How the Anti-Bitcoin Vanguard Flipped the Script to Become Strategy’s Largest Investor

The Bitcoin naysayers just pulled off the ultimate plot twist—turning into its biggest backers. Here’s how the skeptics got rekt (by their own playbook).

From FUD to fortune

They called it a bubble, a scam, a passing fad. Now? They’re stacking sats like it’s the last lifeboat off the Titanic. The irony’s thicker than a Bitcoin maximalist’s hopium supply.

The pivot heard ‘round Wall Street

When institutional FOMO meets existential FUD, you get this masterclass in cognitive dissonance. The same suits who warned clients about ‘digital Beanie Babies’ now quietly allocate 20% to BTC futures—because nothing screams conviction like hedging your hedge.

Bonus jab: Nothing unites finance bros faster than the smell of missed gains—except maybe a Fed liquidity spigot.

TLDR

• Vanguard holds over 20 million shares of Strategy Inc. (MSTR), worth approximately $9.26 billion, making it the company’s largest institutional shareholder
• The positions come from passive index fund exposure rather than active investment decisions, creating a contradiction with Vanguard’s stated anti-crypto stance
• Vanguard executives have repeatedly criticized bitcoin as speculative and lacking fundamental value, while refusing to offer crypto ETFs to clients
• Strategy, led by Michael Saylor, has converted into a bitcoin holding vehicle with over 600,000 BTC worth about $72 billion
• Market analysts have criticized the disconnect between Vanguard’s public messaging and actual portfolio exposure

Vanguard Group, the $10 trillion asset management giant known for blocking client access to Bitcoin ETFs, has become the largest institutional shareholder of Strategy Inc., a company whose business model centers on buying and holding bitcoin. The investment firm now owns more than 20 million shares of Strategy, representing over 8% of the company and worth approximately $9.26 billion.

This development has created a clear contradiction between Vanguard’s public stance on cryptocurrency and its actual portfolio holdings. The company’s executives have consistently criticized bitcoin as a speculative asset lacking fundamental value. Chief Investment Officer Duncan Burns and other senior leadership have repeatedly emphasized their skepticism regarding digital assets.

CEO Salim Ramji reinforced this position in August 2024, stating that Vanguard would not pursue a crypto ETF. He emphasized the firm’s commitment to “client-focused innovation, not mimicking competitors.” The company continues to block clients from investing in spot bitcoin ETFs, even as competitors like BlackRock have launched successful bitcoin products.

Vanguard’s Strategy holdings come from passive index fund exposure rather than deliberate investment decisions. The shares are distributed across both index-tracking and actively managed funds, including the Total Stock Market Index Fund, the Vanguard Extended Market Index Fund, and the Vanguard Growth ETF. These funds mirror broad stock indices and automatically include companies like Strategy when they meet certain criteria.

Strategy, formerly known as Microstrategy, has transformed itself into a bitcoin holding vehicle under executive chairman Michael Saylor’s leadership. Since 2020, the company has acquired more than 600,000 bitcoin worth approximately $72 billion. The company’s shares have become a proxy for bitcoin exposure, particularly before the U.S. approved spot bitcoin ETFs.

Market Reaction and Criticism

The contradiction between Vanguard’s messaging and portfolio reality has drawn criticism from market participants. Matthew Sigel, head of digital assets research at VanEck, described the situation as “institutional dementia” on social media platform X. He wrote that “indexing into $9 billion of what you openly mock isn’t strategy.”

Vanguard: Bitcoin is immature and has no value.

Also Vanguard: Buys 20M shares of MSTR, becomes top backer of Bitcoin’s loudest bull.

Indexing into $9B of what you openly mock isn't strategy.
It’s institutional dementia. pic.twitter.com/UdPdHoy3Uv

— matthew sigel, recovering CFA (@matthew_sigel) July 14, 2025

Bloomberg analyst Eric Balchunas offered a different perspective, noting that index funds must own all stocks that meet their criteria regardless of personal approval. He described the situation as ironic, stating that “Vanguard chose this life” when deciding to operate passive index funds.

The disconnect extends beyond Strategy holdings. Vanguard also ranks as the largest institutional investor in GameStop Corp., with 39.24 million shares representing approximately 8.77% of the company’s free float. On May 28, 2025, GameStop disclosed a $513 million allocation to bitcoin as a treasury reserve.

Passive Investment Challenges

Vanguard’s situation highlights the challenges faced by passive investment managers in maintaining consistent messaging while following index mandates. The firm’s index funds must hold stocks that meet specific criteria, regardless of management’s personal views on those companies or their strategies.

Strategy’s inclusion in major indices has made it impossible for Vanguard to avoid exposure while maintaining its passive investment approach. The company’s rapid growth and bitcoin accumulation strategy have increased its market capitalization and index weighting.

Current Position

Despite the arrival of CEO Salim Ramji in May 2024, Vanguard has maintained its anti-crypto stance. Ramji emphasized the importance of consistency in firm positioning and product offerings after his appointment. The company continues to refuse offering bitcoin ETFs to clients, even as the iShares Bitcoin Trust became the fastest ETF to manage over $80 billion in assets.

According to recent filings, Vanguard has surpassed Capital Group as Strategy’s top institutional holder. The investment represents one of the largest institutional exposures to bitcoin-related assets, despite the firm’s stated opposition to cryptocurrency investments.