Story perspectives

Michael Saylor's Strategy Faces Bitcoin Dilemma Amid Debt Crisis

2/20/2026

Summary

Story summary

Strategy, led by Michael Saylor, issued new shares to preserve Bitcoin holdings amid falling prices.
Since 2020, shares rose from 76 million to 314 million, a 313% increase.
Strategy's Bitcoin per share metric rose initially, then faltered as shares fell 72% from peak.
Strategy's debt reached $8.2 billion, with high dividends on preferred stock straining finances.
Saylor plans to refinance by issuing more shares, risking dilution and undermining the Bitcoin-per-share goal.

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Story summary

Strategy, led by Michael Saylor, issued new shares to preserve Bitcoin holdings amid falling prices.
Since 2020, shares rose from 76 million to 314 million, a 313% increase.
Strategy's Bitcoin per share metric rose initially, then faltered as shares fell 72% from peak.
Strategy's debt reached $8.2 billion, with high dividends on preferred stock straining finances.
Saylor plans to refinance by issuing more shares, risking dilution and undermining the Bitcoin-per-share goal.