MicroStrategy shares cratered Wednesday, dropping as far as $92.28 before closing at $94.13, an 8% daily loss that completes a 20% slide over the past week and nearly 40% over the past month, according to Unchained Crypto. The move echoes Bitcoin's own tumble to a two-week low below $60,000.
The timing matters. Bitcoin has now fallen more than 50% from its October 2024 peak above $126,000. The Fed's more hawkish tone and sustained outflows from Bitcoin spot ETFs have compounded selling pressure through June. MicroStrategy, which holds 847,363 BTC at an average cost basis of roughly $75,653 per coin, is now underwater on its entire position—a particularly sharp turn for a company whose long-term thesis rests on Bitcoin appreciation.
But the sharper pain point is MicroStrategy's preferred share class, STRC, which reached a record low of $79.85 before recovering slightly to $80.84, down 6.5% on the day. STRC was designed to trade near $100. The security has funded billions of dollars in Bitcoin purchases this year, but market unease about the company's ability to service roughly $1.5 billion in annual dividend obligations without dipping into its Bitcoin holdings is now visible in the price.
That unease carries weight. Late last month, MicroStrategy sold 32 BTC to fund STRC dividends—a move that directly contradicts Chair Michael Saylor's long-standing "never sell your Bitcoin" posture. The company has since acquired more Bitcoin, but the market's verdict is clear: the choice to prioritize dividend payments over Bitcoin accumulation signals structural strain.
The core tension is now unavoidable. MicroStrategy structured STRC to let retail investors gain leveraged Bitcoin exposure without owning Bitcoin directly. As long as Bitcoin rises and MicroStrategy can service its obligations from cash flow, the setup works. But in a sustained downturn—especially one that pushes Bitcoin below the company's cost basis—the dividend commitment becomes a choice between burning cash or selling Bitcoin. Either path damages the thesis. Investors appear to be pricing in the likelihood that more sales are ahead.