump to weigh in during a White House press briefing.
“I’m sure Taylor Swift doesn’t know anything about [Blackburn],” Trump quipped, adding, “I like Taylor’s music about 25% less now, OK?”
August 2019: Swift critiques Trump’s administration
Swift escalated her criticisms in an interview with the Guardian, voicing her apprehensions about Trump’s understanding of 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 remarked.
She later expressed regret for her silence during the 2016 election cycle.
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 shared her reasons for supporting Bredesen, referring to Blackburn as “Trump in a wig.”
May 29, 2020: Swift tells Trump “we will vote you out”
In the wake of protests following George Floyd’s death, Swift condemned Trump for his incendiary comments on social media. In a powerful statement, she declared, “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 challenges Trump’s USPS actions
In August 2020, Trump acknowledged blocking funding for the USPS to hinder mail-in voting. Swift took to social media to criticize his actions, asserting, “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 endorses Biden over Trump
Swift formally endorsed Joe Biden in his run against Trump, highlighting the necessity of a leader who advocates for the rights of marginalized groups. In an issue of V Magazine in fall 2020, she emphasized the importance of electing a President who acknowledges 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 was perfect for a VP debate, vowing to support Kamala Harris by “yelling at the TV a lot.”
November 2023: Trump claims his song “beat Taylor Swift”
In 2023, Trump gained attention for promoting a song by artists involved in the January 6 insurrection. The song, titled “Justice for All,” saw significant traction at his rallies and reached the top of the iTunes charts. Trump remarked at a Houston rally, “It beat Taylor Swift, it beat Miley Cyrus,” showcasing his competitive nature.
Read More: Taylor Swift is the 2023 TIME Person of the Year
February 2024: Trump claims he’s made Swift “so much money”
As the presidential race heated up, Trump took to Truth Social to claim credit for the Music Modernization Act’s success, asserting that it had financially benefited Swift. He stated, “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 Biden endorsement
Reports surfaced indicating that Trump expressed skepticism about Swift’s endorsement of Biden during a meeting with House Republicans, questioning, “Why would she endorse this dope?”
June 18, 2024: Trump comments on Swift’s looks
In conjunction with a book release discussing his life, Trump was quoted as 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 shared AI-generated images that appeared to show Swift fans wearing “Swifties for Trump” shirts, misleadingly suggesting her endorsement. He captioned the post, “I accept!” indicating his approval of the fictional support.
Read More: Are You Ready For It? How Harris’ Campaign Is Marketing Taylor Swift’s Endorsement
Sept. 10, 2024: Swift officially endorses Harris
After 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 stated her intention to vote for Harris, emphasizing the significance of having a champion for the causes she believes in.
She humorously signed off the post as “Childless Cat Lady,” a nod to derogatory remarks made by Trump’s supporters about women without children.
Swift also clarified her stance, aiming to dispel any confusion caused by the AI-generated images that falsely depicted her as endorsing Trump.
Read More: Watch Tim Walz React to Endorsement From ‘Fellow Cat Owner’ Taylor Swift
Sept. 11, 2024: Trump belittles Swift in an interview
During his appearance on Fox & Friends, Trump dismissed Swift’s endorsement of Harris, suggesting he preferred Brittany Mahomes over her. He remarked, “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 after Swift’s endorsement of Harris, Trump took to Truth Social to air his grievances, bluntly stating, “I HATE TAYLOR SWIFT!”
