Dave Portnoy, the founder and president of Barstool Sports, has a long history of getting Bitcoin timing wrong. This time, he bought near recent highs and is watching his money disappear. But instead of selling, he is digging in.
In an interview with Fox Business's Stuart Varney, Portnoy confessed he regrets his most recent Bitcoin acquisition. "Yeah, I got regrets, I bought the thing at $100,000," Portnoy said. He bought when the price was near its recent highs.
Since then, Bitcoin has dropped sharply. "I'm losing millions to it," he told Varney.
His situation is painful but not surprising. Portnoy has a pattern of poor timing. Every time he sells, the price later soars.
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Every time he buys, it crashes. "There's nothing I've been wrong about more than Bitcoin," he said. "Every time I sell it, it goes nuclear. Every time I buy it, it tanks."
Portnoy's track record with Bitcoin is well‑documented. He first got involved after discussions with the Winklevoss twins, who co‑founded the Gemini exchange. Since then, his trades have consistently moved opposite to the market's direction.
In 2020, he sold his holdings before a massive rally to new all‑time highs. Then in 2021, he bought near the top of the cycle only to sell during a dip. Now, with his $100,000 purchase, he is once again on the wrong side of the trade. His public commentary often reflects frustration and confusion, making him a relatable figure for many retail investors who have experienced similar whipsaws.
Portnoy's repeated missteps have turned him into a sort of contrarian indicator among crypto traders, with some joking that they should do the opposite of whatever he does. Despite the ridicule, he remains a prominent personality in sports media, and his ongoing Bitcoin saga continues to draw attention from both fans and critics.
But Portnoy admits he has never been able to predict Bitcoin's direction. He told Anthony Pompliano on "The Pomp Podcast" about his history of bad moves. Now, with his latest purchase losing value, Portnoy is stuck in the same cycle.
This time, he is trying a different strategy.
He fears that selling now would cause him to miss a future rebound. That has happened to him before - he sold, and then the price exploded. This time, he is determined to wait.
But Portnoy still has no idea where Bitcoin is headed. "I don't know what the hell's going on with it," he said. He is not making any predictions. He is just holding on, hoping that his luck finally turns.
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