TradingKey - With just 11 stocks and $11.9 billion in equity assets, Bill Ackman’s Pershing Square portfolio remains a case study in concentrated, high-conviction investing. While 2025 has introduced volatility and competitive headwinds, Ackman’s core bets reflect a deliberate attempt to balance activist value with long-term structural growth.

Pershing Square, on March 31, 2025, has only 11 stocks in its portfolio worth $11.93 billion. Turnover in the fund reached an annual high of 22% during Q1, indicating strategic positioning rather than mere holding. Ackman's signature is still intact: a compact, concentrated portfolio in which every position earns its place through conviction and activist possibilities.

New additions are Uber Technologies (UBER), now the fund's largest holding at 18.5% of assets. Large stakes are also held in Brookfield Corp (BN) at 18.0%, Restaurant Brands International (QSR) at 12.9%, Howard Hughes Holdings (HHH) at 11.7%, and Chipotle Mexican Grill (CMG) at 9.1%. This blend is an indication of a combination of secular compounding and underappreciated plays with optionality, most notably in real estate (HHH), infrastructure (BN), and consumer discretionary (CMG, QSR).

Uber: A Thesis in Disguise

The most prominent Q1 headline is Ackman's gigantic new bet on Uber (UBER). Well over 30 million shares worth $2.2 billion, the holding is not merely a trade but a multi-year thesis on platform dominance, margin expansion, and optionality in Uber Eats, freight, and self-driving logistics. With UBER shares almost 16% higher than where shares bought by Ackman stood, returns thus far are confirming the bet. It is, however, still a wager on Uber's success in transitioning from cash burn to return of capital, a journey still in progress.

Brookfield: Where Infrastructure Converges

Brookfield Corp (BN), his second-largest holding, is greater than a mere traditional asset manager. His holding rose 17.5% in Q1, reflecting increasing conviction. Brookfield's combination of real assets, credit platforms, and private equity provides scale and protection against losses, particularly in an environment of high interest rates. Ackman seems to be positioning Pershing Square to capitalize on the “financialization of infrastructure” in which real assets such as renewables, data centers, and toll roads are financialized through capital-light operating models. Brookfield provides leverage to this trend.

Alphabet, Hilton, and the Art of the Trim

Not all the holdings were enlarged. Those held in Alphabet (GOOG) were cut by 16.2%, Chipotle (CMG) by 12.6%, and Hilton (HLT) by 44.8%. These sell-offs most likely constitute a combination of profit-taking and rebalancing, Alphabet specifically having struggled with AI monetization relative to the likes of Microsoft and Meta. Hilton, a long-standing Pershing stalwart, might be running out of room on the upside after decades of line-item expense optimization. Post-pandemic normalization in the hospitality industry appears to be plateauing, and the 45% drop assumed by Ackman implies a strategic reallocation of capital towards faster-growing sectors.

Transportation Pitch: Hertz and Canadian Pacific

Ackman still holds a significant 8.7% stake in Canadian Pacific Kansas City (CP), further substantiating his preference for logistics and infrastructure. Rail is a quiet compounding machine, but one that is supported by operational leverage and macro tailwinds such as reshoring and supply chain restructurings. Ackman also bought Hertz (HTZ), expanding his holding by 18% after he first got in towards the end of 2024. It is still a small holding, but it is a bet on turnaround themes, if Hertz is able to stabilize the margins in a capital-intensive, transitioning-to-EV rental environment.

Sector Focus: Industrial and Consumer-Oriented

Pershing Square's industrial exposure through CP and Hertz makes up almost 9.2% of the portfolio. Transportation is dominant, with small segments of business services. On the opposite side, Ackman's exposure is heavily biased in consumer-facing names such as CMG, QSR, and UBER. This sector weighting is consistent with Ackman's activist DNA: he likes businesses with pricing power, brand value, and operating levers. Of particular note is the avoidance of energy, healthcare, and small caps, further reflecting Ackman's "quality-at-scale" orientation.

Historical Performance: Feast and Famine

Ackman's long-term record is characterized by boom-bust cycles. His fund earned 56.6% in 2020 and 44.1% in 2019 but underperformed the S&P 500 during both 2021 and 2023. In 2024, Pershing returned a modest 8.2%, well behind the S&P's 23.3%. The underperformance is a result of a lack of exposure to mega-cap tech and AI names. While most of his peers chased Nvidia and Microsoft, Ackman remained in traditional sectors, opting for value plays with catalysts versus growth themes.

2025 Year-To-date: A Bumpy Ride

From April to May 2025, hypothetical Pershing Square portfolio gains have reflected a rollercoaster ride of volatility. At one time lagging behind the S&P by over 15%, the portfolio caught up on some ground, trailing by a narrower percentage. Notably, the rebound followed after Uber and Brookfield reported strong results, affirming longer-term picks by Ackman. Nevertheless, mid-portfolio reduction in Alphabet and Hilton implies ongoing repositioning while market leadership rotates.

Strategic Vision: Conviction

Ackman's 2025 positioning is a reflection of a distinct philosophy: focused, event-driven, and brand-driven. It's not riding the AI hype cycle or diversifying based on appearances. It's still a high-stakes, high-conviction business, where every name is a purposeful bet, not a passive holding. 

With turnover climbing and cash most probably being redeployed, anticipate further evolution of his central themes: platform businesses with monetization opportunity, underappreciated real assets, and consumer names with latent pricing power. The flip side? Inadequate exposure to secular tech trends may detract from performance in AI-fueled bull cycles. The silver lining? When catalysts arrive, be assured that Ackman comes in swinging.

Conclusion: A Focused Contrarian in an Era of Crowded Trades

In a breadth-driven market, Ackman's is anything but a broad portfolio. It holds a mere 11 names, a reflection both of conviction and concentration risk. Uber's rise to a top holding is aggressive, and Brookfield's growth orientation brings long-duration leverage. Alphabet and Hilton trims reflect discipline in the face of shifting cycles. 

Pershing Square is not the solution for allocators looking for diversification but perhaps one of the most intriguing portfolios to observe in 2025 for those in pursuit of alpha through focus, catalysts, and asymmetric upside. Typically with Ackman, the message is in the magnitude. When he wagers, he wagers heavily, and each position comes with a narrative.

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