Jane Street Goes Big on Saylor's Strategy: MSTR Position Up 473%

Jane Street Capital just made one of the loudest institutional bets on Bitcoin without buying a single coin. The quantitative trading giant increased its Strategy (MSTR) holdings by 473%, adding 785,224 shares to reach 951,187 shares valued at roughly $121 million, according to its latest 13F filing with the SEC. For a firm with over $662 billion in reported 13F portfolio positions, this is a clear vote of confidence in Michael Saylor's Bitcoin treasury playbook.

The move puts Jane Street among Strategy's largest shareholders. Across its group entities, the firm holds about 7.3% of the company's Class A common stock, according to Schedule 13G filings.

Why Is Jane Street Betting on Strategy Instead of Bitcoin Directly?

Jane Street is a market-making powerhouse known for quantitative strategies that consistently outperform. The firm doesn't make casual bets. So why MSTR over spot BTC or a Bitcoin ETF?

The answer likely comes down to leverage. Strategy functions as a leveraged Bitcoin proxy. In bull runs, MSTR has historically delivered two to three times BTC's returns because of its debt-fueled accumulation model. For a quant firm looking to maximize exposure with built-in amplification, that math makes sense.

The timing is notable too. Jane Street loaded up during Q4 2025 while Bitcoin and MSTR were both under pressure. Buying the dip at scale is classic institutional behavior, and it signals the firm sees current prices as an entry point rather than a warning sign.

How Big Is Strategy's Bitcoin Stack?

Michael Saylor has turned Strategy, formerly MicroStrategy, from a mid-tier business intelligence company into the world's largest corporate Bitcoin holder. The numbers tell the story.

As of February 22, 2026, Strategy holds 717,722 BTC acquired at an average price of $76,020 per coin for a total cost of about $54.56 billion. That stack represents over 3.4% of Bitcoin's total 21 million supply.

Saylor has funded this through a mix of debt, equity sales, and preferred stock offerings. Last year alone, Strategy issued $7 billion in preferred stock, making it the largest issuer of such securities in the United States. The strategy centers on maximizing "Bitcoin per share," effectively turning MSTR stock into a leveraged bet on BTC appreciation.

The Orange Century

Today, Strategy announced its 100th Bitcoin purchase since the program began in August 2020. The milestone buy added 592 BTC for $39.8 million at an average price of $67,286 per coin, funded through the sale of 297,940 Class A shares via its at-the-market program. Saylor teased the milestone on X with the caption "The Orange Century." He has also stated the company could survive a Bitcoin crash to $8,000 while still covering its $6 billion in net debt.

Who Else Is Piling Into MSTR?

Jane Street's accumulation fits a broader pattern of institutional MSTR buying.

Vanguard index funds purchased a combined $707.5 million in MSTR shares in early 2026, split between its Value Index Fund ($202.5 million) and Mid-Cap Index Fund ($505 million). Worth noting: these were passive purchases driven by index rebalancing rather than active conviction trades, but they still reflect Strategy's growing weight in mainstream equity indexes.

State retirement funds are getting involved too. Virginia's State Retirement Fund added 7,180 shares to hold 31,880 worth $4.1 million, while Louisiana holds 17,900 shares. Even Strategy board member Jane Dietze bought 1,000 preferred shares for $99,485.

The institutional thesis is straightforward: MSTR offers amplified Bitcoin exposure through traditional equity markets, making it accessible for funds that can't or won't hold crypto directly.

What Are the Risks?

The bull case writes itself, but the bear case deserves equal attention.

MSTR vs BTC Performance

MSTR has underperformed Bitcoin significantly, losing over 50% of its value year-over-year. Strategy's market-to-net-asset-value ratio has compressed to around 1.06, down from premiums that previously exceeded 2x, as more institutions shift toward spot Bitcoin ETFs for cleaner exposure. The chart shows lower highs and lower lows, a textbook bearish trend.

What Analysts Are Saying

Canaccord Genuity recently slashed its MSTR price target from $474 to $185, though it maintained its Buy rating. Analyst Joseph Vafi cited Bitcoin's failure to behave like "digital gold" during recent market stress, but still sees roughly 20% upside in BTC during 2026.

For Jane Street, a quant firm built on probability and risk management, these factors are presumably priced into their thesis. But retail investors following institutional moves should understand that MSTR's leverage cuts both ways. It amplifies gains in bull markets and magnifies losses when sentiment turns.

What Does This Mean for Bitcoin?

When one of the world's most sophisticated trading firms increases its indirect Bitcoin exposure by 473%, it sends a signal to the broader market. Jane Street's bet validates Saylor's core argument: Bitcoin belongs on corporate balance sheets.

Whether this marks a floor for MSTR during current volatility or just a well-timed trade from a firm that makes thousands of them daily, the trend is clear. Institutional capital continues flowing toward Bitcoin exposure, and Strategy remains the preferred vehicle for those who want leverage on top.

Sources:

• Phemex Reporting on Jane Street's 473% MSTR holdings increase and share valuations
• CoinDesk Strategy's 100th Bitcoin purchase announcement and updated holdings figures
• Bitcoin Magazine Confirmation of 717,722 BTC total holdings at $76,020 average cost
• Benzinga Canaccord Genuity price target cut from $474 to $185 with maintained Buy rating
• The Street Virginia State Retirement Fund and other state pension fund MSTR holdings
• Odaily Vanguard index fund purchases totaling $707.5M in MSTR shares
• CryptoTimes Jane Street's 7.3% stake and institutional context.