Why can't Donald Trump stop trolling Taylor Swift amid supporting Travis Kelce and the Chiefs?

Donald Trump’s obsession with celebrities is nothing new. Long before politics, he thrived on fame, gossip, and influence, shaping his identity as a pop culture figure. But among all the stars he has fixated on, Taylor Swift stands out. Why? Because she represents everything Trump wants but can’t have—youthful influence, massive cultural power, and a fiercely independent stance against his brand of politics.

Trump has always been obsessed with how famous people react to him. Those who support him—like Kanye West or Kid Rock—gain VIP treatment. But those who reject him seem to live in his head rent-free. When Swift endorsed a Democrat in the 2018 Tennessee Senate race, Trump sniped, “I like her music 25 percent less.” Swift clapped back with a clever merch discount of the same percentage, making it clear she wasn’t intimidated.

In 2020, she doubled down, directly calling Trump out. And in 2024, his frustration reached new heights when she endorsed Kamala Harris, prompting Trump to rage-post, “I HATE TAYLOR SWIFT.” His desperate attempt to fabricate an AI-generated image of Swift endorsing him was not only pathetic but also an indication of how much he wishes he had her influence on his side.

The latest chapter in Trump’s Swift obsession played out at Super Bowl LIX. Both he and Swift were in attendance, sparking speculation about a possible interaction. But when the Jumbotron showed Swift, boos erupted in the stadium. Meanwhile, Trump was reportedly met with cheers. Naturally, he couldn’t resist trolling her. He posted a side-by-side comparison video, letting the footage speak for itself.
Right-wing accounts jumped on the moment. One of them, Libs of TikTok, posted, “Trump gets massive cheers at the Super Bowl while Taylor Swift gets booed. The world is healing!” Trump re-posted it, basking in the perceived victory.

Trump’s fixation on Swift isn’t just about personal pettiness. It’s a calculated move. He knows her cultural impact is enormous, and by attacking her, he rallies his base—who thrive on outrage and anti-celebrity sentiment. The more Swift resists him, the more he uses her name to fuel division and stoke his followers' emotions.
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Swift, on the other hand, has never taken the bait. Her power lies in ignoring his tantrums and continuing to make history—on her terms. And that’s exactly what drives Trump crazy.