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Super Bowl LIX is gearing up for an exciting clash between the Kansas City Chiefs and the Philadelphia Eagles at the Caesars Superdome in New Orleans. Yet, the event’s allure extends beyond the game itself, as two prominent attendees—President Donald Trump and pop music icon Taylor Swift—are expected to make headlines.

Trump, named TIME’s Person of the Year for 2024, shares a complicated relationship with Swift, who received the same honor in 2023. Their interactions are underscored by significant political differences. Initially, Swift maintained a low profile regarding her political beliefs, but in 2018, she made headlines by endorsing Democratic candidate Phil Bredesen in Tennessee and criticized Republican Marsha Blackburn’s congressional voting record, labeling it as “appalling and terrifying.” This endorsement sparked a response from Trump and ignited an ongoing exchange between them.

With both Trump and Swift attending the Super Bowl, it’s a fitting moment to reflect on their tumultuous history.

October 2018: Trump Responds to Swift’s Political Stance

In a significant departure from her previous stance, Swift publicly backed Phil Bredesen for the Senate, voicing her concerns about Blackburn’s voting history. This prompted Trump to comment during a White House press briefing, stating, “I’m sure Taylor Swift doesn’t know anything about [Blackburn]. I like Taylor’s music about 25% less now, OK?”

August 2019: Swift Challenges Trump’s Leadership

Swift escalated her criticisms in an interview with the Guardian, expressing apprehensions about Trump’s view 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 commented. She also reflected on her regret for not speaking out 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 elaborated on her rationale for endorsing Bredesen, describing Blackburn as “Trump in a wig.”

May 29, 2020: Swift Declares “We Will Vote You Out”

In the wake of protests following George Floyd’s death, Swift condemned Trump’s incendiary social media comments. She remarked, “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 Critiques Trump’s USPS Actions

In August 2020, Trump admitted to obstructing funding for the USPS, aiming to hinder mail-in voting. Swift addressed his actions on social media, 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 Supports Biden

Swift officially endorsed Joe Biden in his campaign against Trump, stressing the importance of a leader who champions the rights of marginalized communities. In a fall 2020 edition of V Magazine, she articulated the necessity 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 aligned perfectly with a Vice Presidential debate, expressing her intention to support Kamala Harris by “yelling at the TV a lot.”

November 2023: Trump Claims His Song “Outperformed Taylor Swift”

In 2023, Trump drew attention by promoting a song performed by individuals associated with the January 6 insurrection. The song, titled “Justice for All,” gained traction at his rallies and climbed the iTunes charts. Trump boasted at a rally in Houston, asserting, “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 Contributed to Swift’s Wealth

As the presidential race heated up, Trump took to Truth Social to tout his role in the success of the Music Modernization Act, suggesting it had 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 Biden Endorsement

Reports surfaced that Trump expressed disbelief regarding Swift’s endorsement of Biden during a gathering with House Republicans, questioning, “Why would she endorse this dope?”

June 18, 2024: Trump Comments on Swift’s Appearance

While promoting 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

In mid-August 2024, Trump posted AI-generated images that falsely depicted Swift fans wearing “Swifties for Trump” shirts, suggesting a non-existent endorsement. He captioned the post, “I accept!” indicating 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

After a debate between Trump and Harris, Swift announced her endorsement of the former Vice President on social media. In an Instagram post, she declared her intent to vote for Harris, highlighting the significance of having a champion for the causes she champions.

Swift added a humorous touch by signing the post as “Childless Cat Lady,” a nod to derogatory remarks made by Trump’s allies about women without children.

She also clarified that she aimed to dispel any misconceptions arising from the AI-generated images that falsely portrayed her endorsement of Trump.

Read More: Watch Tim Walz React to Endorsement From ‘Fellow Cat Owner’ Taylor Swift

Sept. 11, 2024: Trump Critiques Swift in an Interview

During a segment on Fox & Friends, Trump dismissed Swift’s endorsement of Harris, expressing a preference for Brittany Mahomes over her. He stated, “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.”

Sept. 15, 2024: Trump Declares “I Hate” Swift

Just five days after Swift endorsed Harris, Trump took to Truth Social to voice his contempt, posting bluntly, “I HATE TAYLOR SWIFT!”