Strategy avoids crisis-level stress signals even as hedging surges, Anchorage says
Strategy’s options are not flashing the kind of alarm that typically accompanies a company-specific crisis, despite a sharp pickup in defensive positioning across the broader Bitcoin complex, according to new analysis by Anchorage Digital.
In a June 25 report, David Lawant, head of research at Anchorage Digital, wrote that traders in Bitcoin options, BlackRock’s iShares Bitcoin Trust (IBIT), and Strategy’s stock (MSTR) are paying elevated premiums for downside protection. Yet, he concluded that the options market tied specifically to Strategy remains short of the extreme stress levels historically associated with expectations of forced deleveraging or imminent corporate distress.
Anchorage’s study compared options activity across Deribit’s Bitcoin contracts, IBIT options, and MSTR options, arguing that this three-part view offers a more rounded snapshot of risk sentiment. Deribit reflects crypto-native traders, IBIT captures institutional flows, and MSTR options bridge crypto and traditional equity investors. Taken together, they show a market bracing for more turbulence, but not yet pricing a meltdown at Strategy itself.
Put skew – the relative expensiveness of put options versus calls – remains notably elevated in both Deribit and IBIT markets. That pattern indicates investors have been more interested in insulating portfolios from losses than in paying up for additional upside. According to the report, defensive positioning currently sits in the 82nd percentile of IBIT’s historical readings and the 84th percentile of Deribit’s last five years, underscoring how cautious traders have become.
Lawant also highlighted an unusually persistent volatility structure in Bitcoin options during 2026. Nearly half of the year so far has seen one-week implied volatility trade above one-month implied volatility, an inversion that typically signals intense concern about near-term catalysts. Anchorage attributed this to a constant drip of macroeconomic data releases, geopolitical flashpoints, and crypto-specific developments that keep traders focused on the next few days rather than the next few months.
A reversion to the more conventional pattern – where one-month implied volatility trades above one-week volatility – would suggest that investors are once again comfortable taking a longer view and are less fixated on immediate shocks. For now, however, the short end of the curve is where traders are paying the highest premium for protection, implying expectations of choppy trading ahead.
Within that broader backdrop of heightened caution, Strategy’s derivatives still look relatively orderly. Anchorage’s research notes that while there is steady demand for MSTR put options, the level of put skew has not spiked into the zone that typically accompanies fears of a company-specific liquidity crunch, margin spiral, or broader solvency scare. In other words, the market is clearly nervous, but not yet panicked about Strategy’s survival.
This more measured options pricing contrasts with the visible strain in Strategy’s capital structure. The company’s perpetual preferred stock, STRC, slid to $82.53 on June 22 – roughly 17% below its $100 par value – before briefly rebounding after the company disclosed that it had increased its fiat reserves to $1.3 billion. Even so, by Thursday STRC was trading near $75, leaving it about 25% below par and signaling that investors continue to demand a steep discount to hold the preferred shares.
The pressure has spilled over into Strategy’s common equity as well. Data from financial market trackers show MSTR trading around $85 on Thursday, down approximately 78% over the past year and marking a new 52-week low. The collapse in the share price underscores how sharply sentiment has turned against the company, whose stock once served as a high-beta proxy for Bitcoin upside.
Beyond the trading screens, Strategy is facing mounting legal and governance questions. Rosen Law Firm has announced an investigation into whether the company issued materially misleading business disclosures. The firm is assessing possible securities law violations and exploring the potential for a class-action lawsuit on behalf of shareholders that have suffered losses.
The scrutiny intensified after vocal Bitcoin critic Peter Schiff argued that investors in Strategy’s STRC preferred stock might have legal standing to pursue claims if they bought based on public promotion of the company’s Bitcoin treasury strategy by Executive Chairman Michael Saylor. Schiff made those comments before any law firm had formally disclosed an investigation into potential shareholder claims, but his remarks added fuel to worries around legal exposure and investor protections.
Investor anxiety was further stoked by insider selling. Strategy director Jarrod Patten recently sold an additional 1,500 MSTR shares as the stock continued to slide, a move that can be interpreted as either routine portfolio management or a signal of diminished confidence. In a market already primed for bad news, such sales tend to be read through a pessimistic lens.
Despite these accumulating negatives – a collapsing share price, a discounted preferred stock, and intensifying legal scrutiny – Anchorage Digital’s options analysis suggests that traders are primarily bracing for volatility, not for a full-blown corporate breakdown. Pricing still reflects the expectation of sizable swings in Strategy’s equity, but not the kind of disorderly move that would typically accompany fears of forced asset sales or an imminent restructuring.
Strategy’s role in the crypto ecosystem remains central. Under Michael Saylor’s leadership, the company pioneered the corporate Bitcoin treasury model in 2020 and has since become the largest public-company holder of Bitcoin, with 847,363 BTC on its balance sheet. That concentration means any perceived weakness in Strategy is quickly interpreted as a proxy for broader sentiment toward the Bitcoin-as-treasury-reserve thesis.
This structural position helps explain why the market’s reaction is so nuanced. On one hand, investors are clearly uncomfortable: they are heavily hedged, pushing downside protection to historically high percentiles, marking down both the common and preferred equity, and paying close attention to legal developments. On the other hand, options pricing stops short of indicating a systemic unraveling at Strategy, which suggests that traders still see a path through the turbulence.
For equity holders, the current options landscape carries several implications. Elevated put skew on MSTR means that protection is expensive but available; investors can still hedge downside risk, but they must pay a sizable premium to do so. At the same time, the absence of an outright “crisis premium” in Strategy’s options implies that the market has not yet fully embraced the worst-case scenarios being debated by critics.
For holders of STRC, the steep discount to par reflects a more cautious calculus. Preferred investors rank above common shareholders in the capital structure, yet the price at $75 indicates doubts about the durability of distributions and the perceived risk embedded in Strategy’s highly leveraged Bitcoin strategy. The company’s move to bolster fiat reserves to $1.3 billion has provided some reassurance, but not enough to close the gap to par.
From a broader market perspective, the divergence between spot prices, credit-like instruments such as STRC, and options-implied risk premiums on MSTR and Bitcoin offers a detailed look at how different investor classes are reacting. Crypto-native traders on Deribit appear most focused on short-term volatility, institutions using IBIT are heavily hedged but still engaged, and equity and preferred investors in Strategy are applying a more skeptical lens to the company’s balance sheet and legal outlook.
If volatility expectations eventually normalize – with one-month implied volatility rising back above one-week levels – and put skew in Bitcoin and IBIT recedes from its elevated percentiles, that could signal that the worst of the fear-driven hedging cycle is over. In such a scenario, focus would likely shift from immediate survival questions to medium-term fundamentals: Strategy’s leverage, its BTC acquisition pace, regulatory developments, and the company’s ability to manage through drawdowns without diluting shareholders further.
Conversely, if legal actions escalate or Strategy’s financial position weakens further, the options market would be expected to reflect that quickly. A sharp spike in MSTR put skew, surging implied volatility specific to the stock, and further widening discounts in STRC would collectively mark a transition from “preparing for volatility” to “pricing a crisis.”
For now, Anchorage Digital’s conclusion is that markets are tense but not in full alarm mode. Investors across crypto and equity markets are hedged, wary, and closely watching Strategy’s next moves – yet the derivatives that most directly express fear of a company-specific collapse remain below historical crisis thresholds. That gap between perception and outright panic is where the Strategy story currently sits.