ELMONT, NEW YORK – SEPTEMBER 11: Taylor Swift attends the 2024 MTV Video Music Awards at UBS Arena on September 11, 2024 in Elmont, New York. (Photo by Roy Rochlin/Getty Images for MTV)

An unexpected friendship.

Taylor Swift and Barstool Sports are pretty diametrically opposed. They represent two very different demographics, as evidenced by the backlash that Swift has gotten since dating Kansas City Chiefs star Travis Kelce. Dave Portnoy is the founder of Barstool Sports, and not some typically thought to be in the good graces of the pop superstar. And yet, Taylor Swift penned a heartfelt message to Dave Portnoy on October 20. She mailed a handwritten letter to the businessman, thanking him for his unending support.

Dave Portnoy posted photos of the letter after he attended one of Taylor Swift’s concerts. The message is brief, but the sentiment is strong. The pop superstar thanked Portnoy for “always being so supportive, so loyal, and for having my back when a lot of people didn’t.” She also expressed how happy she was to know that Portnoy took the time to attend one of her shows. Dave Portnoy was overwhelmed by the letter and gushed about it on the official Instagram page for the BFFs podcast. “What a gift from @taylorswift to @stoolpresidente at last night’s Eras Tour,” the caption read.

Dave Portnoy Has Defended Taylor Swift Since 2020

The friendship between Taylor Swift and Dave Portnoy actually dates back to 2020. The latter stuck up for Swift during appearance on Barstool’s Chicks In the Office podcast. He felt the pop star had been unfairly maligned by Kanye West and Kim Kardashian. He subsequently praised albums like Midnights and even released a line of Barstool merchandise in Taylor Swift’s honor. Portnoy has even maintained his Swiftie status through The Tortured Poets Department era, which proved to be the toughest pill for most fans to swallow, musically. He dubbed the polarizing album to be Taylor Swift’s “masterpiece.”

Portnoy also stood up for Taylor Swift when she was criticized for not supporting political causes. The singer was subject to widespread scorn for not endorsing Kamala Harris for president. She eventually did so, but the Barstool Sports founder went on Twitter to clarify that political affiliation does not matter to him. “As the king of the Swifties people are asking me what I think of her Kamala endorsement,” he said. “I don’t care at all. People can vote for whoever they want in this country. How somebody votes will never change my opinion of a person. I’m voting the other way but to each their own.” Some friendships really do endure.