Strategy Sold Bitcoin for the First Time Since 2022 — Now Grayscale Thinks It Will Do It Again

TLDR

• Strategy’s 843,706 Bitcoin holdings have fallen into an $11.2 billion paper loss, with BTC trading well below the company’s average purchase price of $75,699.
• Michael Saylor called the downturn a “capital rotation, not a Bitcoin impairment,” pointing to ETF outflows and AI infrastructure spending.
• Strategy’s preferred stock STRC has dropped below its $100 par value to around $94–95, raising concerns about future dividend obligations.
• Grayscale Research warned Strategy will likely need to sell more Bitcoin to meet cash flow needs, with its ability to buy more BTC limited at current stock prices.
• Standard Chartered sees a potential market bottom forming and maintained its $100,000 year-end Bitcoin price target, with the bank watching Strategy’s next purchase for confirmation.

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Bitcoin’s slide below $64,000 has pushed Strategy, the largest corporate Bitcoin holder in the world, into an $11.2 billion unrealized loss on its holdings.

The company holds 843,706 Bitcoin, bought at an average price of $75,699 per coin. That gives Strategy a total cost basis of $63.8 billion. With Bitcoin trading around $63,000 to $64,000 at the time of reporting, the current value of those holdings sits at roughly $52.6 billion.

Bitcoin is down about 4.7% in the last 24 hours, 13.8% over the past week, and more than 20% in the past month.

Saylor Pushes Back on Bearish Outlook

Strategy co-founder Michael Saylor posted on X saying the pressure on Bitcoin is coming from ETF outflows and a surge in capital going into AI infrastructure. Spot Bitcoin ETFs have seen $4.4 billion in outflows over the last 13 trading days.

Saylor described the situation as a “capital rotation, not a Bitcoin impairment,” adding that “volatility creates opportunity.”

Capital markets are funding the AI buildout at historic scale: ~$400B over 6 months. Bitcoin ETFs have seen ~$4B of outflows since May 14, pressuring $BTC. This is a capital rotation, not a Bitcoin impairment. Volatility creates opportunity.

— Michael Saylor (@saylor) June 4, 2026

His comments came days after Strategy sold 32 Bitcoin — its first Bitcoin sale since 2022. That sale drew fresh attention to the company’s leveraged business model and its ability to keep buying Bitcoin.

STRC Drop Raises Cash Flow Concerns

Strategy’s variable-rate preferred stock, STRC, has fallen to around $94–95, below its intended $100 par value.

The stock was designed to trade near $100 with an 11.5% dividend. When it drops below that level, the company is pressured to raise its dividend to attract buyers back. That means higher cash flow obligations for the company.

Grayscale Research head Zach Pandl said Strategy will likely need to sell more Bitcoin in the future to meet those obligations. He also said Strategy’s ability to buy more Bitcoin is limited at current prices for both MSTR stock and STRC.

Strategy’s main stock, MSTR, was down around 1.5% in pre-market trading at $124.70 at the time of reporting.

Some analysts, including investor Scott Melker, downplayed the STRC drop, saying a 5% discount to par is normal behavior for preferred stock in uncertain markets.

Gold investor Peter Schiff took the opposite view. He argued that a continued fall in STRC would force Strategy to increase dividend payments and eventually accelerate Bitcoin sales to cover those costs.

What Analysts Are Watching

Grayscale noted that while this near-term pressure may weigh on Bitcoin, it could be a positive long-term shift. Moving Bitcoin off leveraged corporate balance sheets and into more diversified corporate treasuries may support a stronger recovery.

Standard Chartered maintained its year-end Bitcoin price target of $100,000. The bank said a potential market bottom may be forming, and that a new Bitcoin purchase by Strategy — whether 320 BTC or 3,200 BTC — could confirm that the low is in.

After Strategy’s tax-loss sale of 704 Bitcoin in 2022, the company bought 810 Bitcoin just two days later.