Jim Cramer calls Michael Saylor “The Master Poker Player” who never shows his hand

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of Jim Cramer The latest criticism centers on a familiar theme: investors who are waiting Michael Saylor to openly reveal what Strategy (NASDAQ:MSTR) plans to continue.

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

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

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

In a recent appearance on CNBC, Cramer was quoted as saying, “He doesn’t have to fight Michael Saylor. He’ll do whatever it takes, he’s his own Malcolm X. Bitcoin (CRYPTO: BTC). By any means necessary, he will defeat the shorts.”

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Why it matters: Amid this debate, Arkham Intelligence pointed out that Saylor recently set aside a $1.44 billion reserve specifically to cover Strategy’s mandatory and discretionary payment obligations for the next 12-24 months.

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

The implication is clear: Saylor demonstrates financial strength, removes speculation about forced Bitcoin sales, provides liquidity for preferred holders, and builds confidence as Strategy continues its aggressive BTC accumulation strategy.

In other words, the reserve is Saylor planting a flag, proving that it can finance everything it owes without touching Bitcoin’s treasury.

Image: Shutterstock

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This article Jim Cramer Calls Michael Saylor ‘Master Poker Player’ Who Never Shows His Hand originally appeared on Benzinga.com

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