According to reports from Investing.com, Strategy has sold Bitcoin for the first time in years, marking a significant shift in the company's approach to cryptocurrency holdings. The company sold 32 BTC between 26 May and 31 May for approximately $2.5 million, with proceeds expected to help fund preferred stock distributions. This represents the first Bitcoin sale since December 2022, when Strategy sold 704 BTC for tax-loss harvesting and subsequently bought back 810 BTC just a few days later. The sale was executed at an average price of $77,135 per coin, as reported in Monday's regulatory filing, marking only the second time the company has ever liquidated any of its flagship holdings. The move has drawn significant attention from investors and market observers, particularly given the symbolic weight of breaking from Michael Saylor's defining 'never sell' doctrine. Bitcoin slid to $71,192.7 by 17:22 ET, hitting an over seven-week low after the announcement, with the world's largest cryptocurrency down 3.6% on the news. The disclosure triggered immediate market reactions, with more than $93 million in crypto futures positions liquidated in a single hour, with 95% of those being long positions.
The Bitcoin sale had immediate market implications, with Strategy shares dropping more than 6% in premarket trading following the announcement. Bitcoin itself fell 2% on the news, dropping to its lowest level since April 13. In the same filing period, Strategy also sold 801,994 shares of common stock, raising $128.3 million according to the regulatory filing. This represents the first Bitcoin sale since December 2022, when Strategy sold 704 BTC for tax-loss harvesting and subsequently bought back 810 BTC just a few days later. Despite the small size of the recent sale, the move has raised questions about Strategy's long-standing 'never sell' Bitcoin position. The broader crypto market also declined, with world no.2 crypto Ether shedding 0.8% to $1,996.43, while XRP slipped 3% to $1.2934, and Solana and Cardano were down 1.9% and 2.2% respectively. MSTR shares fell 5.15% in premarket trading following the announcement, with the stock closing down 9.95% on the day and having shed nearly 70% over the past year.
The sale follows a formal strategic shift the company announced earlier this year, stepping away from the 'never sell' posture long associated with Saylor in favor of actively managing its balance sheet. Under the new framework, Strategy may sell bitcoin if doing so improves bitcoin-per-share metrics, funds dividends, or otherwise strengthens the company's financial position. CEO Phong Le explained on the company's earnings call in early May that "We want to be net aggregators of bitcoin — increasing our total bitcoin, but more importantly, increasing our bitcoin per share because we think that is what is going to be most accretive long term for MSTR." Central to the revised approach is STRC, a yield-paying security issued by Strategy that lets investors earn income backed by the company's bitcoin-heavy balance sheet rather than purchasing bitcoin directly. The instrument is designed to function as a credit engine, with investor demand for income products theoretically enabling the company to grow its bitcoin holdings faster than a simple buy-and-hold model would allow. As of May 31, Strategy holds 843,706 BTC worth approximately $61 billion at current prices, with a total cost basis of $63.87 billion, representing more than 4% of bitcoin's fixed 21 million coin supply. The recent sale represents only 0.0038% of the total position, but the optics have raised concerns about the company's ability to maintain its aggressive bitcoin accumulation strategy.
The Bitcoin sale comes amid significant institutional selling pressure, with ETFs linked to the world's largest cryptocurrency seeing a $1.4 billion outflow from U.S. ETFs in the past week, according to data from aggregator SoSoValue. This represents the third straight week of over $1 billion capital outflows from Bitcoin ETFs, with last week's outflow also coming from a $1.26 billion block sale of BlackRock's IBIT, which crypto investment firm NYDIG said was likely a rapid exit by a large investor. U.S. spot ETFs logged 10 consecutive sessions of outflows between May 15 and May 29, draining $2.97 billion — a new record breaking the previous eight-session streak from early 2025. May is tracking as the third-worst month since launch at approximately $2.4 billion in net outflows, behind only February and November 2025. As per Nexo Dispatch analyst Dessislava Ianeva, "The risk is that this unwind has further to run. As per Glassnode data, Q2 spot CVD has been negative in four of the past five years and Q3 weaker still, and with summer liquidity thinning, a U.S.-Iran resolution may prove the more consequential variable than any technical level." Research from TD Cowen supports the notion that MicroStrategy's Bitcoin purchases account for only about 3.3% of weekly trading volume and show little correlation with Bitcoin's price movements, suggesting the company's transactions are overshadowed by broader market forces.
Bitcoin's technical indicators suggest continued bearish momentum despite the recent sale. BTC is trading below $72,000 at press time on Monday, maintaining a bearish near-term tone as it holds below the 50-day and 100-day Exponential Moving Averages clustered around $76,052 and $76,505, while the 200-day EMA near $81,086 remains well overhead as a broader cap. Momentum remains fragile, with the Relative Strength Index (RSI) at 31 on the daily chart, hovering just above oversold territory, while the Moving Average Convergence Divergence (MACD) indicator is entrenched in negative territory. On the downside, immediate support aligns with the rising trendline around $71,329, which now acts as a nearby floor to monitor for a deeper slide. Any rebound faces initial resistance at the 50-day EMA near $76,052, followed by the 100-day EMA around $76,506, while a more decisive recovery would require a break above the 200-day EMA at approximately $81,087 to ease the broader bearish bias. Bitcoin slumped 8.58% to trade near $67,206, extending a slide below $70,000 tied to record ETF outflows, with the cryptocurrency erasing approximately $160 billion in total crypto market value within the week following the sale announcement.
