The Saylor Pivot: Strategy Breaks "Never Sell" Vow to Fuel Dividends

Strategy (formerly MicroStrategy) said on May 5, 2026, that it is ready to sell parts of its Bitcoin holdings, a shocking break from its long-running "never sell" attitude. CEO Michael Saylor presented the policy change as a strategic move to pay dividends for the company's STRC preferred shares, rather than as a sign of financial trouble. The company hopes to normalize the concept of Bitcoin-funded payouts while stressing that its underlying belief in the digital asset hasn't changed by labeling the move a one-time "inoculation" of the market.

The financial rationale of the decision is based on meeting the USD 1.5 billion in yearly dividend expenses. To maximize tax efficiency and improve the balance sheet, particularly when selling assets turns out to be more accretive than issuing new equity, management aims to use high-cost-basis Bitcoin for these sales. Despite the appearance of the turn, the scope of the liquidation is rather small; with a large treasury worth more than USD 66.4 billion, the monthly sales would constitute just 0.18% of the total stack, offering enough coverage to support the policy for over 44 years.

Investors were first skeptical, as Strategy's stock dropped over 4% after the Q1 earnings call, as the market changed to the new reality. But the company is still aiming for rapid growth, to become the biggest business in the world by seeing the value of "Bitcoin per share" rise. The company expects a net growth of 144,000 BTC over the next three years, even with dividend-related liquidations, based on a projected 17.7% yield and ongoing high-volume purchases to balance out the outflows.