Jim Cramer Calls Michael Saylor a “Master Poker Player” as MicroStrategy Adjusts Targets and Bitcoin Slides
CNBC host Jim Cramer ignited fresh debate around MicroStrategy and its CEO Michael Saylor, suggesting that Saylor may not be as transparent about his Bitcoin strategy as the market believes. During a segment discussing Bitcoin’s dip to $86,700 and MicroStrategy’s share performance, Cramer argued that Saylor could be strategically signaling one thing while preparing to do the opposite.
“Why do people think Michael Saylor is going to tell you what he’s going to do next? This guy has nine lives because he’s a master poker player — and we are all knaves. I think he could engineer a squeeze of a lifetime by going the opposite of what he says.”
— Jim Cramer
The remarks play into Cramer’s enduring meme status as the “Inverse Cramer Indicator,” where markets often seemingly move in the opposite direction of his calls. But this time, his comments focus not on price predictions—but on Saylor’s psychological game and MicroStrategy’s evolving corporate strategy.
MicroStrategy Stock Falls as Bitcoin Dips
As Bitcoin pulled back to the $86,700 range, MicroStrategy (MSTR) shares closed at $171.42, continuing a multi-week downtrend. The decline follows a period where MicroStrategy routinely outperformed Bitcoin itself, thanks to the company’s aggressive Bitcoin strategy and leveraged balance-sheet approach.
MicroStrategy now holds 650,000 BTC, worth roughly $56 billion as of early December 2025. The company’s average purchase price sits at $74,436 per coin, meaning that even with the current dip, the firm is still substantially in profit.
During this week’s volatility, MicroStrategy quietly added 130 more BTC, reaffirming its conviction even as critics claim the company is overstretched.
MicroStrategy Lowers 2025 Targets and Opens Door to Bitcoin Sales
For the first time in years, MicroStrategy signaled that it may adjust its operational targets downward.
The company told investors that its 2025 goals were being revised lower, citing:
market-wide liquidity tightening
Bitcoin’s correlation to macro events
slower-than-expected enterprise demand
More controversially, the company acknowledged that selling some Bitcoin remains a last-resort option if MicroStrategy’s share price lags too far behind the value of its Bitcoin holdings.
This admission is notable because Saylor has long maintained that MicroStrategy would never sell BTC. Although the company stated such sales are unlikely, the acknowledgement has stirred speculation about whether Saylor’s strategy is shifting.
This nuance is exactly what Cramer seized on.
“Master Poker Player”: Why Cramer Thinks Saylor Is Playing 4D Chess
Cramer’s comments suggest a belief that Saylor's public persona—ultra-bullish, diamond-handed, unwavering—may mask a more dynamic internal strategy.
According to Cramer, Saylor:
may signal one direction while preparing to move in another
understands how his public statements influence market psychology
could engineer a short squeeze by misleading overly bearish traders
historically makes bold moves that contradict market expectations
Cramer argues that people take Saylor too literally:
“This guy’s a master poker player. He doesn’t play checkers—he plays poker.”
This resonates with a long-standing market perception: MicroStrategy under Saylor behaves more like a high-leverage crypto hedge fund than a software company.
Strategy’s Bitcoin Strategy
MicroStrategy is now the world’s largest corporate holder of Bitcoin—by far—owning more than:
Tesla
Marathon Digital
Hut 8
Galaxy Digital
Coinbase
The nation of El Salvador
The company has financed its Bitcoin purchases through:
convertible notes
equity offerings
debt restructuring
operational revenue
strategic treasury allocation
The result is a company whose valuation is deeply tied to Bitcoin’s price. When Bitcoin rallies, MSTR often rallies harder. When Bitcoin falls—like it has in early December—MicroStrategy can underperform sharply.
This volatility is the hallmark of Saylor’s approach: outsized upside, outsized risk.
Cramer’s point is that Saylor may be more agile than he appears.
What Analysts Are Watching Next
Market analysts are focusing on several key factors:
1. Bitcoin’s short-term support at $80,000–$85,000
A breakdown below $80K could trigger more liquidations.
2. MicroStrategy’s next BTC purchase
If Saylor buys aggressively, it reaffirms the long-term thesis.
If he pauses, it signals caution.
3. BOJ decision on December 18–19
A rate hike could strengthen the yen, unwind more carry trades, and add downward pressure to Bitcoin and MSTR.
4. Equity performance vs. Bitcoin holdings value
If MSTR trades at too large a discount, pressure may increase to sell BTC.
5. Saylor’s public commentary
Investors increasingly dissect every word for hidden meaning.
The Bigger Picture: Saylor Is Still Playing Offense
Despite market noise, MicroStrategy continues to position itself as a long-term Bitcoin operating company. Its occasional small buys—like the recent 130 BTC purchase—signal continued conviction, not hesitation.
Cramer’s comments amplify what many insiders already believe:
Saylor is unpredictable, strategically opaque, and fully aware of his influence on markets.
Whether he is actually playing “master poker player” or simply executing an unwavering Bitcoin accumulation strategy, the market continues to react sharply to both his actions and his silence.
