Share
The argument between Peter Schiff and Michael Saylor has never been polite, but it has rarely been this specific. With Strategy’s shareholders preparing to vote on a proposal to shift STRC dividend payments from monthly to twice-monthly, Schiff has sharpened his line of attack from general Bitcoin (BTC) skepticism to a pointed question about the mechanics of a financial structure he insists is unsustainable.
The dispute has its roots in Strategy’s Q1 2026 earnings call, where Saylor made a remark that reverberated through the crypto community. Saylor told investors that the company may sell some Bitcoin if needed to fund dividend payments on its preferred shares, describing the approach as a way to inoculate the market — language that caught observers off guard from a man who once told followers: “Sell a kidney if you must, but keep the Bitcoin.”
Vote to make $STRC better. pic.twitter.com/gS58ZbszhT
— Michael Saylor (@saylor) May 26, 2026
Schiff quickly challenged the explanation. He said Saylor later softened his earlier comments by claiming Strategy would only sell Bitcoin while remaining a net buyer overall. Schiff argued that the approach only works if Bitcoin can consistently be sold at prices above the company’s average purchase cost, something he believes becomes difficult in a flat or falling market.
Strategy reported a $12.54-billion net loss in Q1 2026 and holds 818,334 BTC at an average purchase price of $75,537 per coin. The company carries about $1.5 billion in annual dividends and debt obligations. Those two facts sit in uncomfortable proximity when Bitcoin is trading near its cost basis.
Strategy has maintained STRC’s 11.5% annualized dividend rate, and its daily trading volume has surpassed $380 million, with Saylor citing approximately 3% volatility and strong institutional participation as evidence of the instrument’s resilience.
Saylor’s mathematical counter to Schiff is straightforward: With $3.2 billion of STRC sold in April generating roughly $80 million-$90 million in monthly dividend obligations, Strategy only needs Bitcoin to appreciate 2.3% annually to finance payments indefinitely. He has also pushed back on the Ponzi characterization directly, arguing Strategy’s own purchases are too small to meaningfully move the Bitcoin market.
Schiff’s sharpest claim is not about the present but about what he expects to happen under stress. He predicted that when the moment arrives and Strategy can no longer sustain STRC dividend payments, Saylor will choose to suspend the dividend and allow STRC to collapse rather than sell Bitcoin from the company’s reserves, arguing that protecting the underlying Bitcoin position matters more to Saylor than honoring obligations to preferred shareholders.
You're running out of cash. What will you sell next to keep the wheels from falling off?
— Peter Schiff (@PeterSchiff) May 26, 2026
In Schiff’s framing, public pledges to defend the dividend serve as a necessary tool to extend confidence in the structure for as long as possible, with the appearance of commitment keeping the model functioning even as its financial foundation grows more fragile.
Strategy is proposing to shift to two scheduled dividend payment dates per month rather than one, arguing the change is intended to increase price stability by helping STRC trade closer to its target $100 par value and dampen the cyclicality caused by a single large monthly payment.
Institutional holders appear aligned with management. Anchorage Digital confirmed it would vote in favor, citing conviction in STRC as a treasury asset and alignment with bi-monthly cash flows. Apyx, described in filings as the largest STRC holder with about $130 million in shares, also publicly backed the proposal.
The twice-monthly structure does not resolve the underlying question Schiff is raising. It is a mechanical refinement to a financial instrument whose long-term viability depends entirely on Bitcoin’s trajectory. At current prices, the model works. The debate is about what happens if it stops working and who pays first.
Share
preferred on
