Strategy shows no fear — it keeps adding to a losing bitcoin position as prices drop

MarketWatch

by Tomi Kilgore

February 23, 2026

AI-Generated Deep Dive Summary

**Strategy MSTR Continues Aggressive Bitcoin Purchases Despite $8 Billion Loss** In a move that has raised eyebrows in financial circles, Strategy MSTR, the largest corporate holder of Bitcoin (BTCUSD), has disclosed additional purchases of $40 million worth of the cryptocurrency. This decision comes despite its total bitcoin holdings now being valued at nearly $8 billion below market value, as prices continue to drop and the company's position deepens into the red. The announcement sent shares of Strategy MSTR dropping on Monday, reflecting investor concerns about the risks involved in holding such a large and losing Bitcoin portfolio. The company's strategy appears to be doubling down on its belief in Bitcoin's long-term potential, even as short-term market conditions remain challenging. By selling common shares to fund these purchases, Strategy is signaling a willingness to invest significant capital into bitcoin despite ongoing losses. This approach has drawn mixed reactions from analysts and investors, with some applauding the company's boldness and others questioning whether such a risky strategy could lead to further financial strain. For readers interested in finance and markets, this situation highlights the volatility and risks associated with cryptocurrency investments on a large scale. Strategy MSTR's actions also serve as a case study in corporate risk tolerance and decision-making in the face of significant losses. The company's continued commitment to Bitcoin underscores its confidence in the asset's future, even as it struggles to navigate a bearish market environment. Ultimately, whether this strategy proves successful will depend on how Bitcoin's price develops moving forward. For now, Strategy MSTR remains at the center of a broader conversation about the potential rewards and pitfalls of holding substantial amounts of cryptocurrency during periods of market decline.

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Originally published on MarketWatch on 2/23/2026