Akshita Jhalani
Crypto Analyst
I want to take you through the exact sequence of events that turned Strategy's STRC preferred stock from a high‑yield, low‑volatility instrument into the most controversial product in crypto finance right now. Because the story isn't just about Bitcoin falling. It's about a chain of management decisions that each made sense in isolation, and then compounded into something that damaged investor confidence in a very visible way.
Where Things Stood on May 14
STRC closed at $100, its intended par value, heading into its monthly ex‑dividend date. Bitcoin was trading above $80,000. On the surface, everything looked fine.
But underneath, the picture was messier. Bitcoin had already fallen significantly from its October 2025 all‑time high of $126,000. STRC had only managed to hold $100 in the run‑up to the dividend date, not consistently throughout the month. And that same day, competitor Strive Asset Management announced it would pay dividends on its rival product SATA on a daily basis rather than monthly, directly pressuring Strategy's own shareholder vote to move STRC from monthly to semi‑monthly payments.
May 15: The Bond Buyback That Changed the Cash Math
The following day, Strategy announced it was repurchasing $1.5 billion of its 2029 convertible notes at an 8% discount. That sounds positive in isolation, retiring debt cheaply. But the buyback was partly funded using the dedicated cash reserve that Strategy had established specifically to cover dividend obligations and debt service.
That detail was not disclosed at the time. Bitcoin fell to $78,000.
May 26: The Reserve Problem Becomes Public
Strategy confirmed what it had done. The bond buyback had reduced the cash reserve from its original level to $871 million, roughly six months of STRC dividend coverage. The company had previously communicated a target of maintaining approximately 24 months of coverage. That gap between stated policy and actual position was immediately noticed.
STRC traded at $99.33. Bitcoin was around $77,000.
June 1: Saylor Sells Bitcoin for the First Time Since 2022
Strategy disclosed it had sold 32 BTC for approximately $2.5 million in late May to fund STRC dividend obligations. Thirty‑two coins out of 846,000. Numerically meaningless. Symbolically devastating. MSTR fell 5.9% that day. Bitcoin dropped as low as $70,500. STRC closed at $98.07.
The "never sell" identity that Saylor had built Strategy's brand around had its first public crack.
June 5: Bitcoin Falls Below $60,000
Bitcoin closed around $61,000, its lowest level since October 2024. STRC touched $90 intraday before closing at $93.40. The floor that investors had been quietly assuming existed was now visibly breaking.
June 8 to 15: Buying More Bitcoin While the Stock Bleeds
Strategy shareholders approved semi‑monthly STRC dividends. The company bought 1,550 BTC and then another 1,587 BTC the following week, replenishing its cash reserve to $1.1 billion. These were attempts to signal confidence. STRC kept declining anyway.
June 18: The Record Low
STRC fell below $83 intraday, 17% below its $100 par, before closing at $88.59 as U.S. markets headed into a holiday weekend. SATA fell alongside it.
Strive CEO Matt Cole attributed the move to leveraged liquidations rather than credit deterioration. That interpretation may be correct. But the underlying reality is harder to argue away.
Strategy now holds 846,842 BTC acquired at an average cost of $75,656 per coin. With Bitcoin near $62,500, that's an unrealized loss of roughly $11 billion. MSTR common stock trades around $112, down approximately 80% from its November 2024 all‑time high.
The capital structure built on top of Bitcoin works brilliantly when Bitcoin is rising. What the past five weeks demonstrated is exactly what happens when it isn't.