Barstool Founder Dave Portnoy Defies Market Crash to Maintain Major Cryptocurrency Investments
New York, Sunday, 7 June 2026.
Barstool Sports founder Dave Portnoy refuses to sell his cryptocurrency despite multi-million dollar losses in June 2026, holding out for a predicted one-million-dollar Bitcoin valuation.
A Multimillion-Dollar Paper Loss
On June 4, 2026, Dave Portnoy, the outspoken founder of Barstool Sports, took to social media to confirm that his cryptocurrency portfolio is deeply in the red [1][2][3]. Portnoy, who has previously described his relationship with digital assets as being akin to mixing “oil and water,” admitted to sustaining multi-million-dollar paper losses [1][2]. The media entrepreneur lamented that he has “not made a cent in crypto” and has instead “gotten whacked” by the recent market downturn [3]. A significant portion of this financial sting stems from his position in XRP, which he acquired in late January 2026 near a local peak of approximately $1.70 [1][2]. By the time of his June 4 announcement, the digital asset had plummeted to roughly $1.17 [2][3].
The Strategy Misstep and Market Contagion
Portnoy’s market woes were further compounded by an ill-timed foray into traditional equities tied to the crypto sector [2]. On May 27, 2026, he purchased shares of Strategy (Nasdaq: MSTR), the largest corporate holder of Bitcoin [2][3]. Unfortunately for Portnoy, this entry point preceded a perfect storm in the markets [2]. Within roughly a week of his purchase, the company’s stock price tumbled by an additional 20 percent [2].
Diamond Hands and the Million-Dollar Prophecy
Despite the cascading losses across his portfolio, Portnoy remains steadfast in his refusal to liquidate his positions [1][3]. Drawing parallels to his betting habits at the Saratoga racetrack, he views the current market crash as an “excellent sale,” adopting the classic contrarian mantra of buying when there is “blood on the streets” [2][3]. However, Portnoy candidly admitted that he has entirely exhausted his “free cash” reserves trying to buy the dip, leaving him without the dry powder needed to capitalize on these lower valuations [1][2][3].