Quick Read – Ackman initiated a $2 billion MSFT stake in February calling it a compelling value, but shares are already down 17% year to date, leaving him underwater. – MSFT’s Q3 capex jumped 84% to $31 billion, free cash flow fell 3%, and all seven recent insider transactions…
re disposals with zero purchases. – David Tepper’s Appaloosa Management cut its Microsoft position by roughly 82% in the first quarter of 2026, while Bill Ackman’s Pershing Square went the other direction, initiating a brand-new stake of roughly 5.65 million shares worth about $2.09 billion at quarter-end. Ackman started accumulating in February after Microsoft (NASDAQ:MSFT) sold off following fiscal Q2 earnings, calling the stock a “highly compelling valuation” on the strength of Azure and AI
It was his only new buy of the quarter, and the name is also a core holding in Pershing Square USA, giving Ackman dual-vehicle conviction here. So far, Tepper looks like the one positioned correctly. What Ackman Actually Bought, And Why Ackman’s thesis rests on the same engine that has powered Microsoft for three years: cloud and AI.
In the most recent quarter, Azure grew 40%, the Intelligent Cloud segment hit $34.68 billion (+30% YoY), and the AI business surpassed a $37 billion annualized run rate, up 123% year over year. The forward visibility is the part value investors fixate on: commercial remaining performance obligations reached $627 billion, a contracted backlog that stretches multi-year demand into clear sight. The valuation case is also real.