Peter Schiff’s latest attack on Michael Saylor is not really about whether Bitcoin is money, gold, a bubble, or a religion with better merch. It is about Strategy becoming a leveraged Bitcoin capital structure with a growing line of claimants ahead of common shareholders.
The pressure point is narrower and more testable: if Strategy’s preferred shares stay below par, if its common stock trades near or below Bitcoin net asset value, and if Bitcoin remains weak, the company’s old flywheel turns into a funding problem.
Strategy’s June 29 capital framework shows why the debate has changed. The company authorized a BTC Monetization Program that allows Bitcoin sales to raise up to $1.25 billion for its USD Reserve, fund preferred dividends and debt interest, replenish reserves, or finance repurchases of preferred and common stock. That is a major shift for a company built around accumulation rather than monetization.
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Saylor framed the shift as discipline, not retreat.
“Strategy remains committed to Bitcoin as its primary treasury reserve asset,” Saylor said in the company’s statement. “At the same time, Digital Credit requires liquidity, discipline, and active capital management.”
Schiff’s answer is that the new flexibility is also the tell. If the model still worked cleanly through common equity and preferred issuance, Strategy would not need a formal framework for selling Bitcoin to support the securities built on top of it.
The STRC problem
The flashpoint is Strategy’s Variable Rate Series A Perpetual Stretch Preferred Stock, traded as STRC. It was designed around a $100 stated amount and a variable dividend mechanism. Strategy said the preferred dividend rate would rise to 12.00% for semi-monthly periods with record dates on or after July 1, 2026, while its broader framework included a $2.55 billion USD Reserve and buyback authorizations for preferred and common securities.
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That matters because Schiff’s critique rests on the difference between “designed to trade near $100” and “guaranteed to trade near $100.”
In an interview, Schiff argued that the preferred-stock structure can become a trap if Strategy stops raising new capital or if Bitcoin weakens.
“If they suspend it, it compounds at the rate that it was at when they suspended it,” Schiff said of unpaid preferred dividends. “So it still becomes an obligation that would have to be satisfied in liquidation of the company.”
The market has already started pricing that risk. STRC has traded well below its $100 stated amount, with Coindesk reporting it around $73 last week and Strategy’s own STRC page recently showing prices well below par.
MSTR recently traded at $86.93, while Bitcoin traded near $59,089.
Schiff’s case: “He is destroying his own company”
Schiff’s central claim is that Strategy’s structure depends on a rising Bitcoin price and continuing investor appetite for Strategy securities.
In the interview, he argues that Strategy’s recent Bitcoin purchases reduced Bitcoin per share, that selling common stock below net asset value harms common shareholders, and that selling Bitcoin to meet obligations could pressure the very asset supporting the structure.
“He is destroying his own company to avoid having to sell Bitcoin because he knows if he tries to sell Bitcoin, the price is going to crash,” Schiff said.
Strategy disclosed on May 25 that it had 843,738 BTC, $6.7 billion in convertible notes, $15.5 billion in preferred stock notional, and an $871 million USD Reserve after a $1.5 billion repurchase of 0% convertible notes due 2029.
By June 29, the company had moved to a $2.55 billion USD Reserve and a formal Bitcoin monetization capacity of up to $1.25 billion.
Schiff’s stronger point is not timing; it is convexity. If Bitcoin falls, common equity weakens. If common equity weakens, issuing stock becomes more dilutive. If preferred shares trade below par, new preferred issuance becomes harder or more expensive. If Bitcoin must be sold into weakness, the company’s reserve asset becomes a funding source rather than only a growth engine.
Saylor’s case: “The best credit instrument in the world”
Saylor’s side is not simply “Bitcoin goes up forever,” although Strategy’s model is obviously more powerful when Bitcoin rises.
The company’s official position is that it is building a Bitcoin-focused capital management platform, not merely hoarding coins. Strategy says it can issue securities when capital is attractive, repurchase securities when discounted, manage a USD Reserve, and use Bitcoin monetization when doing so is better than selling common equity.
That is the practical defense: the company is adapting.
READ: Saylor: I Said You, Not The Company, Should Never Sell Bitcoin
Saylor has also tried to reposition the discussion around digital credit rather than only Bitcoin accumulation. After Strategy sold 32 Bitcoin earlier this year, Coindesk reported that Saylor wrote, “Our goal is to make STRC the best credit instrument in the world.”
The bull case is that Strategy’s capital stack is not a fragile bet but a financial machine tied to a scarce digital asset. If Bitcoin rises materially, the value of the company’s holdings increases, credit confidence improves, preferred securities recover, and common dilution becomes less painful or unnecessary.
That is why Schiff and Saylor keep talking past each other. Schiff is underwriting a downside liquidity spiral. Saylor is underwriting Bitcoin appreciation and capital-market flexibility.
The market is now forcing both theories onto the same scoreboard.
Bitcoin price to stock confidence
The issue now is whether Strategy’s—well, strategy—can fund obligations, defend preferred-stock confidence, avoid destructive dilution, and preserve common shareholder value during a prolonged Bitcoin drawdown.
Reuters reported that Strategy’s enterprise value fell below the value of its Bitcoin holdings for the first time, with mNAV at 0.99, while the company faced pressure from falling Bitcoin prices and weaker sentiment around its securities. Barron’s reported that Strategy’s shift toward Bitcoin sales, reserves, buybacks, and a higher STRC dividend marked pressure on the Bitcoin treasury company model.
Those developments cut both ways. For bears, selling Bitcoin marks a retreat from the old never-sell narrative. For bulls, it is rational treasury management under stress.
Schiff’s legal claims are the least certain part of the debate, arguing that investors may sue if they bought STRC as a safe income product.
“I heard Michael Saylor on CNBC,” Schiff said, role-playing a potential investor claim. “He assured me that it was safe. He assured me that it was appropriate for retirees who need income.”
The strongest factual question is simpler: did investors understand that STRC was a cumulative perpetual preferred security tied to Strategy’s board discretion, Bitcoin volatility, market liquidity, and a company whose legacy software business is no longer the main economic story?
The filings gave risk disclosures. Schiff argues public promotion may still create exposure if investors heard a safer message than the documents actually supported. That gap between disclosure and marketing is where future legal scrutiny, if it develops, would likely live.
At about $59,000 Bitcoin, Strategy’s model is under pressure but not mechanically broken. At much higher Bitcoin prices, Saylor’s structure can recover credibility quickly. At much lower Bitcoin prices, Schiff’s warnings about dilution, forced monetization, and preferred-stock stress become harder to dismiss.
That is why the debate has moved from “Bitcoin good or bad” to something more consequential for investors: who owns the upside, who absorbs the downside, and who gets paid first when the treasury asset stops carrying the whole story.
