The founder of Barstool Sports, Dave Portnoy, has publicly pledged to retain his Bitcoin investment, even if it were to plummet to zero. He recently disclosed that he is facing millions in losses on a position he bought when Bitcoin was close to $100,000.
Portnoy's history with Bitcoin trading has been tumultuous, largely characterized by poor timing. In an interview with Fox Business host Stuart Varney, he revealed that his previous experiences with buying high and selling prematurely during market peaks have influenced his decision not to divest in the current downturn.
A Painful Investment History
During the conversation, Portnoy expressed regret over his earlier Bitcoin trades, admitting to a significant loss when he sold during a downturn in 2021, just before the cryptocurrency sharply rebounded. He pointed out that every time he tried to exit his position, Bitcoin would rally soon after, solidifying his resolve to hold onto his investment this time around.
Despite Bitcoin's steep decline from its October peak of $126,080 to approximately $62,162, Portnoy remains steadfast. "Bitcoin and crypto are making me sad," he tweeted on June 4, 2026, reflecting on his investments' performance.
Contrasting Views on Bitcoin's Future
While Portnoy is determined to hold, opinions on Bitcoin's future trajectory are sharply divided within the investment community. Notably, Robert Kiyosaki, the author of Rich Dad Poor Dad, recently claimed that Ethereum could soar to $95,000 by mid-2027, suggesting a global financial crisis could trigger such a rise. He also forecasted that Bitcoin could reach $750,000 in that scenario.
Conversely, Matt Hougan, the Chief Investment Officer at Bitwise, has stated that Bitcoin might be nearing the end of its correction phase, following a reduction in excess leverage associated with STRC. He anticipates a potential resurgence in the Bitcoin market as early as fall, cautioning, however, that pinpointing the exact market bottom is inherently unpredictable.
As the cryptocurrency market continues to evolve, it remains to be seen whether Portnoy's strategy of holding will pay off or if the cryptos will continue their downward trend.
