Taylor Swift is reaching beyond the political aisle, so to speak. After endorsing Kamala Harris as president in 2024, Swift sent a handwritten letter to Barstool Sports founder and owner Dave Portnoy before one of her concerts.

First, a little history lesson – because when Swift is involved, there's always lore. Portnoy has been outspoken about voting for Republican candidate Donald Trump. He is also a huge Swift fan, having declared himself the “King of the Swifties.” That's why many asked him what he thought of Swift when the pop star publicly endorsed Democrat Harris in mid-September.

“I don't care at all. The people of this country can vote for whoever they want. How someone votes will never change my opinion of a person. I vote the other way, but right for everyone,” Portnoy wrote on X in September. The Barstool Sports boss has continued to support Swift and embrace his fan base.

When Portnoy attended Swift's Eras Tour show in Miami on Sunday, he was pleasantly surprised to receive a handwritten letter from Swift. The letter was titled “Dave!” and sealed with a wax seal highlighting Swift's iconic lucky number, 13. The note also appeared to hint at Portnoy's support of Swift following her political endorsement.

“I’m so excited to have you on the show tonight! I wanted to thank you for always being so supportive, so loyal, and for having my back when many others didn't. I hope you have a great time tonight!!” Swift wrote.

Portnoy posted a picture of the letter to the Instagram account for his podcast “BFFs.” “What a gift from @taylorswift to @stoolpresidente at the Eras Tour last night,” the post reads. In another clip, Portnoy described Sunday night's show as “spectacular.”

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