Michael Saylor spent another billion dollars betting Bitcoin has bottomed, but prediction markets are pricing a 57% chance he is wrong.

Strategy (NASDAQ:MSTR) disclosed in an April 13 filing that it acquired 13,927 Bitcoin (CRYPTO: BTC) between April 6 and April 12 at an average price of $71,902, funded entirely through its Stretch preferred stock (NASDAQ:STRC).

The company now holds 780,897 BTC at an average cost of $75,577.

Saylor Has Been Calling The Bottom

At a Mizuho investor event earlier this month, Saylor said Bitcoin “likely bottomed around $60,000,” framing the current drawdown as forced-seller exhaustion rather than a sentiment reset.

He doubled down this week on crypto podcast Bankless. “I haven’t seen anything to shake my confidence yet,” Saylor said, calling the asset oversold and predicting it closes 2026 materially higher.

So far, the call has held. Bitcoin bottomed near $60,000 during the Iran conflict and was trading above $75,400 on Friday, its highest level since early February.

He also laid out his longest-dated call yet, telling the show Bitcoin is heading to “20 million, 21 million a coin” over a 21-year horizon. The math implies a 29% compound annual return and a $400 trillion market cap.

Polymarket Disagrees

A Polymarket 2026 contract prices a 57% chance Bitcoin touches $55,000 or lower at some point this year, and a 22% chance it trades as low as $35,000. The $100,000 outcome sits at 40%, and $150,000 at 10%.

The signal is not that Saylor is wrong on the long-term trajectory. It is that the $1 billion he deployed at $71,902 may have been early.

The Stretch Machine Keeps Buying Either Way

Saylor said that miners only produce about $10 billion of new Bitcoin per year at current prices. Strategy’s remaining $49 billion in firepower is nearly five years of that supply, and the company plans to deploy it by December.

He went on to tell Bankless that Strategy is now in “the credit stage,” describing Stretch as a Bitcoin-backed money market aimed at retail savers.

His pitch for the product is simple. “Fix the money, fix the world,” Saylor said, arguing banks could one day resell STRC-style yield as 8% dollar deposits to retail customers.

Not everyone is buying the pitch. YouTube investigator Coffeezilla dismantled STRC in a video this week, accusing Strategy of “leading people like a pied piper” and warning that “you give them $100, they have no obligation to pay you back.”

Coffeezilla drew comparisons to Terra Luna’s collapsed 20% Anchor yield and flagged that 80% of STRC buyers are retail. “It is not suitable for people living paycheck to paycheck. I can’t believe I have to say that.”

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