Michael Saylor’s Strategy (MSTR) is showing a technical pattern last seen before the stock crashed 99% during the dot-com bust. The monthly chart is forming a head-and-shoulders setup, with the neckline sitting around $100–$105. A break below that could open the door to a measured target near $20 — roughly 80% down from current levels.
The pattern looks eerily similar to the one MSTR formed in the early 2000s before its historic collapse. But there’s more fuel for bears: Strategy’s cash reserve has dropped 38% since the start of 2026, while annual dividend obligations have nearly quadrupled to $1.2 billion.
That means the company now has enough cash to cover just 14 months of preferred stock dividends — down from over seven years of coverage. The preferred shares (STRC) have fallen to a record low of $82.50, well below their $100 par value, pushing the effective yield above 13%.
Strategy holds 847,363 BTC bought at an average of about $75,650 per coin. With Bitcoin trading around $62,600, selling would lock in losses. Instead, the company issued 2.71 million new common shares in June to raise $335.5 million, using only $34.9 million of that to buy 520 BTC — a move that dilutes existing shareholders.
If STRC stays below $100, expect more share issuance, slower Bitcoin purchases, or both. Each option puts additional pressure on MSTR as the stock tests a bearish breakdown.
