Dave Portnoy of Barstool Sports Has a Longstanding History as a Taylor Swift Enthusiast: From ‘Eras Tour’ Jacket to Letter

Dave Portnoy: The Unwavering Swiftie

Imagine waking up and scrolling through your feed – just to stumble upon something unexpected. That’s how it often feels when Dave Portnoy, the Barstool Sports founder, shares his latest musings. His support for Taylor Swift has never been hidden. This outspoken internet personality turned heads with his vocal stance during her ongoing drama with Kim Kardashian and Kanye West. And, well, perhaps it’s fair to say he’s one of the most vocal Swifties out there.

Rewind to October 2023, when Portnoy took to his “BFFs” podcast, calling out Kardashian’s alleged attempts to curry favor with Swift. You can almost picture him rolling his eyes as he recalls the infamous 2016 incident – where an edited clip of a phone call seemed to paint Swift in a questionable light. Of course, time and a leaked full video shifted public perception, highlighting the complexities behind West’s song “Famous.” It turns out Swift was never fully informed about certain lyrics that sparked so much chatter. If you’re curious about those details, check out the BBC’s coverage on the drama.

The conversation didn’t end there. A year later, Portnoy found himself in another viral moment when Swift penned him a handwritten note thanking him for his unyielding support. Just imagine receiving such a note from someone you admire-must’ve been quite something.

Fast forward to MetLife in May 2023. Portnoy attended one of Swift’s concerts thanks to a colleague’s assistance-ticket drama notwithstanding. His custom denim jacket adorned with Swift’s musical eras became a sensation. Interestingly, he even created an Instagram account dedicated to this jacket, encouraging fans to share stories and connect over their shared experiences at her shows.

In true Portnoy fashion, he launched Barstool merch that cheekily called out some of Swift’s known adversaries like Scooter Braun. The shirt’s bold words spoke volumes: “All You’re Ever Gonna Be is Mean and a Liar and Pathetic.” Yet, despite the fiery merchandise, Portnoy’s support remains steadfast and genuine.

A curious episode unfolded-again capturing headlines-when Patrick and Brittany Mahomes cozied up with Kardashian’s Skims brand. On TikTok, Portnoy held what he dubbed an “emergency press conference,” urging everyone to stand by “Mother” (his term for Swift). It wasn’t just a rant; it was like watching someone defend a family member.

And then came April 2024 – as Portnoy waxed lyrical over Swift’s latest track. His enthusiasm was palpable in a viral video where he declared it her “masterpiece.” It’s almost charming to witness such genuine admiration.

A May 2025 appearance on the “Club Shay Shay” podcast offered more insights into why Portnoy defends Swift so fervently. He minced no words describing Kanye as a divisive figure who perhaps gets undue leniency from others. Reflecting on events like the notorious 2009 VMAs incident-a mix-up as Grammys on his part-Portnoy’s loyalty seems rooted in a belief that the young artist faced unwarranted hostility back then.

You know, for someone like me who occasionally loses track of celebrity news, these events around Dave Portnoy and Taylor Swift remind me that some stories just keep evolving. Perhaps it’s those little bits of humanity-handwritten notes, concert outings-that keep us engaged in their narratives.

For more context, see this BBC Entertainment overview.