Michael Saylor’s relentless accumulation of Bitcoin continues to grab headlines, but not everyone is cheering. Economist and long-time crypto critic Peter Schiff has issued a stark warning, arguing that Saylor’s Bitcoin-heavy strategy could soon turn from bold to dangerous. Following Strategy’s latest $1.34 billion Bitcoin purchase—adding 13,390 BTC at an average price of $99,856—Schiff says the risk of “huge real losses” is growing, especially if the Bitcoin price begins to slide.

With this latest buy, Strategy now holds a staggering 568,840 BTC, acquired at a total cost of approximately $39.41 billion. This gives the company an average purchase price of around $69,287 per coin. However, Schiff claims that Saylor’s newest investment likely nudged that figure closer to—or even above—$70,000. That’s a problem, Schiff argues, because if Bitcoin falls below that level, unrealized losses may rapidly become realized losses, particularly given the company’s aggressive use of leverage.

Schiff, known for his unwavering skepticism of Bitcoin, isn’t just making a philosophical argument this time. He’s pointing to a concrete financial risk. The issue, he says, is not simply that Bitcoin could fall in price—it’s that Strategy has bought a massive amount of it using borrowed money. “Borrowing billions to hold a volatile asset works great when prices rise,” Schiff explained, “but it gets ugly when they don’t.”

The bigger concern lies with what could happen to Strategy’s own stock, MSTR, if Bitcoin turns south. The company is currently trading at $413.44 with a market capitalization of roughly $113 billion and an enterprise value of $123.18 billion. Notably, over 51% of that enterprise value is directly tied to the value of its Bitcoin holdings. That puts the company in a precarious position: if Bitcoin’s value declines, so does MSTR’s collateral base, raising the risk of margin calls or forced asset sales—scenarios Saylor has repeatedly pledged to avoid.

The dynamic creates a potentially dangerous feedback loop. A decline in Bitcoin’s value could lead to a decline in Strategy’s stock price, which in turn reduces the collateral backing its debt. If lenders get spooked, the company might be forced to liquidate some of its Bitcoin holdings to stabilize the balance sheet. This is the exact scenario Schiff believes could play out if BTC doesn’t continue climbing—and fast.

While Saylor has remained firm in his “buy and hold forever” philosophy, Schiff argues that this unwavering conviction becomes more of a liability the higher the company’s cost basis climbs. “It’s no longer just about belief in Bitcoin,” Schiff warned. “It’s about financial math. You can’t keep buying high and borrowing more without putting your company at real risk.”

Saylor’s confidence in Bitcoin has been unmatched. He’s built Strategy into one of the world’s largest corporate holders of BTC, transforming it from a software company into a de facto Bitcoin fund. But as Schiff points out, that transformation comes with a steep price: extreme exposure to the volatile crypto market. Each new purchase raises the breakeven point—and narrows the margin for error.

Even as Schiff’s comments draw criticism from Bitcoin supporters, the concerns he raises resonate with investors worried about mounting leverage and market unpredictability. The tension between Saylor’s bullish strategy and Schiff’s bearish warnings captures the broader debate around institutional Bitcoin adoption: is it a revolutionary bet or a ticking time bomb?

For now, Strategy insists it has no plans to sell. But as the company increases its exposure, the stakes only grow higher. Schiff’s message is clear: if Bitcoin doesn’t continue its upward trajectory, Strategy may find itself on increasingly shaky ground—no matter how strong Saylor’s conviction remains.