Jim Cramer calls Michael Saylor ‘The Master Poker Player’ who never shows his hand

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Jim Cramer’s The latest criticism centers on a familiar theme: expecting investors Michael Saylor To reveal what openly Strategy (NASDAQ: MSTR ) plans to do next.

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

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According to Cramer, Saylor’s real advantage is that he can talk one way while positioning the company another, setting the stage for a potential market squeeze as people perceive him to be transparent.

The comment attracted a lot of attention, with major crypto account Autism Capital openly wondering if Cramer meant it as praise, criticism, or a contradictory signal.

In a recent CNBC appearance, Cramer was quoted as saying, “Michael Saylor is not to be underestimated. He’ll do whatever it takes, he’s Malcolm X. Bitcoin (CRYPTO: BTC). Either way he’ll beat the shorts.”

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Why this is important: In the midst of this debate, Arkham Intelligence highlighted that Saylor recently established a $1.44 billion reserve to cover the strategy’s mandatory and discretionary payment obligations for the next 12-24 months.

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

The implication is clear: Seller is demonstrating financial strength, eliminating speculation of a forced bitcoin sale, securing liquidity for preferred holders, and bolstering confidence as the strategy continues its aggressive BTC accumulation strategy.

In other words, the reserve proves that the seller can fund everything they owe without touching the bitcoin fund, planting a flag.

Image: Shutterstock

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