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Strategy Talks Up 'Disciplined' Bitcoin Sales, But Prediction Markets Are Not Convinced
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Strategy Talks Up 'Disciplined' Bitcoin Sales, But Prediction Markets Are Not Convinced
May 26, 2026 9:05 AM

Strategy Inc ( MSTR ) announced on Tuesday that it had completed the repurchase of $1.5 billion of convertible debt, retiring the principal for roughly $1.38 billion in cash at an 8% discount to par.

The company also issued $2 billion of new preferred stock and $84 million of common stock, then used the proceeds to buy 24,869 bitcoin.

It now holds 843,738 Bitcoin (CRYPTO: BTC) and reported a year-to-date BTC Yield of 13.3%.

President Phong Le said the moves reflected an approach laid out on the company’s first-quarter earnings call, when it pledged to use “the full range of capital management tools available to us, including the disciplined sale of Bitcoin.”

Why Polymarket Thinks Saylor Will Sell

The shift traces back to Strategy’s first-quarter earnings call, when Saylor said the company might “sell some Bitcoin” to fund a dividend, a notable turn for a CEO who once told holders to “sell a kidney if you must, but keep the Bitcoin.”

Polymarket traders price the odds of a Bitcoin sale by May 31 at just 3%. The June 30 contract sits at 33%, and the December deadline at 74%.

With a $15.5 billion preferred stock burden and a $14.46 billion unrealized loss on its bitcoin in the first quarter, Strategy faces a steep annual dividend obligation of roughly $1.5 billion.

Longtime critic Peter Schiff has argued the structure cannot hold, calling the high-yield preferred program a “Ponzi” and predicting Saylor would “suspend the dividend and crash STRC rather than crash Bitcoin.”

What It Means For MSTR Holders

Tuesday’s release answers the near-term version of that thesis. Strategy met its obligations by issuing $2 billion in preferred stock and setting aside an $871 million cash reserve, while cutting convertible debt to $6.7 billion from $8.2 billion. No Bitcoin was sold.

A separate market gives roughly even odds that Strategy reports holding at least 1 million bitcoin by year-end.

Traders appear to expect both continued buying and an eventual, smaller sale, the “inoculation” Saylor described rather than the forced liquidation Schiff predicts.

Image: Shutterstock

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