Strategy’s First Bitcoin Sale in Years Fuels Dividend Acceleration as Stock Trades at Deep Discount

The gap between Strategy’s operational reality and its stock price has never been wider. Shares of the Bitcoin treasury company have shed nearly 30% over the past month, closing Friday at €107.14 – a level that represents an 18% discount to the net asset value of the company’s Bitcoin holdings. Investors are effectively buying the crypto asset at a markdown through the equity, yet the market remains sceptical.

Behind the scenes, management is deploying a two-pronged approach to address both short-term shareholder returns and long-term positions. In a move that broke a four-year taboo, Strategy sold 32 Bitcoin for roughly $2.5 million at the end of May – its first disposal of the digital asset since 2022. The sale was immediately followed by the purchase of 1,550 Bitcoin for approximately $101 million, lifting the corporate hoard to over 845,000 coins by early June.

Chief Executive Phong Le outlined three reasons for the rare sell-off: crystallising tax losses, stress-testing the company’s trading systems, and pre-positioning the market for potential future disposals. Executive Chairman Michael Saylor, long an apostle of “hodl”, defended the decision, stressing the need for financial flexibility even as his personal philosophy remains unchanged. The proceeds will be used to fund dividend payments on the company’s preferred stock.

Shareholders at the annual general meeting on June 8th approved a change to the payout rhythm of the Series A preferred shares. From now on, dividends will be distributed twice a month rather than monthly. The new schedule kicks in at the end of June, with record dates set for the 15th and the last day of each month. The first payout under the new tempo is slated for July 15, 2026.

Should investors sell immediately? Or is it worth buying Strategy?

The broader crypto backdrop, however, is working against Strategy. The massive initial public offering of SpaceX in the second quarter of 2026 has sucked up billions of dollars in private capital, starving alternative assets like Bitcoin of liquidity. US spot Bitcoin ETFs have suffered $2.1 billion in outflows since the start of June, and the Bitcoin price briefly slipped below $60,000. Analysts at JPMorgan see the narrative of Bitcoin as an inflation hedge fading.

Insider activity has also caught the market’s eye. Chief Financial Officer Andrew Kang sold a block of shares worth around $241,000 on June 9, shortly after receiving equity from a compensation programme. He continues to hold a substantial personal stake.

Analysts remain cautiously constructive despite the headwinds. Mizuho and Canaccord recently slashed their price targets but maintained buy ratings, betting on a return to profitability. On a technical basis, the relative strength index stands near 38, flashing an almost oversold condition. Cash-flow-based models peg fair value at roughly $156 (approximately €145), implying considerable upside from current levels. Yet the stock remains firmly below its 200-day moving average of around €163, and only a clean break above that resistance would materially brighten the chart picture.