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Ackman Repositions Pershing Square to Make Microsoft Its Biggest AI Cloud Bet

The firm shifted its Q2 holdings to favor Azure’s scale and stronger free cash flow as it reduces exposure to Amazon and exits Alphabet.

Overview

  • Pershing Square’s Q2 filings show it trimmed roughly 25% of its Amazon stake, sold its entire Alphabet position, and bought about 553,000 additional Microsoft shares to make Microsoft the largest AI-exposed holding.
  • After the moves Pershing held roughly 6.2 million Microsoft shares valued near $2.3 billion, representing about 11.9% of the portfolio, and retained a sizable Amazon position of more than 8.56 million shares worth about $2 billion or 10.5% of the portfolio.
  • Ackman’s letter and Pershing reports cite Microsoft’s fiscal strength — about $100 billion in Azure revenue for the year and roughly $19.6 billion in free cash flow — as a defensive complement to AI growth.
  • Pershing kept Amazon exposure because it expects AWS demand to rise even as Amazon ramps capital spending to about $220 billion to build data centers, noting AWS revenue growth has accelerated to over 30% in 2026 and Amazon retail unit volume hit about 15% growth in the prior quarter.
  • The trades highlight a central investor tradeoff: backing scale and near-term cash generation at Microsoft versus backing AWS’s market-share gains that require heavy AI infrastructure capex, and they make Pershing’s concentrated view a signal other large investors will watch closely.