Bitcoin News: Dave Portnoy, founder of Barstool Sports, disclosed on Fox Business that he is sitting on millions in losses after buying Bitcoin near $100,000, and announced he will hold the position all the way to zero rather than sell again.

The declaration, made on Stuart Varney’s Varney & Co., crystallizes a behavioral pattern that has cost Portnoy heavily across multiple market cycles: buying near local highs, selling before rallies, and re-entering at higher prices.

BTC price peaked above $126,000 in October 2025 before halving to its current level around $62,870, according to CoinDesk data. Portnoy’s latest entry near the $100,000 level puts his unrealized loss at roughly 37% from cost basis, with the peak-to-trough drawdown from his buy point exceeding $60,000 per coin.

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Bitcoin News: The Quote That Defines the Trade

Portnoy did not soften the assessment when speaking to Fox Business host Stuart Varney. “Yeah, I got regrets. I bought the thing for $100,000. There’s nothing I’ve been wrong about more than Bitcoin. Every time I sell it, it goes nuclear. Every time I buy it, it tanks,” he said.

The self-diagnosis is unusually blunt for a public figure with a position still on the books.

“I’m holding. I’ll hold this thing down to zero. I know if I sell it, it’s going to go nuclear again. I’d rather go down with the ship this time.”

Photo: Dave Portnoy

The logic is behavioral rather than analytical: Portnoy is not making a valuation case for Bitcoin; he is reacting to a personal track record of selling before every major rally. His commitment to hold to zero is, in effect, a forced discipline imposed by demonstrated inability to time exits correctly.

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A Multi-Cycle Pattern of Poor Market Timing

Portnoy’s history with Bitcoin reads as a case study in retail FOMO compounding. He first entered in late 2020 with approximately $2 million at around $11,000, then sold almost immediately, a position that would have returned roughly 6x had he held through BTC’s early 2021 run to $60,000.

He subsequently rebuilt exposure at higher prices, with his peak Bitcoin position reportedly reaching around $15 million before market declines cut that substantially.

The latest cycle repeated the same dynamic at a higher dollar magnitude. Portnoy has publicly stated he exhausted most of his available cash, averaging down through the drawdown, and his BTC losses now run into the millions on an unrealized basis. His exact BTC holdings remain undisclosed.

The pattern, buy high, capitulate, re-enter higher, is precisely what distinguishes retail investors who underperform a simple buy-and-hold strategy across cycles.

Market timing failure at Portnoy’s scale illustrates the structural disadvantage most active traders face. Research consistently shows that retail investors who attempt to time entries and exits in volatile assets like Bitcoin generate returns well below passive holders over equivalent periods. The risks that accompany prominent Bitcoin holders who buy in size and then face sustained drawdowns are not unique to Portnoy, but his public commentary makes the behavioral traps unusually visible.