Michael Saylor just dropped another $1.34 billion on Bitcoin (BTC), adding 13,390 BTC at an average of about $99,856 per coin. That brings Strategy’s total to 568,840 BTC, bought for roughly $39.41 billion, with an average cost of $69,287. Thus, it is the same playbook as almost every Monday - buy more, hold longer. But Peter Schiff is not buying the logic as probably the most vocal cryptocurrency critic calling out what he sees as the obvious problem - if the next move in Bitcoin's price is down, Strategy's position could start cracking fast. According to Schiff, Saylor’s latest buy likely pushes the company's average cost above $70,000. If Bitcoin drops below that, unrealized losses could turn real - especially because a lot of that stash was bought using debt. Schiff’s point is simple: borrowing billions to hold a volatile asset works great when prices rise, but it gets ugly when they do not. You next buy will likely push your average cost above $70,000. The next leg down in Bitcoin will likely push the market price below your average cost. Not good considering how much you borrowed to buy the Bitcoin. When you sell, small paper losses will become huge real losses. — Peter Schiff (@PeterSchiff) May 12, 2025 The concern is not just Bitcoin itself - it is what happens if Strategy’s stock falls, too. The company trades under MSTR, currently at $413.44, with a $113 billion market cap and a $123.18 billion enterprise value. More than half of that value - 51.2% - is tied to Bitcoin. If the stock price drops, the collateral backing the company’s debt could weaken. That raises the possibility of forced sales, including BTC - something Saylor has avoided at all costs. Schiff’s criticism is not new, but it lands differently now. It id not just a philosophical disagreement - it is a math problem. Buying high, borrowing big and holding forever only works if Bitcoin keeps going up. If it does not, conviction turns into exposure, fast. Strategy has made it clear it does not plan to sell. But the more they buy, the more their cost basis rises - and the tighter the window gets. Schiff thinks that window is already closing.