- Ackman, Loeb take different routes on tech bets in early 2026
May 16, 2026
By Svea Herbst-Bayliss
NEW YORK, May 15 (Reuters) - Two of Wall Street's most closely watched billionaire stock pickers, both once voluble activist investors, took opposite tacks this year when Bill Ackman bet on Microsoft and exited Google parent Alphabet and Daniel Loeb did the opposite.
Ackman said on X his firm Pershing Square began building a new position in software giant Microsoft in February after shares dropped, saying investors weren't giving it enough credit for its Microsoft 365 office suite and artificial intelligence investments.
Loeb's hedge fund Third Point, on the other hand, sold 925,000 shares of Microsoft during the first quarter, liquidating a position the firm had held since late 2022, according to a new regulatory filing.
Ackman and Loeb once ranked among Wall Street's loudest activist investors, pushing companies to perform better with suggestions ranging from selling off divisions to firing CEOs.
In recent years, both have adopted a quieter tone, sidestepping public fights that generated headlines, and instead making stock picks and riding along. Picks by the two are closely followed by investors parsing their quarterly filings.
Loeb's Third Point reported it bought 175,000 shares in Google parent Alphabet in the first quarter, while Ackman sold down most of his position in the company, according to a regulatory filing. A source said Ackman exited the rest of his Alphabet holding in the second quarter.
Also during the first quarter, both Pershing Square and Third Point established new positions in Meta Platforms, their filings show. Reuters first reported the position in February when Ackman told clients the technology and social media heavyweight will benefit from artificial intelligence.
The regulatory filings showed Loeb and Ackman and other big investors who filed their quarterly 13F holding data with the Securities and Exchange Commission are being more selective in investing in the "Magnificent Seven" AI giants, a group that includes Meta, Microsoft and Alphabet.
(Reporting by Svea Herbst-Bayliss; Additional reporting by Suzanne McGee; Editing by Tom Hogue)
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- Pershing Square Snapped Up Microsoft Shares, Exited Hilton, Slashed Alphabet Stake in First Quarter
May 15, 2026
Pershing Square Capital Management, the hedge fund run by billionaire Bill Ackman, added Microsoft as a core holding during the first quarter of 2026, betting that the software giant will be a winner in the artificial-intelligence race. Pershing Square held 11 U.S.-listed equity positions with a disclosed market value of about $13.71 billion by the end of the first quarter, according to the fund’s latest 13F filing, which was submitted to the Securities and Exchange Commission on Friday. The top holding was Brookfield , valued at roughly $2.42 billion; followed by Amazon valued at $2.39 billion; and Uber valued at $2.15 billion.
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- Microsoft Stock Jumps After Bill Ackman Reveals New Position
May 15, 2026
This article first appeared on GuruFocus.
Microsoft (NASDAQ:MSFT) stock surged 2% on Friday after a report said billionaire investor Bill Ackman (Trades, Portfolio) added the software giant to Pershing Square's portfolio.
Warning! GuruFocus has detected 1 Warning Sign with MSFT. Is MSFT fairly valued? Test your thesis with our free DCF calculator.
Microsoft has lost more than 15% this year, even after closing at $409.43 in the previous session. Investors have been weighing heavy competition from Amazon and Google, along with Microsoft's plan to spend $190 billion on capital projects in 2026.
Microsoft, meanwhile, still posted quarterly revenue of $82.89 billion, up 18% from a year earlier. Azure grew 40%, and the company also highlighted enterprise demand for its M365 Copilot tools, which it is selling for about $30 a user each month.
Ackman's move fits his usual style of backing a small number of large companies when he sees a long-term opening. Microsoft's recent weakness may have looked like that kind of setup, especially with AI demand still building and the stock trading around 21 times forward earnings.
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- Why Microsoft Stock Is Surging Today
May 15, 2026
Microsoft (NASDAQ: MSFT) stock is solidly in the green on Friday despite a bearish backdrop for tech stocks. The company's share price was up 3% as of noon ET. Meanwhile, the S&P 500 was down 1.2%, and the Nasdaq Composite was off 1.4%. The stock had been up as much as 4.1% earlier in the session.
Microsoft is rising today following news that Bill Ackman's Pershing Square Capital Management had bought shares and sold out of its position in Alphabet. Despite today's pop, Microsoft is still down 13% in 2026 and 22% from its lifetime high.
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Ackman drops Alphabet and buys Microsoft
Pershing Square is a hedge fund founded and run by billionaire Bill Ackman, and it has an impressive track record of success. As a result, some investors pay close attention to what stocks the fund is buying and selling.
With Pershing moving out of Alphabet and into Microsoft, the latter company has gotten a high-profile vote of confidence from a leading investment firm. Ackman cited Microsoft's "highly compelling valuation" on the heels of recent sell-offs as a core reason for backing the stock.
What's next for Microsoft?
Despite strong business results, Microsoft has seen sell-offs this year as some investors have bet that the company faces meaningful disruption risks from other artificial intelligence (AI) players. On the other hand, the tech giant has a very strong position in the AI market and broader software space.
Ackman pointed to Microsoft's strong positioning in cloud-infrastructure services and office productivity software as reasons for Pershing buying the stock, and there are good reasons to think that the company can still deliver long-term wins even though its Copilot software hasn't been as successful as other AI chatbots.
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- Pershing Square Takes Microsoft Stake, Ackman Calls Valuation Compelling
May 15, 2026
This article first appeared on GuruFocus.
Microsoft (NASDAQ:MSFT) rose 0.24% in premarket after Bill Ackman (Trades, Portfolio) disclosed that Pershing Square has been building a position since February, calling its current valuation "highly compelling." The fund established its position at approximately 21x forward earnings, broadly in line with the market multiple and below Microsoft's recent historical average. The full stake size will be disclosed in a 13F filing later today.
Ackman's thesis centers on two core franchises he says account for approximately 70% of Microsoft's profits. M365 serves more than 450 million daily users, and Azure grew 39% in constant currency last quarter with management guiding to modest acceleration in the second half. He acknowledged that investors have been concerned about M365's competitive positioning against AI alternatives including Anthropic's Claude Cowork, and about the durability of Azure's growth given Microsoft's evolving OpenAI relationship. Ackman dismissed both. He also argued that Microsoft's roughly 27% economic interest in OpenAI is not reflected in the headline multiple, which he values at approximately $200 billion, or about 7% of Microsoft's current market capitalization.
Pershing Square USA (PSUS), Ackman's closed-end fund that debuted on the NYSE last month, has also designated Microsoft as a core holding. The position extends a pattern of opportunistic tech buying. Pershing Square acquired Alphabet (NASDAQ:GOOG) after the stock declined on ChatGPT's release in late 2022, Amazon (NASDAQ:AMZN) following Liberation Day, and Meta Platforms (NASDAQ:META) after the market's reaction to its capital expenditure guidance.
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- Bill Ackman Just Made A Massive Tech Stock Bet
May 15, 2026
This article first appeared on GuruFocus.
Bill Ackman (Trades, Portfolio) is making another major bet on Big Tech, revealing that Pershing Square will disclose a new stake in Microsoft (NASDAQ:MSFT) in its upcoming 13F filing while calling the software giant highly compelling at current prices.
Warning! GuruFocus has detected 1 Warning Sign with MSFT. Is MSFT fairly valued? Test your thesis with our free DCF calculator.
Ackman also said his newer fund, Pershing Square USA, has already made Microsoft one of its core holdings, signaling strong conviction even as parts of Wall Street have recently grown more cautious around the company's AI and cloud outlook.
In a lengthy post on X, Ackman argued that Microsoft's recent stock weakness has been driven largely by fears surrounding two issues: whether Microsoft 365 can hold up against increasingly powerful AI workplace tools like Anthropic's Claude Cowork, and whether Azure's growth can remain durable as Microsoft's relationship with OpenAI continues evolving.
But Ackman believes investors are underestimating how deeply embedded Microsoft's ecosystem has become inside large enterprises. He argued that Microsoft 365 is not just another software product, but part of the operational backbone for many companies through its integration across identity management, security, compliance and workflow infrastructure.
Ackman also defended Microsoft's massive AI spending push, saying the company's projected $190B 2026 capex budget should be viewed as long term growth investment rather than reckless spending. He compared Microsoft's AI infrastructure buildout to similar aggressive investments being made by Amazon (AMZN), Alphabet (NASDAQ:GOOG) (NASDAQ:GOOGL) and Meta (META).
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- Is Microsoft undervalued? Why Bill Ackman is buying MSFT at 21x earnings
May 15, 2026
Investing.com -- Pershing Square disclosed a new position in Microsoft Corp (NASDAQ:MSFT) on Friday, with billionaire investor Bill Ackman citing the recent market volatility as an opportunity to acquire what he described as a dominant franchise at an attractive valuation.
Ackman stated that short-term investors have overreacted to temporary headwinds, creating an entry point for long-term investors. He compared this situation to previous investments in Alphabet and Meta during periods of market uncertainty.
The hedge fund manager focused on Microsoft’s enterprise distribution capabilities, noting that M365 and Azure generate approximately 70% of the company’s profits. He highlighted the platforms’ retention rates, which he attributed to their security and compliance infrastructure.
"As two of the largest forces in equity markets converge, we have found occasional opportunities to acquire some of the most dominant long-term compounding franchises at attractive valuations," Ackman said.
M365, with 450 million daily users, serves as the primary platform for enterprise productivity software. Azure continues to benefit from cloud migration, with AI workloads now contributing to growth.
Ackman addressed recent investor concerns regarding competition from AI labs like Anthropic and its Claude Cowork platform. He argued that M365’s integration and pricing structure, at $20 average revenue per user compared to double that for standalone applications, create barriers to replacement.
Regarding Microsoft’s relationship with OpenAI, Ackman viewed the shift toward a multi-model architecture as a strategic advantage rather than a weakness.
"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," he stated.
Pershing Square began purchasing shares in February 2026 following the company’s fiscal second-quarter results. At the time of the initial purchases, Microsoft traded at 21 times forward earnings, below historical averages.
Ackman noted that the valuation does not reflect Microsoft’s approximately 27% economic interest in OpenAI, which he valued at roughly $200 billion based on OpenAI’s most recent funding round.
The investor expressed confidence in Microsoft’s $190 billion capital expenditure budget for 2026, characterizing it as growth investment. He also pointed to the transition from per-seat pricing to metered consumption as a potential revenue driver as AI agents increase platform usage.
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- Bill Ackman's Pershing Square discloses Microsoft stake, touts ‘deeply embedded' software
May 15, 2026 · nypost.com
Ackman, 60, wrote in a lengthy X post that Microsoft operates “two of the most valuable franchises in enterprise technology” in the form of its 365 productivity apps, which include Word and Excel, and its Azure cloud-computing business.
- Billionaire investor Bill Ackman is suddenly bullish on OpenAI partner Microsoft
May 15, 2026
Warren Buffett disciple Bill Ackman has gone fishing for value again, and he’s bringing back a new catch: beaten-up shares of Microsoft (MSFT).
The news: Ackman said in a new X post on Friday morning that his hedge fund Pershing Square (PS) will disclose a new position in Microsoft in a 13F filing later on Friday. He added that Microsoft is “a company we have followed for many years now offered at a highly compelling valuation.”
“We began building our position in MSFT in February following a meaningful share price decline after the company reported its fiscal Q2 2026 results,” Ackman explained. “We were able to establish our position at a valuation of 21 times forward earnings, broadly in line with the market multiple and well below Microsoft's trading average over the last few years.”
Ackman added that Microsoft’s multiple does not reflect the value of its 27% stake in OpenAI (OPAI.PVT), which he said would be approximately $200 billion, or 7% of Microsoft’s market capitalization.Bill Ackman, founder and CEO of Pershing Square Inc., speaks during an interview during his company’s IPO on the floor of the New York Stock Exchange (NYSE), in New York City, U.S., April 29, 2026. REUTERS/Brendan McDermid·Reuters / REUTERS
“We believe Microsoft's recent share price decline has been principally driven by investor concerns around two key issues: i) the competitive positioning of M365 against increasingly capable AI lab offerings (notably Anthropic's Claude Cowork), and ii) the durability of Azure's growth, especially in light of Microsoft's evolving relationship with OpenAI,” Ackman continued.
“In our view, investors underestimate the resilience of the M365 franchise given its deeply embedded role across enterprises and highly attractive price-value proposition. Unlike point software solutions, which may be vulnerable to disintermediation by better-performing AI alternatives, M365 is tightly integrated into the daily workflow of nearly every large enterprise and is supported by Microsoft's identity, security, compliance, and data governance infrastructure, which would be nearly impossible to replicate. “
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Microsoft odds and ends: Microsoft’s stock has dropped 17% this year versus a 10% gain for the S&P 500 (^GSPC), as its third quarter results underwhelmed and worries about artificial intelligence investment surfaced.
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Microsoft said on its earnings call that it will spend $190 billion in capital expenditures for calendar year 2026 — up 61% from 2025. Consensus estimates were for $154.6 billion at the time, meaning Microsoft blew past Wall Street's estimate by roughly $35 billion.
But with that “bad” news out of the way, Evercore ISI chief technical analyst Rich Ross wrote in a recent note that Microsoft has one of the "best acting charts" in the tech space right now, noting that the stock has reclaimed its 50-day moving average with "authority."
He added that Microsoft can be "owned both fundamentally and technically," given the recent pullback to a long-term support level that has held since the European financial crisis.
Bottom line: Microsoft stock hasn't gotten a lot of love this year, clearly. But with the technical setup improving and concerns about the pace of Azure growth and capital expenditure plans well known, a positive shift in sentiment could emerge.
The Ackman purchase is a big vote of confidence in Microsoft by someone who has had success in investing in large-cap tech names, such as Alphabet (GOOGL).
"The Street continues to underestimate the Azure growth story in our view with an AI driven shift about taking place in Redmond heading into the back half of the fiscal year, making Microsoft one of our favorite large cap tech names to own over the coming years,” Wedbush tech analyst Dan Ives said in a note.
Brian Sozzi is Yahoo Finance's Executive Editor and a member of Yahoo Finance's editorial leadership team. Follow Sozzi on X @BrianSozzi, Instagram, and LinkedIn. Tips on stories? Email brian.sozzi@yahoofinance.com.
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- Bill Ackman Says He Bought the Dip in Microsoft Stock
May 15, 2026
Billionaire hedge fund manager Bill Ackman said his firm has taken a new position in Microsoft backing the company to be an artificial-intelligence winner. Ackman, who runs investment management firm Pershing Square Inc., said he had started building the position in Microsoft in February after the software giant fell in the wake of its earnings. “In our 13F which we will file later today, we will disclose a new position in Microsoft, a company we have followed for many years now offered at a highly compelling valuation,” Ackman wrote on social-media platform X on Friday.
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