Key Takeaways
- • Bill Ackman's Pershing Square accumulated approximately $2.4 billion in Microsoft shares beginning in February 2026, capitalizing on a roughly 20% year-to-date decline that pushed the stock to ~$392 per share and below its 200-day moving average of $444.22.
- • Pershing Square has built a second ~$2.4 billion Amazon position since mid-2025, now representing the firm's second-largest holding, based on AWS growth of 28% year-over-year in the March quarter with a 37.7% operating margin and custom silicon commitments exceeding 7GW across OpenAI and Anthropic.
- • The Microsoft entry was justified on valuation grounds, with Ackman arguing the stock had de-rated to 21x forward earnings on what he characterized as overblown competitive concerns in AI and Azure infrastructure durability.
- • Both positions represent a strategic pivot toward mega-cap technology cash cows, funded in part by trimming Ackman's Alphabet position, marking a departure from Pershing Square's historical concentration in consumer and real estate activism.
- • Ackman disclosed both positions ahead of Pershing Square's quarterly 13F filings, with the Microsoft stake described publicly as a "core holding" on the X platform.
Summary
Bill Ackman's Pershing Square Capital Management has executed two substantial positions in mega-cap technology stocks, signaling a strategic reorientation toward artificial intelligence and cloud infrastructure themes. The firm began accumulating Microsoft shares in February 2026 following weakness in the company's fiscal second-quarter report and has built the position to approximately $2.4 billion by the end of May 2026. The entry point proved opportune: Microsoft traded near $392 per share, representing roughly a 20% year-to-date decline and a significant discount to its 200-day moving average of $444.22 at the time of accumulation.
Ackman articulated a valuation-based rationale for the Microsoft position, contending that the stock had compressed to approximately 21x forward earnings amid what he characterized as exaggerated market concerns regarding Azure durability and Microsoft's competitive standing in artificial intelligence. He disclosed the position publicly on X, describing Microsoft as a "core holding" for the fund ahead of its quarterly 13F filing. The Microsoft accumulation was partially funded by trimming Pershing Square's Alphabet position, demonstrating deliberate portfolio reallocation rather than net capital deployment.
The firm's second major technology bet involves Amazon, where Pershing Square has established a roughly $2.4 billion position from scratch since approximately mid-2025, now ranking as the fund's second-largest holding. The Amazon thesis combines valuation attraction with artificial intelligence infrastructure upside. AWS, Amazon's core profit center, delivered 28% year-over-year growth in the March quarter—its fastest rate in 15 quarters—alongside a commanding 37.7% operating margin. The company's custom silicon initiatives, specifically Trainium and Graviton chips, have reached a $20 billion annual run rate, with Amazon having secured landmark capacity commitments including 2GW of Trainium capacity for OpenAI and 5GW for Anthropic.
These positions represent a notable tactical shift for Pershing Square, a fund historically anchored in concentrated, activist-oriented positions within consumer and real estate sectors. The dual mega-cap technology bets underscore Ackman's conviction in cloud computing growth, proprietary silicon competitiveness, and the durability of enterprise artificial intelligence spending. Both stakes were disclosed strategically through official regulatory filings and public communications, ensuring institutional transparency as the positions approached material scale within the fund's capital structure.
Ackman articulated a valuation-based rationale for the Microsoft position, contending that the stock had compressed to approximately 21x forward earnings amid what he characterized as exaggerated market concerns regarding Azure durability and Microsoft's competitive standing in artificial intelligence. He disclosed the position publicly on X, describing Microsoft as a "core holding" for the fund ahead of its quarterly 13F filing. The Microsoft accumulation was partially funded by trimming Pershing Square's Alphabet position, demonstrating deliberate portfolio reallocation rather than net capital deployment.
The firm's second major technology bet involves Amazon, where Pershing Square has established a roughly $2.4 billion position from scratch since approximately mid-2025, now ranking as the fund's second-largest holding. The Amazon thesis combines valuation attraction with artificial intelligence infrastructure upside. AWS, Amazon's core profit center, delivered 28% year-over-year growth in the March quarter—its fastest rate in 15 quarters—alongside a commanding 37.7% operating margin. The company's custom silicon initiatives, specifically Trainium and Graviton chips, have reached a $20 billion annual run rate, with Amazon having secured landmark capacity commitments including 2GW of Trainium capacity for OpenAI and 5GW for Anthropic.
These positions represent a notable tactical shift for Pershing Square, a fund historically anchored in concentrated, activist-oriented positions within consumer and real estate sectors. The dual mega-cap technology bets underscore Ackman's conviction in cloud computing growth, proprietary silicon competitiveness, and the durability of enterprise artificial intelligence spending. Both stakes were disclosed strategically through official regulatory filings and public communications, ensuring institutional transparency as the positions approached material scale within the fund's capital structure.
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