New York, May 21, 2026, 18:02 EDT
Pershing Square, run by Bill Ackman, sold its longtime Alphabet position and bought Microsoft after the software giant’s shares fell. Ackman used proceeds from the Alphabet sale to back the new buy. The move puts Pershing Square on the bullish side of the market debate on Microsoft’s AI spending.
Pershing’s new 5.65 million-share Microsoft stake runs counter to recent market moves. Alphabet has led megacap tech this year, with Microsoft’s biggest cloud competitors posting quicker gains in the last few quarters.
Filings carry a warning for investors. A Form 13F offers a quarterly look at big fund managers’ long positions in U.S. stocks, but skips short bets and may not reflect what’s in the portfolio today.
Pershing Square’s latest 13F showed a Microsoft stake worth about $2.09 billion in the first quarter, Barron’s reported. The fund slashed its Alphabet position by 95% and sold out of Hilton Worldwide, but lifted its Amazon stake by 19%. At quarter-end, the largest holdings for Pershing Square were Brookfield, Amazon, and Uber.
Ackman is one of several managers trading around similar names. Daniel Loeb’s Third Point did the opposite in the first quarter, dumping 925,000 Microsoft shares and picking up 175,000 Alphabet shares. Filings reviewed by Reuters also show that both Pershing and Third Point started new positions in Meta Platforms.
Microsoft reported a 40% jump in revenue from Azure and other cloud services in its fiscal third quarter. Microsoft Cloud revenue hit $54.5 billion. CEO Satya Nadella said AI agents moving into software represent “one of the most consequential platform shifts.” Microsoft
Alphabet isn’t on shaky ground. Sundar Pichai, CEO of Alphabet and Google, said Google Cloud revenue jumped 63% to over $20 billion in the first quarter. Backlog almost doubled to more than $460 billion. He pointed to AI product and infrastructure demand as the main driver for the cloud growth.
Amazon is putting on more pressure. The company reported AWS sales up 28% at $37.6 billion for the first quarter. CEO Andy Jassy called it the cloud unit’s “fastest growth in 15 quarters,” citing AI demand and custom chips as drivers. Amazon
The Microsoft bet has its risks. If AI spending doesn’t drive enough margin growth, or if new AI tools chip away at the Microsoft 365 business, the trade could falter. Chris Hohn’s TCI Fund has trimmed Microsoft and added to Alphabet, pointing to “uncertainty over Microsoft’s competitive position.” QuotedData’s Matthew Read said Pershing’s buyback plan probably won’t do much to narrow its discount. QuotedData
Pershing Square Holdings is facing some pressure too. The London-listed fund’s website puts its net asset value at $79.71 per share as of May 19. So far this year, that’s a return of negative 6.4%.
Microsoft ended regular trading at $419.09, slipping less than 1%. Alphabet Class A closed at $387.66, also just below its last finish. After hours, Amazon moved higher, and Meta ticked up as well.
Ackman’s bet is clear and carries risk: Microsoft’s push into AI and higher spending have to drive stronger cloud, software, and Copilot sales sooner than the Street is expecting. Rival tech giants Alphabet and Amazon aren’t standing still.
