$3,868,168,653: Saylor’s Strategy Loses on Recent Bitcoin Purchases

The biggest corporate buyer of Bitcoin, Strategy (formerly MicroStrategy), is under tremendous pressure as a result of the recent decline, as the company now faces an amazing $3.86 billion in unrealized losses in its recent Bitcoin acquisitions. Michael Saylor led the company’s aggressive accumulation strategy, which has drawn praise and criticism. It has a major impact on the price fluctuations of Bitcoin.

The approach is being tried more than ever before, though, as Bitcoin by fell more than 13% in 2025. Since the beginning of 2025, Strategy has purchased Bitcoin for about $5.3 billion, but the price of the cryptocurrency has only decreased. A famous Bitcoin critic, Peter Schiff, recently drew attention to this issue, pointing out that Bitcoin’s decline might have been even more severe if Saylor did not make these purchases. Schiff raised another question: What would happen if Saylor began to sell?

Bitcoin has now dropped significantly below the $95,000 to $105,000 price range at which Strategy’s recent purchases were made. The company’s enormous Bitcoin holdings could become a liability if the trend continues, requiring tough financial choices. The market is becoming complacent, with many investors believing that Bitcoin will rebound just because it has in the past.

Technical indicators and macroeconomic conditions, however, indicate that a further decline to the $50,000-$60,000 range is not implausible. This would place MSTR’s Bitcoin holdings below their average cost basis.

Strategy is still steadfast in its Bitcoin strategy for the time being, but if the market keeps falling, it will be difficult to tell if it will hold firm or if it will have to change course — which could cause even more volatility on an already unstable market.

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