bitcoin, says it sold 3,588 bitcoins (about $216m) over the course of a week. Until now, Saylor's strategy had never seen a reversal like this: since 2020, Strategy had only strengthened its bitcoin war chest, with the exception of 32 BTC sold in late May, building up more than 843,000 BTC. Remember, its long-standing motto had become legendary: "We buy, we hold, we never sell." That promise has now blown apart. Strategy shares are down -34% in 2026.

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Why the reversal?

The answer is first and foremost financial: Strategy said these large-scale sales are intended to fund dividends on its preferred shares and rebuild a USD cash reserve. Michael Saylor and his team unveiled in late June a "Digital Credit Capital Framework" that requires the company to maintain at least 12 months of liquidity to meet the bond payments tied to these high-yield securities.

Specifically, the company has several classes of preferred shares (STRC, STRK, STRF, STRD) that pay hefty dividends (STRC, for example, offers a 12% annual yield). In early July, those financial commitments hit a threshold where the company had to come up with fresh funds. Rather than drop into a USD financing spiral, Saylor chose the simplest route: liquidate part of the company's bitcoin treasury to generate cash.

This mechanism may surprise Bitcoin purists, but it follows straightforward arithmetic: sell a bit of bitcoin to fund those dividends. Preferred shares have seen their prices fall below their issue price (STRC dropped below $100, to as low as $71.25 in late June), given that their usefulness in financing new BTC purchases has collapsed. Faced with payment obligations, Strategy had little choice: shore up its cash position in a context where declines in certain lines are weakening its business model.

To put this in perspective, during the symbolic sale of 32 bitcoins ($2.5m) in late May 2026, the mere fact that the hearts of bitcoiners were racing was enough to push the market lower. This time, by selling more than 100 times that amount, Saylor is crossing a line.

After the transaction, MicroStrategy still holds 843,775 BTC, or more than 4% of the total bitcoin supply in circulation, purchased at a cost of about $63.7bn.

Strategy Treasuries

The large sale certainly crystallized a steep unrealized loss: at about $60,000 per unit sold, it sits well below the average purchase cost of about $75,476. In total, the unrealized accounting loss now stands at roughly $11.4bn. But that loss is largely theoretical as long as Saylor does not sell more. In the meantime, the operation preserved the USD reserve, now lifted to $2.55bn, allowing Strategy to meet its financial payments without permanently giving up its core assets.

A new strategic turning point

Michael Saylor himself used to hammer home that bitcoin was "digital energy" and that the goal was to accumulate ever more BTC. Today, he is tempering his message: he still posts accumulation charts on X, but now emphasizes institutional capital entering the ecosystem rather than the classic "halvings".

By formalizing a policy of selling bitcoin at Strategy, the company introduces the possibility of weighing on the price to the downside as much as to the upside.

For other companies that followed the same playbook (such as Bitcoin Treasuries, Metaplanet or other holding companies), Saylor's first historic sale is being watched closely. The question is whether they, too, could revisit their doctrine. Strategy's model rests on a triple lever: high-yield debt (preferred shares), the promise of dividends in bitcoin, and aggressive accumulation of BTC. When one of these pillars wobbles, the structure starts to crack. The sale highlights that fragility: faced with rising obligations, even the most hard-core hodlers have had to contend with financial reality.

Ultimately, the sale of 3,588 bitcoins is less a strategic repentance than a sign of operational maturity. The company showed it can execute the plan it set for itself to maintain solvency. Still, the pivot shakes the perception of a Saylor who would never touch his BTC. It raises questions about the long-term viability of an approach that finances risky purchases with structured borrowing.

For now, the market is absorbing the news without excessive panic. The weeks and months ahead will tell whether this reversal remains an isolated case tied to Strategy's unique situation, or whether it foreshadows an era in which even the biggest holders are willing to liquidate to secure their finances.