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Strategy's Bitcoin Bet Turns Bitter as MSTR Drops Below $100 for First Time in Two Years

Bitcoin's 30% decline over the past 90 days — from roughly $87,000 to $60,770 — has broken the mechanism that made MicroStrategy's leverage play work.

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Strategy (MSTR) fell below $100 for the first time in two years on Wednesday, extending a drawdown that has erased roughly 81% from the stock's peak and approximately $153 billion in market value. The stock was down 9.26% on Wednesday to $94.13, with volume at 39 million shares — roughly 4x its average.

Bitcoin was trading at $60,770 Thursday morning, down 3.03% over the past 24 hours and 20.65% over the past month. The broader crypto selloff — ETH -2.90% to $1,617, SOL -2.82% to $67.56 — reflects a risk-off environment that has compounded pressure on equity proxies like MSTR.

The collapse maps directly onto Bitcoin's price deterioration. Strategy held 847,363 BTC as of June 21, worth roughly $53 billion at current prices. At BTC's September 2025 peak near $93,000, that same stack was worth approximately $78.8 billion — a $25 billion vaporization that has destroyed the equity cushion underpinning the company's leveraged swap structure.

That structure — swapping Strategy shares for Bitcoin via perpetual preferreds — only works when MSTR trades above the conversion price. Now the preferred (STRC) is trading near $84, well below its $100 par value, which strains the funding model.

CryptoQuant head of research Julio Moreno urged the company in a Tuesday report to pause BTC purchases and rebuild cash reserves. His analysis: annualized dividend obligations have climbed to roughly $1.2 billion, cutting dividend coverage from over seven years to about 14 months. Moreno estimated Strategy would need approximately $2.8 billion in reserves to restore 24 months of coverage — versus the $1.4 billion it currently holds.

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