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Bitcoin

Dave Portnoy says Bitcoin is the one trade he can't win

Down Millions and Not Selling Barstool Sports founder Dave Portnoy (@stoolpresidente) has once again found himself on the wrong side of a Bitcoin ($BTC) trade, and this time he says he is not

AnonymousCryptoCompass newsroom
July 3, 2026
3 min read
NEWS
Dave Portnoy says Bitcoin is the one trade he can't win
CryptoCompass editorial visual for bitcoin coverage.

Down Millions and Not Selling

Barstool Sports founder Dave Portnoy (@stoolpresidente) has once again found himself on the wrong side of a Bitcoin ($BTC) trade, and this time he says he is not moving. Appearing on Fox Business with Stuart Varney, Portnoy confirmed he is down millions on Bitcoin after it fell more than 50% from its October all-time high of $126,080 to a recent price of around $62,000.

"Yeah, I've got regrets," Portnoy told Varney. "I bought the thing at $100,000, so I mean, right now, I don't know what's going on."

At that level, Bitcoin is down by more than half from its all-time high of about $126,000 reached in October 2025. The decline has been driven by a range of factors. Sentiment took a hit after Strategy, founded by Michael Saylor, sold a portion of its Bitcoin holdings, which triggered hundreds of millions of dollars in liquidations and accelerated the sell-off. Losses were compounded by a stronger-than-expected jobs report that sent Treasury yields higher and pressured risk assets broadly.

A Familiar Story With a Different Ending

"There's nothing I've been wrong about more than Bitcoin," Portnoy told Varney. His track record with the asset is, by his own admission, painful. He recalled first buying roughly $2 million worth of Bitcoin when it traded around $11,000 after a conversation with Cameron and Tyler Winklevoss, only to sell almost immediately because he did not understand their long-term thesis.The decision proved costly as Bitcoin quickly surged, eventually convincing him to re-enter the market at much higher prices.

Portnoy got back in at various higher prices over the following years, building to a peak position of around $15 million before losses brought it down significantly. He also famously panic-sold near a market bottom in 2021, a move he has since described as one of his worst calls.

This time, Portnoy says his approach is different. Despite the continued downward price action, he said he is just holding his ground. "I'll just hold this thing down to $0," he said. "I know if I sell it, it's going to go nuclear again. I'd rather go down with the ship this time."

Portnoy admitted he still struggles to predict the cryptocurrency's moves despite years of following it closely. "I don't know what the hell's going on with it," he said, adding that he intends to keep holding his position even if it continues to fall.

The latest remarks are consistent with a broader pattern. His main psychological anchor, by his own account, remains a conversation with former Twitter CEO Jack Dorsey, who personally convinced him that Bitcoin would inevitably rise to $1 million.

SourcesFox Business: Dave Portnoy reveals impact of Bitcoin crash on wealthDecrypt: Dave Portnoy Says He's Losing Millions as Bitcoin FallsCNBC: Bitcoin cracks $60,000, sinking to lowest level since October 2024