New York, May 21, 2026, 18:02 EDT
Bill Ackman’s Pershing Square has swapped a long-held Alphabet stake for Microsoft, buying into the software maker after a selloff and using shares of Google’s parent to help fund the move. The shift puts one of Wall Street’s most-watched stock pickers on the bullish side of a debate over Microsoft’s artificial intelligence spending.
The trade matters now because it cuts against recent market momentum. Pershing built a 5.65 million-share Microsoft position while Alphabet has been one of the stronger megacap technology stocks this year, and Microsoft’s cloud rivals have shown faster growth in recent quarters.
The filings also come with a warning label. A Form 13F is a quarterly snapshot of long U.S. equity holdings by large institutional managers; it does not show short positions and can already be out of date by the time investors read it.
Barron’s reported that Pershing’s first-quarter filing showed a roughly $2.09 billion Microsoft stake, while the fund cut its Alphabet position by 95%, exited Hilton Worldwide and raised its Amazon holding by 19%. That left Pershing with a concentrated book led by Brookfield, Amazon and Uber at quarter-end.
Ackman is not alone in reshuffling the same group of stocks. Daniel Loeb’s Third Point went the other way in the first quarter, selling 925,000 Microsoft shares and buying 175,000 Alphabet shares, while both Pershing and Third Point opened new positions in Meta Platforms, filings reviewed by Reuters showed.
Microsoft’s own numbers give Ackman something to point to. The company said Azure and other cloud services revenue rose 40% in its fiscal third quarter, while Microsoft Cloud revenue reached $54.5 billion; Chief Executive Satya Nadella called it “one of the most consequential platform shifts” as AI agents spread through software. Microsoft
Alphabet’s case is not weak. Sundar Pichai, chief executive of Google and Alphabet, said Google Cloud revenue rose 63% to more than $20 billion in the first quarter, with backlog nearly doubling to more than $460 billion, and that cloud growth was driven by demand for AI products and infrastructure.
Amazon adds another pressure point. The company said AWS sales rose 28% to $37.6 billion in the first quarter, and Chief Executive Andy Jassy called it the unit’s “fastest growth in 15 quarters,” helped by AI demand and custom chip work. Amazon
But the Microsoft trade can go wrong if AI spending fails to produce enough margin expansion, or if AI tools weaken the grip of Microsoft 365, the office-productivity suite used by companies. Chris Hohn’s TCI Fund cut Microsoft and lifted Alphabet, citing “uncertainty over Microsoft’s competitive position,” while QuotedData analyst Matthew Read said Pershing’s separate buyback plan was unlikely to move its discount much. QuotedData
Pershing Square Holdings has had pressure of its own. The London-listed fund showed a net asset value of $79.71 a share as of May 19, with a year-to-date return of minus 6.4%, according to its website.
Microsoft last traded at $419.09, down less than 1% from the prior close, while Alphabet Class A shares were at $387.66, also slightly lower, after the U.S. market close on Thursday. Amazon was higher and Meta also edged up.
That leaves Ackman with a clean but risky call: Microsoft’s AI-heavy spending must turn into durable cloud, software and Copilot revenue faster than investors now expect. Alphabet and Amazon are not waiting around.
