In his delusional mind, former President Donald Trump has seemed to believe that Taylor Swift might endorse his presidency, claiming that he’s “made her so much money” and thinking that because she once made country music, she’d have to vote Republican.
But no, since 2018, the Eras Tour pop star has been adamant in supporting Democratic causes. And most recently, she endorsed Vice President Kamala Harris and Gov. Tim Walz in their run for president and VP in the 2024 election following Trump’s failed debate against Harris.
“I’m voting for @kamalaharris because she fights for the rights and causes I believe need a warrior to champion them,” Swift wrote in her endorsement.
Over the years, she’s slammed Trump over his handling of Black Lives Matter protests, his attempt to dismantle the U.S. Postal Service, and most recently, his shameless reposts of artificial intelligence-generated images of Swift endorsing him for president.
Here’s a breakdown of every time Swift and Trump have spoken out about each other over the last few years. It is not a love story.
Oct. 2018 — Trump says he likes Swift’s music ‘about 25% less’ after she endorsed a Democrat
Ahead of the midterm elections in 2018, Swift voiced her support for Democratic Senate candidate Phil Bredesen over Republican Marsha Blackburn in Tennessee. The then-president fielded a question on Swift’s stance outside of the White House.
“I’m sure Taylor Swift knows nothing, and doesn’t know anything about [Blackburn],” Trump said, adding, “I like Taylor’s music about 25 percent less now, OK?”
Trump also defended Blackburn’s performance, saying she is “doing a very good job” and is a “tremendous woman.”
Aug. 2019 – Swift slams Trump: ‘He thinks this is an autocracy’
In an interview with The Guardian, Swift criticized the then-president for his approach to abortion rights and his presidency overall.
“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,” Swift said of Trump. She also described the political climate in the country as “gaslighting the American public into being like, ‘If you hate the president, you hate America.’”
Jan. 2020 — Swift regrets not opposing Trump publicly
In her Miss Americana documentary, Swift slammed Sen. Blackburn as “Trump in a wig” and was seen as she discussed with her team whether she’d vocally support Democrats in the 2018 midterm election, saying she regretted not speaking against Trump in the 2016 election.
“I can’t see another commercial [with] her disguising these policies behind the words ‘Tennessee Christian values.’ I live in Tennessee. I am Christian. That’s not what we stand for,” Swift said in the documentary, holding back tears about not opposing Trump before. “But I can’t change that. … I need to be on the right side of history. … Dad, I need you to forgive me for doing it, because I’m doing it.”
May 2020 – Swift vows to ‘vote you out’ in November
Tensions in the country were high following the murder of George Floyd by a Minneapolis police officer. Swift, at the time, came out in support of the Black Lives Matter movement, even donating to the NAACP.
She also criticized Trump’s threats of violent crackdowns on the peaceful protests. “After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence?” Swift wrote on X. “‘When the looting starts the shooting starts’??? We will vote you out in November.”
Aug. 2020 — Swift slams Trump ‘dismantling of USPS’ and his ‘ineffective leadership’
Swift was not happy with Trump’s attempt to mess with the U.S. Postal Service amid voting during the 2020 Covid-19 pandemic.
“Trump’s calculated dismantling of USPS proves one thing clearly: He is WELL AWARE that we do not want him as our president,” Swift tweeted. “He’s chosen to blatantly cheat and put millions of Americans’ lives at risk in an effort to hold on to power.”
“Donald Trump’s ineffective leadership gravely worsened the crisis that we are in and he is now taking advantage of it to subvert and destroy our right to vote and vote safely,” she added.
Oct. 2020 — Taylor endorses Joe Biden and Kamala Harris
Swift appeared on the cover of V Magazine in the fall of 2020, and said we needed to “elect a president who recognizes that people of color deserve to feel safe and represented,” referring to Trump’s handling of the Black Lives Matter movement.
“I will proudly vote for Joe Biden and Kamala Harris in this year’s presidential election,” she said. “Under their leadership, I believe America has a chance to start the healing process it so desperately needs.”
Feb. 2024 — Trump Says Swift won’t endorse Biden because ‘I made her so much money’
Trump seemed to believe he was in Swift’s good graces after signing copyright reform legislation that streamlined how rights-holders get paid when their music plays on streaming services.
“I signed and was responsible for the Music Modernization Act for Taylor Swift and all other Musical Artists,” Trump wrote on Truth Social in February 2024. “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,” he added.
June 2024 — Trump calls Swift ‘unusually beautiful’ but ‘liberal’ in new book
In a book titled Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, Trump shared his thoughts on Swift, calling her “very beautiful” way too many times.
“I think she’s beautiful — very beautiful! I find her very beautiful,” he told book author Ramin Setoodeh. “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!”
“She is liberal, or is that just an act?” he asked Setoodeh, per Variety. “She’s legitimately liberal? It’s not an act? It surprises me that a country star can be successful being liberal.”
June 2024 — Trump questions why Swift would endorse Biden
Trump visited Capitol Hill and spent time complaining about Swift and how she hadn’t endorsed him. “Why would she endorse this dope,” Trump wondered, per CNN. “He doesn’t know how to get off a stage.”
Aug. 2024 — Trump shares AI-generated ‘Swifties for Trump’
On Truth Social in mid-August 2024, Trump shared a collage of screen grabs and photos of a supposed “Swifties for Trump” movement. Two of the images were legit, showing Trump supporter Jenna Piwowarczyk wearing a “Swifties for Trump” shirt at a recent rally in Wisconsin. However, several others showed Swift dressed as Uncle Sam with the caption, “Taylor wants you to vote for Donald Trump.”
Trump shared the images on his account, captioning the collage, “I accept!”
When Fox Business asked him whether he was worried that Swift would sue him about the images, Trump responded: “I don’t know anything about them other than somebody else generated them. I didn’t generate them.”
“These were all made up by other people. AI is always very dangerous in that way,” he added.
Sept. 10, 2024 — Swift endorses Kamala Harris for president following the debate
Shortly after the debate between Harris and Trump ended, Swift announced her endorsement of Harris, calling out Trump and his campaign for circulating AI-generated images suggesting she supported the former president.
“Recently I was made aware that AI of ‘me’ falsely endorsing Donald Trump’s presidential run was posted to his site. It really conjured up my fears around AI, and the dangers of spreading misinformation,” Swift wrote in her endorsement. “It brought me to the conclusion that I need to be very transparent about my actual plans for this election as a voter. The simplest way to combat misinformation is with the truth.”
Sept. 11, 2024 — Trump says Swift will ‘pay a price’ for endorsing Harris
Trump called into Fox News the morning after Swift’s endorsement and said he was “not a Taylor Swift fan.” In fact, he said he “actually likes Mrs. Mahomes much better,” referring to the fact that Brittany Mahomes, wife of Kansas City Chiefs quarterback Patrick Mahomes, had liked pro-Trump posts on social media.
“I was not a Taylor Swift fan,” Trump said. “It was just a question of time. You couldn’t possibly endorse Biden. But 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.”
