Economist Peter Schiff predicted on Monday that Michael Saylor‘s Bitcoin (CRYPTO: BTC) bet would become the largest losing trade in history, surpassing JPMorgan’s infamous “London Whale” loss.
Schiff Makes Bold Prediction
Schiff pointed out on X that Saylor’s firm, Strategy Inc. (NASDAQ:MSTR), is already sitting on unrealized losses of over $10 billion on its underlying BTC holdings
“But by the time it’s closed out, Saylor will shatter the record and book the biggest losing trade in history,” Schiff projected.
Schiff highlighted the “London Whale” fiasco as a reference, where a JPMorgan trader made massive, outsized bets in the credit derivatives market, resulting in a loss of more than $6 billion for the bank.
Strategy didn’t immediately return Benzinga’s request for comment.
Will Saylor Ride Out This Challenging Phase?
Strategy holds over 847,363 BTC with an average acquisition cost of $75,651 per coin, while Bitcoin trades around $63,000. The company’s shares have plunged 31% over the week.
Concerns about the Strategy’s financial strength rose dramatically after it disclosed Bitcoin sales earlier in the month, undermining the “never sell” thesis that bullish investors had counted on.
However, Polymarket bettors don’t see any immediate threat to Strategy, pricing in just an 8% chance of the company going bankrupt this year.
Saylor has defended Strategy, arguing that the company has acted as a major source of liquidity and support to Bitcoin during the current bear market, far from being a “systemic risk” as some have alleged.
Price Action: At the time of writing, BTC was exchanging hands at $63,572.30, down 0.66% in the last 24 hours, according to data from Benzinga Pro.
Strategy shares gained 0.77% in after-hours trading after closing 2.73% lower at $109.46 during Monday’s regular trading session.
Benzinga’s Edge Stock Rankings indicate that MSTR has underperformed with a weaker price trend across short-, medium-, and long-term timeframes.

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