Taylor Swift, a secret note and a problematic man.

In surprising celebrity news, Taylor Swift has recently forged a strange new alliance. With whom you might ask? It's with Barstool Sports founder, David Portnoy. And it's safe to say, the world was not expecting it. 

After recently attending the Eras Tour in Miami, Portnoy took to his Instagram to share his thoughts on the evening. 

"It was spectacular... just an amazing night," he said in an Instagram video, "I did get in the VIP section, which was amazing." 

He then took out a handwritten letter from Swift, which Swift's brother, Austin Swift, had personally given him while attending the concert. The envelope had Dave written across the front with a hand-drawn star next to it. 

"Dave, I'm so happy to have you at the show tonight! I wanted to say thank you for always being so supportive, so loyal, and for having my back when a lot of people didn't. I hope you have a blast tonight!!" Swift wrote in the letter. 

Many fans were baffled by the interaction, while others that know a little bit more about Portnoy, have called it problematic.

So who is David Portnoy? And why has this recent exchange got the internet in a twist? 

Listen to The Spill's episode about Taylor Swift and Dave Portnoy. Article continues below.

Who is David Portnoy?

David Portnoy is an American businessman and social media personality who is best known for founding Barstool Sports, a digital media company that covers sports and pop-culture. 

His company offers a range of audio, video and written content and has been described as 'the Bible of bro culture'. 

While Barstool Sports has found immense success over the years, Portnoy has also been the centre of various controversies. But more about that later. 

David Portnoy attends Game Four of the 2024 NBA Finals. Image: Getty

David Portnoy has been a long term fan of Swift. 

Portnoy has been a loud and proud Swiftie for many years now, publicly defending her during many of her scandals. 

Does everyone remember the Kanye West and Taylor Swift feud? To jog your memory, in 2016, West released his song 'Famous' which included the lyric, "I feel like me and Taylor might still have sex. Why? I made that b*tch famous." 

Following the song's release, West claimed that Swift gave him permission to use the lyrics, a claim Swift denied. In defence of West, his then-wife Kim Kardashian released secretly-filmed footage of Swift on the phone with West, where they are heard discussing the 'might still have sex' line. 

Swift was quick to respond to the video, sharing a note to Instagram that read, "Where is the video of Kanye telling me he was going to call me 'that b*tch' in his song? It doesn't exist because it never happened. You don't get to control someone's emotional response to being called 'that b*tch' in front of the entire world." 

But, at that point no one was listening and #TaylorSwiftIsOverParty started trending on Twitter, signalling the start of her public cancellation.

Four years after the incident, Portnoy went on the Chicks in the Office podcast and shared his thoughts on the feud, condemning Kardashian and West for lying. 

"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 said. 

"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 [it] started with Kanye when he interrupted her acceptance speech."

Watch Kayne West interrupt Taylor Swift at the 2009 MTV VMAs. Article continues after video.

Portnoy has gone as far as to make Barstool Sports merchandise in support of Swift and called out those who have wronged her. One shirt read, "All You're Ever Gonna Be Is Mean And A Liar And Pathetic" and named Kardashian, West, and Scooter Braun. 

More recently, in 2023, Portnoy called out Swift's bestie, Brittany Mahomes when her and Patrick Mahomes featured in a Skims campaign. Portnoy took to Twitter and expressed his frustration at Mahomes' lack of loyalty to Swift. 

"BRITTANY MAHOLMES IS TRASH!!! WAY TO STAB TAYLOR RIGHT IN THE BACK AFTER SHE WELCOMED YOU INTO HER WORLD," he wrote. 

BRITTANY MAHOLMES IS TRASH!!! WAY TO STAB TAYLOR RIGHT IN THE BACK AFTER SHE WELCOMED YOU INTO HER WORLD https://t.co/ovuDsx5wYC

— Dave Portnoy (@stoolpresidente) November 9, 2023

His undying support for Swift continued into 2024, when she made an official announcement of her support for presidential candidate Kamala Harris. Portnoy, a Trump supporter himself, defended Swift's choice and maintained that "people can vote for whoever they want in this country." 

Portnoy's problematic past. 

Here's where the Swift and Portnoy interaction has the internet divided. 

Portnoy is no stranger to controversy and has had his fair share of problematic allegations throughout the years. 

In 2022, a series of sexual assault allegations against Portnoy by several women were reported by Business Insider. Business Insider claimed that the publication spoke to more than two dozen women, including women as young as 19, who reported explicit online exchanges with Portnoy. Several women also accused Portnoy of choking and filming them without their consent. 

"It was so rough I felt like I was being raped," one alleged victim claimed. 

Dave Portnoy visits Faction Talk at SiriusXM Studios in 2017. Image: Getty

Another woman spoke of being suicidal after an alleged encounter, but was too scared to speak up in fear of Portnoy's retaliation. 

"I know how he is when someone goes after him. I thought he would say something in public, or share videos of me," one woman said. 

Portnoy responded to the allegations via a video on X at the time and denied the claims, calling the article "a hit piece." 

Prior to these allegations, Portnoy had also come under fire for making inappropriate jokes about rape. 

In a 2010 post on his website, Portnoy wrote, "I never condone rape, but if you're size six and you're wearing skinny jeans, you kind of deserve to be raped."

In 2017, Portnoy once again found himself embroiled in controversy when ESPN's Sam Ponder called him out for an article he had written about her in 2014.

In the article, Portnoy called Ponder a "slut" and a "super-prude" and claimed that she had a "job where the #1 requirement is you make men hard."

In light of Portnoy's problematic history, many fans were concerned about Swift's decision to publicly align herself with him.

Swift has historically been an outspoken advocate of women's rights and has previously fought her own legal case against a radio DJ, named David Mueller, who groped her.

In her documentary Miss Americana, Swift said that many people questioned the validity of her claim because she hadn't immediately reacted when the man groped her while they were taking a photo.

She says she was asked, "Why didn't you scream? Why didn't you react quicker? Why didn't you stand further away from him?

For reference, while she remained composed for the photo, her security team were immediately informed and they confronted the DJ. They also informed his workplace, which resulted in him being fired. He sued Swift for defamation, seeking $3 million in damages, and she countersued him for just $1, and won.

She said of the experience, "I was so angry. I was angry that I had to be there, I was angry that this happens to women, I was angry that all the details had been twisted."

Fans online felt that her own experience of fighting to be believed may have made her second guess a friendship with Portnoy.

"Taylor Swift writing Dave Portnoy a thank you note is so utterly bizarre in every way, I'm sorry," one user wrote on X.

"Taylor apparently wrote Dave Portnoy a letter and woah, I never thought I'd see such a huge swing and miss from her. like? What is the thinking here????" another added.

Swift has not addressed the online messages, although other fans have come to her defence.

"I love how hard Dave Portnoy loves Taylor Swift," a fan wrote.

Perhaps, Swift never thought the contents of that letter, handed privately to Portnoy, would be made public.

Feature image: Getty.