Taylor Swift reaches across the political aisle, so to speak. Following her endorsement of Kamala Harris for president in 2024, Swift sent a handwritten letter to Barstool Sports founder and owner Dave Portnoy prior to one of her concerts.

First, a little history lesson, because when Swift is involved, there’s always lore involved. Portnoy has been outspoken about the fact that he is voting for Republican candidate Donald Trump. He is also such a big fan of Swift that he has declared himself ‘King of the Swifties’. Many therefore asked him what he thought of Swift when the pop star publicly supported the Democratic Harris in mid-September.

“It doesn’t matter to me at all. In this country people can vote for whoever they want. How someone votes will never change my opinion of a person. I vote the other way, but to each their own,” Portnoy wrote on X in September. The head of Barstool Sports has continued to support Swift and embrace his fandom.

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 finished with a wax seal that highlighted Swift’s iconic lucky number, 13. The note also appeared to reference Portnoy’s support of Swift following her political endorsement.

“I’m so glad you’re on the show tonight! I wanted to thank you for always being so helpful and loyal and for standing by me when many people didn’t. I hope you have a great night!!” Swift wrote.

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

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