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Super Bowl LIX is poised to deliver an exhilarating contest between the Kansas City Chiefs and the Philadelphia Eagles at the Caesars Superdome in New Orleans. Yet, the event will also feature high-profile attendees, including former President Donald Trump and music icon Taylor Swift.
Trump, honored as TIME’s Person of the Year for 2024, and Swift, who held the title in 2023, have a contentious history characterized by stark political divides. Although Swift initially refrained from sharing her political opinions, she made headlines in 2018 by endorsing Phil Bredesen, a Democratic candidate in Tennessee, while vocally opposing Republican Marsha Blackburn. Swift described Blackburn’s congressional record as “appalling and terrifying.” This endorsement sparked a fiery exchange between the two, setting the stage for ongoing tensions.
With both Trump and Swift present at the Super Bowl, it’s a fitting moment to reflect on their turbulent relationship.
October 2018: Trump reacts to Swift’s endorsement of Bredesen
In a significant departure from her previous stance, Swift publicly supported Phil Bredesen for the Senate, criticizing Blackburn’s voting record. This prompted a reaction from Trump at 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 voices concerns about Trump’s leadership
Swift escalated her criticisms in an interview with the Guardian, expressing worries about Trump’s impact on 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.
Additionally, she expressed remorse for not taking a firmer stance during the 2016 presidential 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 elaborated on her reasons for endorsing Bredesen, describing Blackburn as “Trump in a wig.”
May 29, 2020: Swift tells Trump “we will vote you out”
Following the protests ignited by George Floyd’s death, Swift condemned Trump’s inflammatory social media posts. 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 criticizes Trump’s USPS stance
In August 2020, Trump openly acknowledged that he was blocking funding for the USPS to hinder mail-in voting. Swift responded on social media, 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 officially backed Joe Biden in his race against Trump, stressing the necessity for a leader who champions the rights of marginalized groups. In a fall 2020 issue of V Magazine, she emphasized the importance of electing a President who understands 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, hinting at 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 drew attention by promoting a song performed by individuals associated with the January 6 insurrection. The track, titled “Justice for All,” became a hit at his rallies and topped the iTunes charts. Trump boasted at a Houston rally, claiming, “It beat Taylor Swift, it beat Miley Cyrus,” reflecting 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 intensified, Trump took to Truth Social to credit himself for the success of the Music Modernization Act, claiming it 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 endorsement of Biden
Reports surfaced that Trump was incredulous about Swift’s endorsement of Biden during a meeting with House Republicans, asking, “Why would she endorse this dope?”
June 18, 2024: Trump comments on Swift’s appearance
As he released a book about his life, Trump was quoted discussing Swift, stating, “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 depict Swift fans wearing “Swifties for Trump” shirts, falsely suggesting her endorsement. He captioned the post, “I accept!” indicating his embrace 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
After a debate between Trump and Harris, Swift used social media to declare her endorsement of the former Vice President. In an Instagram post, she signaled her intent to vote for Harris, underscoring the importance of having a champion for the causes she cares about.
She humorously concluded the post as “Childless Cat Lady,” a nod to derogatory comments made by Trump’s supporters regarding women without children.
Swift also clarified her desire to dispel any misconceptions stemming from the AI-generated images that inaccurately suggested her endorsement of Trump.
Read More: Watch Tim Walz React to Endorsement From ‘Fellow Cat Owner’ Taylor Swift
Sept. 11, 2024: Trump dismisses Swift in an interview
During an interview on Fox & Friends, Trump downplayed Swift’s endorsement of Harris, claiming 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 endorsed Harris, Trump took to Truth Social to vent his frustration, declaring, “I HATE TAYLOR SWIFT!”
