Taylor Swift is known for her kindness and generosity, but she is also strong-willed and unafraid to speak her mind. She has passionately advocated for LGBTQ+ rights, gender equality, and racial justice, using her platform to address social issues. While her activism has earned admiration, it has also sparked criticism, including public clashes with Donald Trump. Despite opposition, Swift remains steadfast in her beliefs, proving herself a powerful voice in both the music industry and the political sphere.

Despite Donald Trump's biting comments, Taylor Swift remains unafraid, diving into politics and voicing her opinions, fueled by years-long feud that shows no signs of ending. Here is a timeline of it.

In 2012 August 1, long before Donald Trump ventured into politics, he claimed to have taken a photo with Taylor Swift. However, instead of sharing the alleged image, he merely posted on X, "Thanks for the beautiful picture— you are fantastic!"

The existence of this supposed photo remained unverified, as it never surfaced publicly. At the time, Trump was a well-known reality TV mogul, while Swift, still focused on country music, was preparing for the release of her album 'Red'.

On October 26- 2012, Donald Trump shared his thoughts on Taylor Swift’s breakup with Conor Kennedy, tweeting, “Re: Taylor and Conor–great news for Taylor!” His interest in celebrity relationships was evident as he commented on the young couple’s split.

Despite allegedly being preoccupied with his efforts to obtain President Obama’s college transcripts, he still took a moment to share his perspective on Swift’s personal life.

Donald Trump acknowledged Taylor Swift's accomplishment of securing a prominent presenting position with the Recording Academy on October 30, 2012.

Trump tweeted on X about how excited he was to hear that she would co-host the Grammy nominations special and conveyed his enthusiasm. He stated, "Taylor is terrific!"

After years of avoiding political discussions, Taylor Swift took a stand ahead of the 2018 midterms. She later described Blackburn as "Trump in a wig" in her Miss Americana documentary, criticizing her stance on gender equality.

In response, then-President Donald Trump dismissed Swift’s political stance, stating she knew little about Blackburn. Addressing reporters at the White House, he remarked, "I like Taylor’s music about 25% less now, okay?"

Public interest in Taylor Swift increased when she began dating Kansas City Chiefs tight end Travis Kelce in the fall of 2023, and even Donald Trump shared his thoughts. He stated, "I wish the best for both of them. I hope they enjoy their life, maybe together, maybe not — most likely not," in an interview with Daily Caller on September 23, 2023.

The rumored relationship quickly gained popularity since then, creating what is now known as a romcom-esque love story.

Donald Trump made audacious boasts about its performance on November 2, 2023, telling an audience at a rally in Houston that it had shot to the top of the charts.

"It beat Taylor Swift, it beat Miley Cyrus, who was number one and two," he claimed, adding that their songs were pushed down for a significant period. However, Billboard's rankings showed otherwise.

Before Joe Biden withdrew from the 2024 presidential race, Donald Trump took to Truth Social to question Taylor Swift’s potential support for the then-president’s re-election. He wrote, “There’s no way" the pop star could endorse Joe Biden.

Trump argued that Biden had contributed nothing to her career and implied that supporting him would be an act of disloyalty, despite Swift’s previous endorsement of the Democrat.

In the June 2024 book Apprentice in Wonderland, Donald Trump shared his views on Taylor Swift, commending her appearance.

Despite this, he repeatedly complimented her looks, remarking, "I think she’s very beautiful, actually—unusually beautiful!" His comments, featured in an interview with author Ramin Setoodeh, highlighted both his admiration for Swift’s beauty and his assumption about her political stance.

In 2024, Donald Trump shared a post on Truth Social featuring digitally altered images of women wearing "Swifties for Trump" t-shirts and a manipulated picture of Taylor Swift with text suggesting she supported his campaign.

The original creator of that post clarified that it was meant as a joke and believed Trump understood it. 

On September 11, 2024, Taylor Swift endorsed Kamala Harris for president, calling her a "warrior" and urging fans to vote wisely. She cited Donald Trump’s use of AI-generated images as a key reason for speaking out, stating, “The simplest way to combat misinformation is with the truth.”

In response, Trump dismissed her as "very liberal" and claimed it would hurt her commercially. 

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Trump then redirected attention to Brittany Mahomes, saying, “I like Brittany, I think Brittany’s great.”

Frustrated by Taylor Swift’s endorsement of Kamala Harris, Trump took to Truth Social to vent his anger. In an all-caps post, he wrote, “I HATE TAYLOR SWIFT!” but offered no further explanation. However, Swifties turned the vitriol into a positive situation for Harris. 

While some conservatives online claimed they were done with Swift, Trump’s outburst may have only strengthened her support among Swifties.

Both Donald Trump and Taylor Swift attended the 2025 Super Bowl, marking the first time a sitting president was present at the event. Swift was there to cheer on Travis Kelce as the Chiefs faced off against the Eagles. After Kansas City Chiefs’ crushing Super Bowl loss, when swift's face appeared on the stadium’s big screens, a portion of the crowd reacted with boos.

Wasting no time, Trump took to Truth Social, claiming “She got BOOED out of the Stadium. MAGA is very unforgiving!” Nonetheless, despite his attempts to undermine her, Swift's influence remains strong, showing that their feud is not just political but also a reflection of shifting generational and ideological trends.

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What do you think about Donald Trump's remarks about Taylor Swift and their ongoing feud? Let us know in the comments below.