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Strategy’s MSTR shares fell sharply on Wednesday, with the stock hitting its weakest level since March 2024 and dropping to an intraday low of $97.30. The move marked a nearly 5.5% decline for the session and renewed investor focus on the company’s cash position, preferred dividend obligations, and the potential implications for its Bitcoin holdings.
MSTR breached the $100 threshold on Wednesday for the first time since March 2024. After opening, the stock touched $97.30 and then traded around $98.05, reflecting a nearly 5.5% drop during the session. Over the prior five trading sessions, MSTR is down about 20%, and it is down more than 38% over the trailing month.
The decline coincided with weakness in Bitcoin. Bitcoin fell to about $60,935 on Wednesday, reaching a two-week low. The cryptocurrency has surrendered more than 50% from its peak above $126,000 reached in October.
Last week, Strategy offloaded approximately 2.71 million MSTR shares, raising roughly $335.5 million. Most of the proceeds were directed toward replenishing cash reserves rather than purchasing additional Bitcoin.
The company allocated $300 million to bolster its USD reserves, bringing total cash to $1.4 billion. Strategy’s executive chairman Michael Saylor said the cash accumulation strengthens the creditworthiness of Strategy’s Digital Credit instruments.
Only $35 million was used to acquire 520 BTC, a pace that differs from the company’s recent acquisition velocity, according to market participants.
Strategy’s preferred instrument, STRC, traded lower during the prior week, reaching a bottom of $82.53 and then around $84.35 on Wednesday, down 3.4% on the day. The company’s annual dividend commitments on preferred securities have risen to $1.2 billion, increasing scrutiny over how future payments may be funded.
Bitcoin skeptic Peter Schiff cautioned that aggressive short selling could push MSTR low enough to force Strategy’s leadership into selling Bitcoin to support stock buybacks. In a post on X dated June 24, 2026, Schiff said: “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,” but warned that “Bitcoin will crash” if Strategy is compelled to liquidate its cryptocurrency reserves.
Strategy carried out its first Bitcoin divestiture since 2022 earlier this month, ending its prior “accumulate and hold” approach. The transaction occurred as Bitcoin fell below $70,000, a timing that weighed on investor sentiment.
Year-to-date, MSTR’s valuation performance is down 31.66%. The company’s market capitalization is approximately $38.36 billion, and daily average trading volume is about 18.6 million shares. The technical sentiment indicator for MSTR currently shows a Sell signal.
The crypto bear market remained in force on Wednesday, with bitcoin slipping back toward the $60,000 area. Sharp pullbacks in gold and oil also weighed on the 2025 “debasement trade,” which had supported hard assets amid concerns about government debt and fiat currencies. Meanwhile, tech—particularly the AI boom—continued…
