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Barstool Sports founder Dave Portnoy, known for his eccentric takes on the crypto market, has once again confirmed his unofficial status as the person with the worst timing in the industry after admitting to multimillion-dollar losses on his key positions.
In a recent social media address, Portnoy publicly confirmed that he owns a ton of Bitcoin and a substantial amount of $XRP, stressing that amid the current prolonged nosedive, his net losses are already measured in millions of dollars.
Bitcoin and crypto are making me sad.
— Dave Portnoy (@stoolpresidente) June 4, 2026
Moreover, according to the businessman, he has completely exhausted his free cash during the intermediate stages of the decline, effectively losing the ability to defend his portfolio.
'Me and crypto are oil and water': Inside Dave Portnoy's crypto tactics
The most painful hit apparently came from his $XRP position, which Portnoy entered near a local peak in late January 2026 at around $1.70, according to available data, while at the time of his statement the exchange price had already fallen to $1.17.
At the same time, his massive Bitcoin position is also under severe selling pressure, with the asset holding near the psychological level of $63,000. His attempt to buy the local bottom has turned into a prolonged confrontation with the trend, as the charts kept falling faster than new funds could appear.
In his statement, the investor directly complained about the pointlessness of such a strategy, when a person continues spending money on a falling asset while free cash simply runs out, adding that his relationship with cryptocurrency still resembles an attempt to mix water with oil.
$1 million Bitcoin prophecy from Jack Dorsey
The final blow in this chain of failures was his bet on shares of the largest Bitcoin treasury firm, Strategy (MSTR), which turned into a perfect storm for the investor. If Portnoy did indeed enter Strategy shares about a week ago, then in that short period their price managed to fall by another 20%.
The decline was worsened by a historic precedent, as just days ago Michael Saylor's company broke its long-standing "never sell" doctrine and sold 32 BTC from its reserve for the first time in the last three years to pay dividends.
Despite openly panicked sentiment and polarized opinions across social media, Portnoy announced that he intends to show nerves of steel and hold his positions without locking in the loss. His main psychological anchor remains an old conversation with former Twitter CEO Jack Dorsey, who once personally convinced Dave that Bitcoin would inevitably rise to $1 million.
Drawing parallels between the current chaos on exchanges and his bets at the Saratoga racetrack, Portnoy summed up that the current crash is an excellent sale, but only those players who, unlike him, still have dry powder left will be able to take advantage of it.