Gates’ foundation sold all of its Microsoft shares. Bill Ackman is loading up on the stock. What is Wall Street missing?

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The Philanthropic Logic Behind the Exit

The total divestment of Microsoft shares by the Bill & Melinda Gates Foundation Trust marks the end of a symbolic and financial era. For decades, the software giant’s equity served as the primary engine for one of the world’s largest philanthropic organizations. According to The Economic Times, Microsoft stock once accounted for nearly 27% of the foundation’s holdings in 2022. This was not a sudden panic sell, but a structured wind-down. The trust began reducing its concentrated position in late 2023, accelerating the process in 2025 when nearly 65% of its holdings were offloaded. The final 7.7 million shares represent the last tranche of a two-year exit that originally began with 28.5 million shares. The driver is liquidity, not a lack of confidence in the company’s trajectory. In May 2025, it was announced that the foundation intends to sunset its operations by 2045, planning to spend more than $200 billion over the next two decades to tackle global inequities.

“There are too many urgent problems to solve for me to hold onto resources that could be used to help people. That is why I have decided to give my money back to society much faster than I had originally planned.”

Bill Gates

Bill Ackman’s Alphabet-to-Microsoft Swap

While the foundation was exiting, Pershing Square Capital Management was entering. In a move reported by Yahoo Finance, CEO Bill Ackman announced a new Microsoft position just hours before the Gates filing hit the SEC on May 15. Pershing’s 13F filing revealed a position of roughly 5.65 million shares, valued at approximately $2.09 billion at the end of the quarter. To fund this acquisition, Ackman liquidated holdings in Alphabet, the parent company of Google.

“To be clear, our sale of $GOOG was not a bet against the company. We are very bullish long term on Alphabet. But at current valuations and in light of our finite capital base, we used $GOOG as a source of funds for $MSFT.”

Bill Ackman Ackman began stockpiling the stock in February, capitalizing on a dip following the company’s fiscal Q2 2026 earnings. This suggests a tactical play on valuation rather than a broad market shift.

AI Adoption Friction and the $190 Billion Bill

Wall Street’s hesitation around Microsoft stems from a disconnect between AI hype and actual commercial conversion. Despite the massive infrastructure push, the adoption of Copilot has been slower than some analysts anticipated. The numbers reveal a challenging climb:

• Conversion Rate: Only 15 million of 450 million paid Microsoft 365 commercial seats have been converted into paying Copilot users.
• Market Share Erosion: Independent research indicates Copilot’s market share dropped from 18.8% in July 2025 to 11.5% by January 2026.
• Capex Pressure: Microsoft is committing $190 billion to capital expenditure in 2026.

This friction has already triggered internal volatility. In March, CEO Satya Nadella reorganized the AI division and sidelined an AI executive who had been recruited with a $650 million payment. For skeptics, the massive capex bill combined with lagging user conversion creates a precarious mathematical equation.

The Resilience of the Microsoft Moat

Despite the AI-related turbulence and a year-to-date stock decline of about 13%, the company’s fundamental financial engine remains formidable. According to Yahoo Finance, Microsoft generated $281 billion in trailing revenue and $149 billion in operating income. The company’s growth is not solely dependent on generative AI. Azure continues to grow at a double-digit pace, and the broader enterprise ecosystem—including LinkedIn, GitHub, and Microsoft 365—creates high switching costs for corporate clients. Recent performance data suggests the core business is still accelerating. As reported by The Globe and Mail, the most recent quarterly report showed revenue increasing 18% to $82.9 billion, with diluted earnings per share and net income growing by 23%. The divergence between Bill Gates’ exit and Bill Ackman’s entry highlights two different types of capital. For the Gates Foundation, the priority is the immediate liquidation of assets to fund urgent global health and poverty initiatives. For the institutional investor, the current valuation—compressed by AI skepticism—presents a buying opportunity in a company that remains deeply embedded in the global economy.