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Why Bill Ackman is betting on Microsoft as AI fears hammer the stock

by May 15, 2026
written by May 15, 2026

Billionaire investor Bill Ackman revealed Friday that Pershing Square has built a new position in Microsoft.

He argued that recent weakness in the software giant’s stock has created an attractive long-term investment opportunity despite growing concerns over artificial intelligence competition and heavy spending.

Ackman disclosed the investment in a post on social media platform X, describing Microsoft as a company trading at a “highly compelling valuation.”

He said Pershing Square began accumulating shares in February after Microsoft’s stock declined following weaker-than-expected December-quarter results.

Microsoft shares (MSFT) have fallen more than 13% this year and remain well below their highs from late last year as investors reassess the company’s AI spending plans, cloud growth outlook, and evolving relationship with OpenAI.

The stake is expected to be formally disclosed in a regulatory filing later Friday.

Ackman sees value in Microsoft’s AI position

Ackman framed Microsoft as one of several technology investments Pershing Square has made during periods when Wall Street became overly concerned about near-term risks.

In his post, Ackman highlighted Microsoft’s Azure cloud-computing platform and its Microsoft 365 software suite as two of the company’s most valuable businesses.

The Microsoft 365 ecosystem includes products such as Excel, Word, and the company’s Copilot artificial intelligence assistant, which is priced at roughly $30 per month for enterprise users.

“We will disclose a new position in Microsoft, a company we have followed for many years now offered at a highly compelling valuation,” Ackman said, adding that Pershing had now made Microsoft a “core holding.”

Ackman also argued that investors were underestimating the durability of Microsoft’s enterprise software business.

He said investors “underestimate the resilience” of the Microsoft 365 subscription suite, “given its deeply embedded role across enterprises and highly attractive price-value proposition.” 

Microsoft has spent aggressively to expand its AI infrastructure and cloud capabilities as competition intensifies across the technology sector.

The company recently outlined plans to spend approximately $190 billion during 2026, a figure that has raised concerns among some investors about profitability and return on investment.

Ackman defended the spending plan, describing it as necessary to support future growth.

OpenAI partnership concerns seen as overblown

Much of Wall Street’s recent caution toward Microsoft has centered on its changing relationship with OpenAI and fears that competitors such as Alphabet and Amazon are narrowing Microsoft’s early lead in enterprise AI.

Microsoft’s stock also weakened after investors questioned slowing cloud-computing growth alongside rapidly increasing capital expenditures.

Ackman pushed back against concerns surrounding Microsoft’s revised OpenAI partnership structure, which no longer gives the company exclusive rights to resell OpenAI’s technology through Azure.

“We view Microsoft’s recent decision to restructure its OpenAI partnership not as a concession but as part of a deliberate pivot toward a more open, multi-model architecture that better serves enterprise customers,” Ackman said.

Ackman additionally said Wall Street was failing to fully account for Microsoft’s economic interest in OpenAI, which he estimated was worth “approximately $200 billion.”

OpenAI has reportedly been exploring plans for an initial public offering as early as this year.

Pershing continues technology investment strategy

The Microsoft investment marks the latest large technology bet by Ackman and Pershing Square.

Ackman noted that Pershing previously purchased Alphabet shares in 2022 after concerns emerged that ChatGPT could disrupt Google’s search business.

The firm also bought Amazon shares following last year’s tariff-driven market selloff tied to President Donald Trump’s “Liberation Day” trade measures.

More recently, Pershing established a large position in Meta Platforms after investors reacted negatively to the company’s elevated AI spending forecasts.

Last month, Ackman launched a new stock-picking vehicle called Pershing Square USA, though shares in the fund fell sharply after its trading debut despite strong institutional participation.

The post Why Bill Ackman is betting on Microsoft as AI fears hammer the stock appeared first on Invezz

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