Strategy's Bitcoin leverage game: Wall Street short-selling sniping, large institutions holding shares and betting

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ODAILY
05-16
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Author: Nancy, PANews

As Bitcoin's price returns to the $100,000 level and MSTR's stock price continues to rise, market disagreements about Strategy's (formerly MicroStrategy) valuation are accelerating. On one hand, many global large institutions are quietly increasing their holdings of MSTR stock, viewing it as an important financial instrument for indirect Bitcoin allocation. On the other hand, its high volatility and deeply leveraged asset structure have also attracted the attention of Wall Street short sellers. As Strategy continues to increase its Bitcoin exposure, it is evolving into a bellwether for Bitcoin price trends and a focal point for capital leverage speculation.

Stock Outperforms Tech Giants, Targeted by Wall Street Short Sellers

At the recent New York Sohn Investment Conference, legendary Wall Street short seller and former hedge fund manager Jim Chanos stated that he is shorting Strategy while simultaneously buying Bitcoin, calling it a "$1 buy, $2.50 sell" arbitrage opportunity.

He pointed out that Strategy holds over 500,000 Bitcoins through high leverage, and its current stock price represents a significant premium compared to its actual holdings. He criticized the emergence of companies imitating Strategy, selling the concept of purchasing Bitcoin through corporate structures to retail investors and seeking high valuations, calling this logic "absurd".

Over the past year, MicroStrategy's stock price has risen over 220%, while Bitcoin has only increased by about 70%. Chanos believes this trade is a "barometer" for observing retail speculative behavior.

Chanos is a highly influential investor on Wall Street, known for his deep fundamental analysis and keen ability to identify corporate financial fraud and business model flaws. His classic short-selling cases include Enron, WorldCom, and Luckin Coffee. However, in recent years, he has also suffered significant losses from shorting Tesla, leading some funds to close or adjust their strategies.

Notably, this is not the first time Strategy has been targeted by a prominent short seller. In December last year, the well-known short-selling research firm Citron Research announced shorting Strategy. Although they were bullish on Bitcoin overall, they believed MSTR had significantly deviated from Bitcoin's fundamentals. This news temporarily caused a sharp decline in MSTR, but due to Bitcoin's price increase driving market sentiment and MSTR's inclusion in the Nasdaq 100 index improving market visibility and liquidity, the short attempt ultimately failed.

Recently, in addition to external short-selling pressure, Strategy's executives have been frequently selling their shares. Disclosed information shows that Jarrod M. Patten, who has been a company director for over 20 years, has cumulatively sold approximately $5.2 million in stock since April this year and plans to sell an additional $300,000 this week.

Despite this, MSTR's stock price remains resilient. According to MSTR-tracker data, Strategy's total market value has reached $109.82 billion, ranking 183rd in global asset market value. This year, MSTR has already accumulated a rise of approximately 37.1%, outperforming not only Bitcoin but also tech giants like Microsoft, NVIDIA, Apple, and Amazon.

Q1 Financial Report Shows Over $4.2 Billion Loss, Backed by Over 1,000 Institutions

MSTR-tracker data shows that as of May 16, Strategy holds 568,840 BTC, with a Bitcoin investment return rate of 15.65% year-to-date. Based on the latest data, the estimated Bitcoin earnings per share (EPS) for this quarter is $37.82.

In contrast to the impressive Bitcoin return rate, Strategy's latest quarterly financial performance is under pressure due to Bitcoin's price pullback in the latter part of the first quarter. The company's recently released 2025 Q1 financial report shows a year-on-year revenue decline of 3.6% to $111.1 million, falling short of market expectations. The net loss was as high as $4.23 billion (loss per share of $16.49), significantly exceeding market expectations.

To alleviate financial pressure and further expand its Bitcoin asset exposure, Strategy is accelerating its capital operation strategy. Earlier this month, Strategy announced a new $21 billion public market common stock issuance plan and has raised its BTC return rate target from 15% to 25%, with the BTC dollar return target increasing from $10 billion to $15 billion. Subsequently, Strategy further announced a new "42/42 plan" aimed at raising $84 billion to purchase Bitcoin within two years. Wall Street analysts support this, with Benchmark and TD Cowen analysts reaffirming their buy ratings and believing the capital raising strategy is feasible.

Unlike most company stocks corresponding to product market sales performance, Strategy's stock is positioned as a "smart leverage" for Bitcoin. Its founder Saylor elaborated on this narrative when renaming the company. Between traditional assets (like SPDR S&P 500 ETF and Invesco QQQ Trust, with volatility levels between 15-20) and Bitcoin (with volatility levels between 50-60), there is approximately a 45% difference. Strategy's common stock volatility target is even higher than Bitcoin itself, aiming to reach 80-90, while maintaining what Saylor calls "smart leverage" through a combination of equity issuance and convertible bonds.

Despite short-selling attacks, many large institutional investors are also buying into Strategy's strategy, and recent institutional investment has boosted market confidence. Fintel data shows that to date, 1,487 institutions hold Strategy stock, with a total of 139 million shares, currently valued at approximately $55.175 billion.

Citadel Advisors

Citadel Advisors is one of the world's largest hedge funds. 13F filings show that as of the first quarter of this year, Citadel Advisors held MSTR stocks worth over $6.69 billion, approximately 23.22 million shares, making it one of Strategy's largest shareholders.

Vanguard Group

As of Q1 2025, Vanguard Group, one of the world's largest public fund management companies, holds approximately 20.58 million MSTR shares, valued at over $5.93 billion.

Susquehanna International Group

Susquehanna International Group is a globally renowned hedge fund company. As of the first quarter of 2025, the company holds MSTR stocks worth over $5.73 billion, approximately 19.88 million shares.

Jane Street

13F filings show that as of Q1 2025, Jane Street, one of the world's top hedge funds, holds over 16 million MSTR shares, valued at nearly $4.63 billion.

Capital International

According to Capital International's Q1 13F filing this year, the institution holds nearly 14.68 million MSTR shares, valued at approximately $4.23 billion.

BlackRock

As of the first quarter of this year, BlackRock, one of the world's largest asset management giants, holds approximately 14.42 million MSTR shares, valued at over $4.15 billion.

CalPERS

CalPERS is the second-largest public pension fund in the United States, managing over $300 billion in assets. As of Q1 2025, CalPERS holds 357,000 MSTR shares, valued at approximately $102 million.

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Disclaimer: The content above is only the author's opinion which does not represent any position of Followin, and is not intended as, and shall not be understood or construed as, investment advice from Followin.
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