Donald Trump Questioned If ‘Unusually Beautiful’ Taylor Swift Is ‘Legitimately Liberal’ or Not

Last November, the editor of Variety, Ramin Setoodeh, interviewed the former US president and recently convicted felon for a book titled Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass. According to an extract provided by Variety, the book contains the sentiments of Donald Trump over the 'unusually beautiful' Taylor Swift. 

In November 2023, Setoodeh inquired about Trump's opinions on Swift, and he was quite complimentary of her looks. He said at the time, "I think she’s beautiful — very beautiful! I find her very beautiful. I think she’s liberal. She probably doesn’t like Trump. I hear she’s very talented. I think she’s very beautiful, actually — unusually beautiful!" When asked about her music in particular, Trump said, "Don't know it well." He continued by wondering whether the pop sensation is indeed a liberal: "She is liberal, or is that just an act? She’s legitimately liberal? It’s not an act? It surprises me that a country star can be successful being liberal."

In response to Setoodeh's observation that Swift is now more than just a country musician, Trump said: "Garth Brooks is liberal. Explain that! How does it happen? But he’s liberal. It’s one of those things..." Swift avoided politics for the most part during her career. That all changed in 2018, when she lent her support to the Democratic candidate for the Senate from Tennessee, Phil Bredesen, who was running against the Republican incumbent, Marsha Blackburn. "Due to several events in my life and in the world in the past two years, I feel very differently about that now," Swift said in a long Instagram post, explaining why she had been reluctant to publicly voice her political ideas.

She further added, "I always have and always will cast my vote based on which candidate will protect and fight for the human rights I believe we all deserve in this country." In her 2020 documentary Miss Americana, Swift discussed her resolve to openly support Democrats more, revealing misgivings over her silence against Trump in 2016. However, Bredesen was defeated in the red state by Blackburn. The members of Swift's staff warned her in the documentary that the public would misunderstand her support of Bredesen as a criticism of Trump.

While this interview did take place in November 2023, it was far from Trump's sole recent mention of Swift. In a September 2023 interview with the Daily Caller, he made fun of the star's relationship with Travis Kelce, a tight end for the Kansas City Chiefs. He said at the time, "I wish the best for both of them. I hope they enjoy their life, maybe together, maybe not — most likely not." Subsequently, he boasted on Truth Social about having signed the Music Modernization Act while in office.

In a February piece that alluded to Swift's backing of the incumbent president's 2020 presidential campaign, Trump wrote, "Joe Biden didn’t do anything for Taylor, and never will. 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."