Barstool’s Dave Portnoy Has a Long History as a Taylor Swift Fan: From ‘Eras Tour’ Jacket to Letter

Barstool Sports founder Dave Portnoy has not been shy about sharing his support for Taylor Swift over the years.

The controversial internet personality is a longtime Swiftie who started going viral regarding his support of Swift when it came to her drama with Kim Kardashian and Kanye West.

“I’ve never seen anybody try to suck up like she is to Taylor Swift,” Portnoy said of Kardashian during an October 2023 episode of his “BFFs” podcast. "We all remember what you did with Kanye when you edited the footage and tried to make Taylor seem like a crazy liar.”

Portnoy was, of course, referring to the 2016 drama surrounding West’s song “Famous” in which he apparently called Swift for the OK to use her name in the first verse. Kardashian posted an edited video of the phone call, seemingly making Swift seem complicit. However, Swift was not privy to the full lyrics, including the chorus, “I made that bitch famous,” which was shown in a leaked video of the full phone call years later.

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Portnoy went viral as a Swift fan again one year after his Kardashian rant when Swift wrote him a handwritten letter thanking him for all the support throughout her career.

Keep scrolling for an inside look at Portnoy’s support of Swift:

The Kim Kardashian of It All

Four years after Kardashian first released the video of Swift and West, the full phone call was leaked. Portnoy went on the “Chicks in the Office” podcast at the time to back Swift.

“Basically, everything Taylor Swift has said, which I'm sure you laid out the entire way is the truth and everything that Kim said has basically been a version of a lie or manipulation of the truth,” Portnoy stated during the March 2020 podcast episode. “Taylor Swift is off on her own island minding her own business and keeps getting dragged into their world through no fault of her own — and started with Kanye when he interrupted her acceptance speech.”

The ‘Midnights’ Support

Portnoy was quick to share his favorite songs from Midnights when Swift dropped the record in October 2022.

“I thought it was pretty f---ing good. I am a Taylor Swift fan,” he said on the BFFs podcast at the time. “I’ve been a Taylor Swift fan for a while. I think she’s a genius.”

The ‘Eras Tour’ Jacket

Initially, Portnoy didn’t know if he was going to attend the Eras Tour — let’s not revisit the Ticketmaster debacle — but thanks to a fellow Barstool employee, El Pres went to night one at MetLife in May 2023.

His outfit went viral when it was revealed to be a custom denim jacket featuring all of Swift’s musical eras. Following his time at the concert, Portnoy decided to pass along the jacket to other Swifties. An Instagram account has since been made for the special piece of merch where fans connect over the jacket and share letters of their experience at the concert.

The Barstool Sports Merch

Portnoy made Barstool merch supporting Swift and calling out the singer’s enemies. “All You’re Ever Gonna Be is Mean and a Liar and Pathetic,” the shirt reads, naming Kardashian, West, Scooter Braun and “all Taylor’s ex boyfriends.”

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Calling Out Brittany Mahomes

Portnoy was not happy with Patrick and Brittany Mahomes — who have formed a friendship with Swift because of her relationship with Travis Kelce — worked with Kardashian’s Skims brand.

“I’m on an airplane, and I don’t want to make too much noise, I hope everyone can hear me for this emergency press conference, but when Taylor Swift news strikes, I gotta be there to answer for the Swifties,” he said in a November 2023 TikTok. “We gotta protect Mother. Maybe Brittany Mahomes had her head in the f---ing sand and doesn’t know the history, in which case, she owes Mother and all of us an apology.” (Swift and Brittany, meanwhile, appear to still be close friends.)

‘ThanK you aIMee’

Of course, Portnoy had a lot to say when Swift released this song in April 2024 on her The Tortured Poets Department record.

“I have been at the forefront of this for years, saying [to] the Swifties, we do not forgive, we do not forget,” Portnoy said in the viral video. “She writes a song, Taylor, ‘ThanK you aIMee,’ K-I-M capitalized.”

He continued, “This is Taylor’s masterpiece.”

Swift’s Letter

In October 2024, Portnoy read a handwritten letter that was delivered to him by Swift’s brother, Austin Swift, during a Miami Eras Tour show. He also said that he met Swift’s mom, Andrea Swift, in the VIP tent.

“Dave, I am so happy you are at the show tonight. I wanted to say thank you for always being so supportive, so loyal, for having my back when a lot of people didn’t,” the letter read. “I hope you have a blast tonight. Love, Taylor.”