The sale extinguished a convertible note — the "Smarter Convert" — that could have produced 7.72 million new shares, allowing the company to avoid equity dilution entirely . The company's CEO noted that the convertible structure was "no longer optimal" given the lower share price, and the sale aligned with its capital protection strategy
.
Crucially, The Smarter Web Company was not exiting its Bitcoin position. After the sale, it still held approximately 2,700 BTC, making it the 28th largest public corporate Bitcoin holder at the time . (Before the sale, the company had reported holdings of 2,878 BTC
.) By selling essentially all the Bitcoin it had purchased the prior year, the company reduced its cost basis exposure
.
Strategy, the world's largest corporate Bitcoin holder, conducted two distinct sell-offs in mid-2026 totaling approximately 3,620 BTC. The sales marked an epochal shift: Michael Saylor's company abandoned its long-held "never sell" mantra .
Strategy sold a small portion of its Bitcoin holdings in late May / early June 2026 — its first Bitcoin sale since 2022 . This initial liquidation, though tiny by Strategy's standards, triggered a sharp market downturn. Bitcoin dropped under $70,000 for the first time since April 2026, and subsequently cracked $60,000 by June 5, 2026
. CNBC noted the sale was small but marked a psychological break from Saylor's "never sell" philosophy
.
Between June 29 and July 5, 2026, Strategy sold 3,588 BTC for approximately $216 million — the largest single Bitcoin liquidation in the company's history . The sale was executed in two tranches:
The proceeds were used to fund dividends on preferred security holders and replenish U.S. dollar reserves . At the time, Strategy still held 843,775 BTC and had a USD reserve of $2.55 billion
.
In its Q2 8-K filing on July 6, 2026, Strategy reported an $8.32 billion loss on digital assets for the second quarter. The Wall Street Journal confirmed this figure, noting the majority was unrealized . Detailed breakdowns showed $8.31 billion in unrealized losses (mark-to-market) and only $0.9 million in realized losses
. The impairment reflected Bitcoin trading below Strategy's average acquisition cost of approximately $75,476 per coin
.
Bitcoin peaked at approximately $126,000 in October 2025 . By mid-2026, it had fallen roughly 50% from that peak, trading near $58,000–$61,000 by late June 2026
. The $62 billion in corporate treasury value that evaporated was a stark measure of the damage
.
According to VanEck Head of Digital Assets Research Matthew Sigel, several companies exited crypto entirely, and many more were reducing holdings substantially . CoinDesk reported on July 24, 2026, that Bitcoin treasury companies were "unwinding holdings as the DAT model comes under pressure," with share prices collapsing and firms pivoting to AI or other businesses
. Multiple sources confirmed that the sell-off wave included nine companies fully exiting their Bitcoin treasuries
.
Strategy abandoned its long-held "never sell" stance, first with the small May sale and then decisively with the July 3,588 BTC liquidation . The company adopted a new treasury management framework authorizing up to $1.25 billion in coin sales, marking a formal departure from pure accumulation toward active debt and liquidity management
. The New York Post called it "a departure from co-founder Michael Saylor's principle of 'never sell your Bitcoin'"
.
Several Bitcoin treasury companies faced acute cash-flow pressure as their Bitcoin collateral values declined, convertible debt covenants tightened, and share prices collapsed . The Smarter Web Company's early debt repayment was explicitly framed as a liquidity-preserving move
.