Finbold
April 6, 2026 12:42 PM UTC

Michael Saylor’s Strategy sits on the biggest unrealised losses in history

Michael Saylor’s Strategy (NASDAQ: MSTR ), a business intelligence company formerly known as MicroStrategy, is now sitting on record $10.8 billion in unrealized losses. After six years of its characteristically aggressive and bullish Bitcoin ( BTC ) acquisitions, the company is now down 17% on its flagship crypto position, according to the latest data published by The Kobeissi Letter . More specifically, Strategy had invested a total of $63.89 billion in Bitcoin, while its current balance hovers around $53.08 billion, as the asset itself has dropped below $62,500 – the biggest unrealised losses in history, as per the same data. At the same time, MSTR shares are down 77% since their record high, while the S&P 500 has gained no less than 116% since Saylor began investing in BTC. Strategy’s unrealised losses. Source: The Kobeissi Letter Strategy currently holds 843,706 BTC, which is 4.02% of the total BTC Supply. Saylor’s Strategy faces financial pressure Strategy faces further financial pressure as it currently holds approximately $6.7 billion in notional debt, as per the company’s official website, with substantial annual dividend and interest payments pending. Moreover, Strategy’s cash position had fallen to roughly $871 million by the end of May, following $1.5 billion in convertible debt repurchases. For context, the figure is only enough to cover around six months of the company’s estimated $1.7 billion annual preferred dividend obligations. This is especially notable as the company has also proposed increasing the dividend payment frequency for its STRC preferred shares from monthly to twice monthly. For now, investors are waiting for the June 8 shareholder meeting to see whether the idea will be realized or not. Meanwhile, concerns surrounding Bitcoin’s ongoing weakness and deteriorating investor sentiment are not only weighing on the company’s shares but also raising concerns about its underlying business principles . However, some market analysts, including known crypto bears such as Peter Schiff, are now arguing that Bitcoin might have found support around $61,000 , levels comparable to February lows that preceded a notable rally once traders had absorbed stock market corrections. Featured image via Shutterstock The post Michael Saylor’s Strategy sits on the biggest unrealised losses in history appeared first on Finbold .