Microsoft's Great Realignment: Ackman's $2.3 Billion Bet Meets a Gates Foundation Exit and a Sweeter OpenAI Deal

Bill Ackman's Pershing Square builds a $2.3B Microsoft stake amid OpenAI pact and depressed valuation, while the Gates Foundation liquidates its last shares for liquidity.

The narrative around Microsoft is undergoing a rapid rewrite. While the Bill & Melinda Gates Foundation Trust quietly liquidated its last 7.7 million shares – a stake worth roughly $3.2 billion – activist investor Bill Ackman was doing the opposite, building a position of nearly $2.3 billion through Pershing Square Capital Management. The signal isn't confusion; it's a structural shift in who owns the stock and why.

Ackman's move, disclosed at roughly 5.65 million shares, came after February's sell-off depressed the stock to around 21 times expected earnings. That multiple, he argued, is "highly attractive" relative to the software giant's historical valuation. To fund the purchase, Pershing Square largely shed its Alphabet position, placing a concentrated bet on Microsoft's AI-driven future.

On the other side of the trade, the Gates Foundation's sale ended a decades-long link between the trust and the company Bill Gates co-founded. The proceeds help fund a planned increase in annual grants to $9 billion by 2026. Gates himself still sits on roughly 103 million Microsoft shares worth about $43 billion, so the divestment is a liquidity move, not a vote of no confidence.

OpenAI Pact Rewrites the Cash Flow Story

The timing of Ackman's entry coincides with a recalibrated commercial relationship with OpenAI. Under the updated terms, Microsoft is set to receive roughly $6 billion in payments during the 2026 calendar year – up from an earlier projection of $4 billion. The deal also secures access to OpenAI's intellectual property and models through 2032, while granting OpenAI more freedom to use competing cloud providers like AWS or Google Cloud. Microsoft retains a first-mover advantage, however, as OpenAI products must still debut on Azure first.

Wedbush analyst Dan Ives, maintaining an "Outperform" rating with a $575 target, called the new arrangement a net positive. TD Cowen set a $540 price target, although the firm cautioned that Azure's near-term growth is being tempered by capacity constraints.

Valuation Anchored by Azure and Copilot

Microsoft shares closed Friday at €362.95, up 3.42% on the day, but still down 10.07% year-to-date. The trailing price-to-earnings ratio of 25.11 sits well below the five-year median of 34.15, and one company-internal model pegs fair value near $550.

Two operational pillars support that view: Azure continues to grow at 40%, while Microsoft 365 Copilot adds a $30-per-user monthly premium. Internally, Microsoft is expanding its own MAI series of language models, with MAI-Transcribe-1 expected to cut GPU costs by as much as 50% versus external alternatives, reducing reliance on OpenAI's infrastructure.

Regulatory Headwinds and Internal Reshaping

The company's expanding AI footprint is drawing scrutiny. Britain's Competition and Markets Authority has opened a new antitrust probe into Microsoft's cloud practices. Meanwhile, the legal tussle between Elon Musk and OpenAI could pull Microsoft executives into the witness box, further magnifying the policy spotlight on AI partnerships.

Closer to home, Microsoft is streamlining its workforce. LinkedIn will cut around 5% of its staff, affecting about 875 roles in engineering, product, and marketing – part of a broader reallocation of capital toward AI infrastructure and automation. On the security front, the company's "MDASH" system recently identified 16 previously unknown Windows vulnerabilities, including four critical remote-code-execution flaws, which were patched in the latest update. A private enterprise testing phase is slated for June.

Technical Check: Recovery Underway, But Not Confirmed

The stock has reclaimed its 50-day moving average of $342.82, though it remains below the 200-day line at $396.86. The relative strength index of 66.4 suggests growing momentum, but not yet enough to call a full reversal. The 100-day average around $359.52 is the immediate support level to watch.

Ackman's conviction and the improved OpenAI economics have injected fresh confidence into a stock that had been rattled by AI spending fears and competitive noise. The second half of the year will be the real test: if Azure can accelerate through the capacity bottlenecks, the valuation story gains operational backing. Until then, the battle for Microsoft's narrative is being fought in the shareholder register – and for now, the buyers have the upper hand.