Super Bowl LIX saw the Philadelphia Eagles beat the Kansas City Chiefs 40-22 for the ultimate trophy win. But those teams weren't the only adversaries present at New Orleans’ Caesars Superdome. President Donald Trump and musician Taylor Swift were also in attendance, as was expected.

Trump, the 2024 TIME Person of the Year, and Swift, who received TIME’s Person of the Year title in 2023, have a complicated past. Both parties have called one another out over opposing political views and actions. After staying away from publicly commenting on politics during the beginning of her career, Swift endorsed a Democratic candidate in the U.S. Senate election in Tennessee in 2018. Trump publicly responded to Swift’s endorsement, and various comments have been made by both sides since.

Indeed, this tense relationship became a focus of the night, as a moment when Swift appeared to be booed—perhaps by Eagles fans opposing her boyfriend Travis Kelce's Chiefs—was widely shared by Trump supporters online, and even by Trump himself on his social media platform Truth Social.

In light of both Trump and Swift attending the Super Bowl, here’s a look back at their tense history.

October 2018: Trump responds to Swift’s endorsement of Democratic candidate
Though Swift had, prior to this, stayed away from political endorsements, she decided in 2018 to voice her support for Democratic senatorial candidate Phil Bredesen over Republican candidate Blackburn. Swift said Blackburn's voting record in Congress “appalls and terrifies" her.

At the White House a few days later, Trump was asked about the endorsement by reporters.
August 2019: Swift says Trump thinks he’s in an “autocracy”
In an interview with the Guardian, Swift publicly criticized Trump after not endorsing a candidate during the 2016 election. When asked about the Trump Administration by the publication, she said: “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 also told the outlet that she felt “really remorseful for not saying anything” during the 2016 election between Trump and Democratic candidate Hillary Clinton.


January 2020: Swift reveals more in her Miss Americana documentary
In her 2020 Netflix documentary, Miss Americana, Swift took fans behind the scenes of her decision to endorse Tennessee Democratic candidate Bredesen in his Senate race against Republican candidate Blackburn, which was ultimately won by Blackburn.

In the documentary, Swift refers to Blackburn as “Trump in a wig.”

May 29, 2020: Swift tells Trump “we will vote you out”
Swift took a strong stand against the President in the midst of the protests after the killing of George Floyd. Trump posted on X (formerly Twitter), warning protesters in Minnesota that “when the looting starts, the shooting starts.” Trump’s post was then flagged by Twitter—two years before the platform was bought by Trump supporter and DOGE leader Elon Musk—for “glorifying violence.”

Swift then took to the same social media platform to address Trump directly. “After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence?” she wrote. “‘When the looting starts the shooting starts’??? We will vote you out in November. @realdonaldtrump.”