Saylor's Treadmill Hits a Wall: MSTR Stumbles Under $100, Schiff Smells 🩸

Strategy (MSTR), the largest publicly traded corporate holder of Bitcoin, saw its common shares drop below $100 on Wednesday for the first time since March 1, 2024, slipping to an intraday low of $97.30 roughly 30 minutes after the opening bell and recently trading at $98.05, a decline of about 5.5% on the day, according to Yahoo Finance. The slide extends a sharp pullback, with MSTR down roughly 20% over the past week and more than 38% over the past month, even as the company continues to raise cash by issuing equity to fund additional Bitcoin purchases. Strategy last disclosed adding $300 million to its so-called USD reserve through common stock issuance, lifting that reserve to $1.4 billion and generating $335 million in proceeds, according to a company press release.

Bitcoin itself fell alongside the stock, with $BTC dropping to $60,935, its lowest level in two weeks and down more than 50% from its all-time high above $126,000 set in October. The decline comes as investors have pulled money from Bitcoin ETFs and as the Federal Reserve has adopted a more hawkish tone, with capital rotating toward artificial intelligence equities. MSTR shares had peaked above $400 in 2025 as Bitcoin rallied following President Donald Trump's more crypto-friendly policies and the optimism those policies generated among digital asset traders.

The sell-off in Strategy's equity has spilled into its preferred-share structure. The STRC preferred, which is designed to trade near $100, fell to a low of $82.53 last week and was recently changing hands at $84.35, down 3.4% on the day, amid growing concerns that the firm may be forced to sell Bitcoin to meet dividend obligations on the instrument. Those fears echo Bitcoin's drop below $70,000 in early June, which coincided with Strategy's first Bitcoin sale since 2022, a transaction that broke the long-standing "buy and never sell" stance repeatedly articulated by co-founder and executive chairman Michael Saylor.

Gold advocate and long-time Bitcoin critic Peter Schiff weighed in on the action, writing on X that "If short sellers push $MSTR's price low enough, they can put Saylor in a position where his best option would be to sell Bitcoin to buy back stock." Schiff added that such a move "would reduce the discount" on MSTR shares but cautioned that "Bitcoin will crash" if the company is compelled to liquidate holdings. Strategy is headquartered in Tysons Corner, Virginia, and pioneered the corporate crypto-treasury model that has since spread to other digital assets.