TLDRMSTR plummeted to $97.30 on Wednesday, marking its weakest level since March 2024, declining approximately 5.5% during the sessionBitcoin slumped to roughly $60,935, hitting a two-week bottom, plunging more than 50% from its peak exceeding $126,000Strategy offloaded 2.71 million shares of MSTR last week, generating $335.5 million, with the majority allocated to cash holdings rather than Bitcoin purchasesYearly preferred dividend commitments have ballooned to $1.2 billion, sparking concerns Strategy might need to liquidate Bitcoin holdings to satisfy themPeter Schiff cautioned that aggressive short selling could compel Saylor to dump Bitcoin for stock buybacks, potentially triggering a Bitcoin price collapseLongtime Bitcoin skeptic Peter Schiff is keeping a vigilant eye on MSTR at this critical juncture — and he’s far from alone in his scrutiny.Strategy (MSTR) stock breached the $100 threshold on Wednesday, representing the first occurrence of such a decline since March 2024. The equity touched an intraday bottom of $97.30 moments after market open, subsequently hovering near $98.05, reflecting a nearly 5.5% decline for the session.Strategy Inc, MSTRThis positions MSTR down approximately 20% across the previous five trading sessions and exceeding 38% over the trailing month.The previous instance of MSTR changing hands below $100 occurred on March 1, 2024, coinciding with Bitcoin trading within the identical $61,000 to $62,000 corridor it currently occupies.Bitcoin itself declined to $60,935 Wednesday, establishing a two-week nadir. The flagship cryptocurrency reached an apex surpassing $126,000 this past October and has subsequently surrendered over 50% of that valuation.Bitcoin has faced mounting selling pressure as capital flows out of Bitcoin ETFs toward AI-focused equities. The Federal Reserve’s increasingly hawkish policy stance has compounded these challenges.Dilution Concerns Intensify Market AnxietyStrategy liquidated approximately 2.71 million MSTR shares during the previous week, generating roughly $335.5 million in proceeds. The vast majority was directed toward replenishing cash reserves instead of acquiring Bitcoin.The corporation allocated $300 million to bolster its USD reserves, elevating the aggregate to $1.4 billion. Executive Chairman Michael Saylor indicated the cash accumulation enhances the creditworthiness of Strategy’s Digital Credit instruments.Merely a modest fraction — $35 million — was deployed to acquire 520 BTC. This represents a significant departure from the company’s recent acquisition velocity and hasn’t escaped market participants’ attention.Strategy’s preferred instrument STRC, engineered to maintain proximity to $100, descended to a bottom of $82.53 during the prior week. It was exchanging around $84.35 Wednesday, declining 3.4% during the session. The organization’s annual dividend commitments on preferred securities have escalated to $1.2 billion, prompting speculation about funding mechanisms for future payments.Peter Schiff Issues Stark CautionPeter Schiff articulated his perspective on X, cautioning that aggressive short interest could depress MSTR sufficiently to corner Saylor strategically. “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 declared.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. That would reduce the discount, but it may not raise the share price, as Bitcoin will crash. That's the box Saylor put himself in.— Peter Schiff (@PeterSchiff) June 24, 2026He emphasized that executing such a maneuver “would reduce the discount” on MSTR equity but cautioned that “Bitcoin will crash” should Strategy be compelled to liquidate its cryptocurrency reserves.Strategy executed its initial Bitcoin divestiture since 2022 earlier this month, abandoning its longstanding “accumulate and hold” philosophy. That transaction undermined investor sentiment and aligned temporally with Bitcoin’s descent beneath $70,000.Strategy’s year-to-date valuation performance registers at -31.66%. Its market capitalization currently stands at roughly $38.36 billion. Daily average trading volume approximates 18.6 million shares.The technical sentiment indicator on MSTR presently registers as a Sell signal.The post Strategy (MSTR) Stock Plunges Under $100 as Bitcoin Slide Intensifies Pressure appeared first on Blockonomi.