Saylor reaffirms Bitcoin bet as Strategy stock sinks to $86

Strategy's stock fell 8% to $86 on June 25, its lowest since February 2024, as the company's Bitcoin funding model showed signs of strain.

"Volatility tests capital structure," Michael Saylor, executive chairman of Strategy, wrote on X on June 26, reaffirming the company's commitment to Bitcoin. Alexander Blume, chief executive officer at Two Prime, said Saylor's "repeated pivots and deviations from his stated plans" have broken investor trust, particularly among retail buyers who were sold STRC as a retirement income product.

Strategy holds about 847,000 Bitcoin worth roughly $51 billion at current prices, while the company's market capitalization stands at about $31 billion. The premium that once reached 3.4 times the value of its Bitcoin holdings has essentially disappeared, with the mNAV multiple compressing to 1.05. The company's perpetual preferred stock, STRC, has fallen to $75, a 25% discount to its $100 par value, effectively shutting off the funding loop that powered most of Strategy's Bitcoin purchases in 2026. The company faces a $1.7 billion annual cash dividend bill on its preferred shares, with about $1.4 billion in cash reserves — roughly 10 months of coverage.

The breakdown of Strategy's funding model removes the most consistent institutional buyer from the Bitcoin market at a time when spot Bitcoin ETFs are bleeding capital. Bitcoin briefly touched a 21-month low of $58,131 on June 25, extending its decline from the October 2025 peak above $126,000. For Strategy to resume buying on favorable terms, the stock needs to climb back above roughly $183, which requires Bitcoin to push toward $91,500.

Strategy sold 32 Bitcoin in late May for about $2.5 million, its first sale since 2022, with the company stating in an SEC filing that it expected to use proceeds from Bitcoin sales to fund preferred share dividends. The amount represented about 0.004% of its holdings, but the shift in posture marked a departure from Saylor's long-standing pledge that Strategy would never sell.

Crypto analytics firm CryptoQuant recommended in a June 25 report that Strategy halt Bitcoin purchases and rebuild cash reserves, arguing the company's strategy of buying during price dips has resulted in rapid unrealized loss growth. JPMorgan analysts issued a similar warning earlier in June, concluding that Strategy's dollar reserves should be rebuilt to restore confidence.

A stress test conducted by analyst Adam Livingston, who is bullish on Strategy, modeled a scenario in which Bitcoin crashes to $26,600, capital markets close and the company is forced to sell coins to cover obligations. Even in that worst case, Strategy would survive with more than 731,000 Bitcoin remaining after three years, though the Bitcoin backing per share would fall by about 94%.

Strategy's debt is mostly long-dated, with the earliest lender put option arriving in late 2027. The immediate pressure is the cash dividend, not a looming debt maturity. For the funding loop to restart, MSTR must climb back above roughly $183, a level that aligns with Bitcoin near $91,500.

This article is for informational purposes only and does not constitute investment advice.