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Jim Cramer Calls Michael Saylor 'The Master Poker Player' Who Never Shows His Hand

Author: Khyathi Dalal | December 03, 2025 12:35pm

Jim Cramer's newest critique centers on a familiar theme: investors expecting Michael Saylor to openly reveal what Strategy (NASDAQ:MSTR) plans to do next.

What Happened: In an X post on Dec. 2, Cramer argued that Saylor operates more like a "master poker player" — someone who's survived enough crises to earn "nine lives," and who understands the power of misdirection.

According to Cramer, Saylor's real advantage is that he can talk one way while positioning the company another, setting the stage for potential market squeezes precisely because people assume he's being transparent.

The comment drew plenty of attention, with prominent crypto account Autism Capital openly wondering whether Cramer meant this as praise, criticism, or a contrarian signal.

In a recent CNBC appearance, Cramer quoted, "Michael Saylor is not to be trifled with. He will do whatever is necessary, he is the Malcolm X of Bitcoin (CRYPTO: BTC). By any means necessary he will defeat the shorts."

Also Read: ‘We Are Not Bitcoin Traders, We’re Bitcoin Investors,’ Says Strategy CEO Fong Lee

Why It Matters: Amid this debate, Arkham Intelligence highlighted that Saylor recently established a $1.44 billion reserve specifically to cover Strategy's mandatory and discretionary payout obligations for the next 12–24 months.

This move signals confidence in the company's financial strength and its ability to meet obligations without selling Bitcoin.

The implication is clear: Saylor is demonstrating financial strength, eliminating speculation of forced Bitcoin sales, securing liquidity for preferred holders, and reinforcing confidence as Strategy continues its aggressive BTC accumulation strategy.

In other words, the reserve is Saylor planting a flag, proving he can fund everything he owes without touching the Bitcoin treasury.

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Image: Shutterstock

Posted In: $BTC MSTR

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