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Home Analysis

A Major Investor Bets Against the Tide on Strategy Shares

Robert Sasse by Robert Sasse
December 28, 2025
in Analysis, Insider Trading, Trading & Momentum, Turnaround
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Strategy Stock
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The equity of Strategy is currently caught in a storm of extreme volatility, presenting a complex puzzle for the market. In a striking divergence, one institutional investor is making a substantial bullish move even as the share price shows severe technical damage, having lost nearly half its value since the start of the year. This clash between broad market anxiety and a major player’s conviction raises a critical question: has the sell-off gone too far?

A Defensive Pivot in Corporate Strategy

Operationally, Strategy appears to be shifting its focus. The firm, renowned for its aggressive accumulation of Bitcoin, reported no new purchases of the cryptocurrency in the week ending December 21, 2025. Its holdings remain static at 671,268 units. Company leadership is now prioritizing balance sheet strength:

  • Bolstering Reserves: U.S. dollar cash holdings were increased from $1.44 billion to $2.19 billion.
  • Designated Use: Management stated this liquidity is explicitly earmarked for preferred share dividends and debt servicing.
  • No Dilution: The company did not utilize its “at-the-market” share offering program during the mid-December reporting period.

This buildup of a multi-billion dollar buffer signals a more defensive posture, moving away from the prior strategy of leveraged expansion of its digital asset portfolio.

Hedge Fund Sees Opportunity in Decline

Defying the prevailing downward trend, TB Alternative Assets Ltd. has established a significant new position in Strategy. Recent mandatory exchange filings reveal the investment firm purchased 126,000 shares during the third quarter. This acquisition carries an approximate value of $40.6 million.

Should investors sell immediately? Or is it worth buying Strategy?

The scale of this commitment is notable. With this single purchase, Strategy instantly became the fifth-largest holding within TB Alternative Assets’ portfolio, accounting for 6.1% of the firm’s total assets. Market observers interpret this move as a powerful vote of confidence. The fund seemingly views the steep decline—with shares currently trading roughly 60% below their 52-week high—as a compelling entry point, directly countering the widespread risk aversion seen elsewhere.

Technical and Insider Signals Advise Caution

However, the technical picture for the stock issues clear warnings. The share price recently formed a so-called “death cross,” a pattern where the short-term 50-day moving average falls below the long-term 200-day average. This configuration is traditionally viewed as an indicator of sustained negative momentum. The bearish case is further supported by a year-to-date (YTD) performance showing a loss of 45.69%.

Adding to the cautious outlook, transactions by company insiders present a contrasting narrative to the hedge fund’s buy-in. Verified data indicates that insiders reduced their holdings during the last reporting period, selling 43,177 shares worth approximately $13.5 million.

Conclusion

The path forward for Strategy’s stock is likely to be determined by a tug-of-war between negative chart signals and institutional belief. While the death cross formation and insider sales fuel the bearish argument, the $40 million commitment from TB Alternative Assets expresses fundamental optimism at current price levels. Investors are now watching to see if the accumulated cash reserves exceeding $2 billion will be sufficient to stem the decline and establish a firm price floor.

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Tags: Strategy
Robert Sasse

Robert Sasse

About Dr. Robert Sasse Accomplished economist, entrepreneur, and profound expert in financial markets. Dr. Robert Sasse holds a doctorate in economics and combines academic rigor with practical entrepreneurial experience. His deep expertise in economic relationships and unwavering conviction for a free-market liberal economic order drives his mission to provide investors with well-founded knowledge and guidance.
Areas of Expertise:
  • Economic Theory and Practice
  • Free-Market Economics
  • Entrepreneurship and Business Strategy
  • Investment Philosophy
Dr. Sasse's unique combination of academic knowledge and real-world business experience enables him to provide investors with comprehensive insights that bridge theory and practice.

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