Michael Saylor spent years making the same promise. Never sell your Bitcoin. Not one satoshi. Strategy, the company he built around that conviction, held 843,775 Bitcoin through bull markets, bear markets, exchange collapses, and regulatory crackdowns, and never sold a single coin for four years straight.
In 2026, that streak ended. And it has not stopped ending.
CryptoQuant analysts estimate Strategy's cumulative realized losses from its 2026 Bitcoin sales have now topped $102 million.
These are not paper losses or accounting markdowns, they are actual cash losses from selling Bitcoin below the price the company paid for it.
Strategy sold Bitcoin five times in 2026. First, 32 BTC between May 26 and May 31 for $2.5 million at $77,135 per coin, the only sale executed above the company's cost basis at the time. Then 1,363 BTC for $80.8 million between June 29 and June 30.
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Then 2,225 BTC for $135.2 million between July 1 and July 5, the two combined representing 3,588 BTC for approximately $216 million at an average of $60,000 per coin, well below cost.
Then 1,638 BTC for $104.73 million between July 27 and August 2 at $63,957 per coin. Then 1,690 BTC for $108.6 million between August 3 and August 9 at $64,262 per coin.
Total Bitcoin sold in 2026: approximately 6,916 BTC for roughly $432 million. Every sale since the first has been executed below the company's average cost basis of $75,385 per coin. Current holdings stand at 840,447 BTC.
Here is the most surprising part of the story. Bitcoin spot ETFs have been averaging approximately $150 million in daily inflows, enough to absorb Strategy's selling without producing a measurable price impact.
Strategy has been selling into a market where institutional ETF demand has quietly absorbed every tranche without breaking the price.
That dynamic changes if ETF inflows slow.
Strategy's preferred stock dividend obligations have nearly quadrupled to $1.2 billion annually.
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The company's cash reserves dropped 38% in 2026 to roughly $1.1 billion by mid-June, before recovering to $4.65 billion through equity raises. The Bitcoin sales are not driven by a loss of conviction.
They are driven by a capital structure that now costs $1.2 billion a year to service regardless of what Bitcoin does.
CryptoQuant estimates Strategy is sitting on approximately $10.6 billion in aggregate unrealized losses, with every purchase made between 2024 and 2026 currently underwater.
The realized $102 million is the confirmed damage. The $10.6 billion is the potential damage if selling continues.
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This story was originally published by TheStreet on Aug 14, 2026, where it first appeared in the MARKETS section. Add TheStreet as a Preferred Source by clicking here.