Michael Saylor‘s Strategy Inc. (NASDAQ:MSTR) announced Friday it will repurchase $1.5 billion of convertible debt and listed Bitcoin (CRYPTO: BTC) sales as a potential funding source, sending prediction market odds on a 2026 Bitcoin sale to 92%.

The Polymarket contract was sitting near 23% as recently as late April.

The Filing

Strategy will pay roughly $1.38 billion in cash for $1.5 billion in principal of its 0% convertible notes due 2029, a discount to par. The deal was struck through privately negotiated transactions with certain noteholders, with settlement expected May 19.

Funding will come from cash reserves, proceeds from the company’s at-the-market equity program, “and/or proceeds from the sale of bitcoin,” according to the filing. After cancellation, roughly $1.5 billion of the 2029 notes will remain outstanding.

What Polymarket Is Pricing

The Polymarket contract on whether Strategy sells any Bitcoin by June 30th jumped from 72% to 79%.

The same market gives 92% odds of a sale by year-end, up from 86% earlier this week.

The market had already repriced once on May 5, when Saylor said on the company’s earnings call that Strategy “will probably sell some bitcoin to pay a dividend just to inoculate the market.”

Friday’s filing is the first time the company has put Bitcoin sales in writing as a funding source for a specific transaction.

The Counterargument

Not everyone is convinced Strategy needs to sell. Bitcoin commentator Scott Melker argued this week that Saylor’s sell comments are likely tied to SEC disclosure requirements around the STRC preferred shares rather than a real shift in thesis.

On the other side, Peter Schiff has spent the past two weeks calling STRC a “classic centralized Ponzi,” arguing the dividend model depends on continuous capital inflows and rising Bitcoin prices.

Two hours before announcing the buyback on X, Saylor reposted a video from a creator who said he had retired at 51 and replaced all his bonds with STRC.

MSTR is trading at $181 down roughly 2% today, with Bitcoin trading below $80,000.

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