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Lately, things may not be so favorable for Barstool Sports’ CEO Dave Portnoy. He has been on a losing spree for his misplaced wagers. Dave Portnoy was exuding confidence ahead of the match between the Buffalo Bills and the Dallas Cowboys. It took the same downhill road as the Cowboys, on whom Portnoy had put his belief and money, faced defeat. However, every tumultuous event has a silver lining, if one keenly looks for it.

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And, for Portnoy, who could be it more than Taylor Swift? The pop star seemed to have unknowingly given Portnoy the much-needed boost up as an overjoyed Portnoy took to social media to share his excitement.

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“worst day” of Dave Portnoy lightened up swiftly

It was indeed disappointing to watch the Dallas Cowboys face a cruel loss against the Buffalo Bills. Cowboys are known for their undefeated record at home. However, it was not the same recently. And, given that Portnoy placed his bets on the Cowboys, it was disheartening for him. In the wake of this stunning upset, Portnoy also ended up losing his t-shirt. Marked by two losses, he took to his X handle, to reveal his anguish. Amidst the intense showdown, he penned, “I had worst day gambling today. Lost my shirt.”

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However, on the better side of it, Taylor Swift was in the audience for the match. While the popstar’s presence is reason enough for Dave Portnoy to be elated, there was more to add to it. He wrote in his tweet, “Made up for it by @taylorswift13 drinking @nooners when the cameras aren’t on.”

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Despite the gloominess, the fact that Taylor Swift was drinking the beverages from his brand, “Nooners,” cheered him up. He spotted the Nooners can be placed in front of Swift, which captivated his attention. But that did not stop him from venting his frustration for the Cowboys.

Portnoy slams the “old Cowboys”

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Portnoy was extensively put down by Cowboys performance. In another tweet, he wrote, “I was so confident the Bills would beat the Cowboys I switched my bet to Dallas only to watch the same old Cowboys. Dak sucks.  Stupid Penalties.   Dumb coaching.  They suck.  Kick them outta the league.”

Read More: “What the Hell Was This”: Dave Portnoy in Denial After Losing Thousands Over Vikings vs Bengals Bet

This loss of Dave Portnoy is the fresh addition to his rather disappointing betting record after her recent loss of thousands for the Minnesota Vikings. The Dallas Cowboys were handed out a 31-10 loss in the Sunday night football by the Buffalo Bills.

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Shivangi Agrawal

1,745 Articles

Shivangi Agrawal is a Senior NFL Writer at EssentiallySports. She focuses on uncovering NFL stories that resonate with fans, particularly during game-day coverage. Shivangi blends traditional football analysis with entertainment angles and off-season narratives, delivering engaging, journalistically grounded content that goes beyond the field. With eight years of experience in journalism, she has contributed to articles, features, and audience-focused reporting, combining strong storytelling skills with a deep understanding of the NFL and its broader culture.

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Bhujaya Ray Chowdhury

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