Barstool Sports founder and media personality Dave Portnoy says his long-running love affair with crypto has cost him millions — and he’s not sugarcoating it.
In an interview this week with Fox Business host Stuart Varney, Portnoy admitted he’s taken significant losses on Bitcoin, which has slid from its October all-time high of $126,080 to roughly $62,162 — a fall of more than 50%. “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.” He also tweeted on June 4, 2026: “Bitcoin and crypto are making me sad.”
Portnoy has been an outspoken, if inconsistent, retail trader for years. He acknowledged past mistakes — including panic-selling in 2021, which he described as “fucking paperhanded” — and summed up his experience bluntly: “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.” This time, he says he’s holding: “I’m just holding. I’ll just hold this thing down to $0. I know if I sell it, it’s going to go nuclear again. I’d rather go down with the ship this time.”
Portnoy’s crypto activities have extended well beyond Bitcoin. He has promoted controversial meme coins such as SafeMoon (SFM), publicly campaigned as part of the “Link Marines” backing Chainlink’s LINK token, and last year traded heavily in Solana meme coins. After publicly sharing his wallet — a move that drew accusations of “pumping and dumping” — he embraced JAILSTOOL, a meme token featuring imagery of his face behind bars. Portnoy said at the time he collected the token “as a memory of you bitches crying like little babies.”
That meme push briefly paid off: JAILSTOOL at one point climbed to a market capitalization above $210 million and even earned a listing on centralized exchange Kraken. But the rally fizzled — as of Friday the token trades just above a $1 million market cap, down more than 99.5% from its peak.
Portnoy’s crypto saga is a high-profile example of the volatility and reputational risk that come with retail trading — especially in meme tokens. Whether his latest decision to hold will pay off or compound his losses remains to be seen, but his public, often theatrical involvement continues to draw attention to the unpredictable dynamics of the crypto market.
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