Bill Ackman's 2025 Portfolio Moves: Three Bold Bets That Define His Investment Thesis

The past year has been a telling one for legendary investor Bill Ackman and his Pershing Square hedge fund. While running one of Wall Street’s most closely watched portfolios, Ackman made several decisive moves that showcase his conviction in specific market opportunities. As 2026 unfolds, three of his positions stand out as the clearest signals of where he believes significant returns lie.

Amazon: Playing the Long Game on Cloud and Retail Dominance

Among the most intriguing of Bill Ackman’s recent moves was his $1 billion acquisition of 5.8 million Amazon shares during April’s market volatility. The timing coincided with Trump’s tariff announcement, presenting what Ackman viewed as a tactical entry point. Since then, Amazon has merely tracked the broader S&P 500, yet Ackman’s conviction remains unshaken.

His thesis rests on two pillars. First, Amazon Web Services continues to capture the artificial intelligence boom, with demand so robust the company struggles to build server capacity fast enough despite investing tens of billions quarterly. Cloud represents a massive long-term runway: today’s enterprise computing sits at only 20% cloud penetration, a figure expected to expand dramatically. AWS demonstrated 20% growth in Q3 alone, with management signaling this pace can persist.

Second, the retail juggernaut is experiencing margin expansion through logistics optimization. After overhauling its fulfillment network into regional systems, Amazon has simultaneously reduced shipping costs while expanding one-day delivery capabilities. Prime subscription revenue and volume growth continue supporting financial momentum. At a 25x forward earnings multiple when purchased, Amazon’s valuation has since ticked up to approximately 29x 2026 expectations—still reasonable for a company posting exceptional earnings growth across both business segments.

Uber: The Mobility Aggregator Play

In February, Bill Ackman publicly disclosed Pershing Square’s substantial 30.3 million share purchase in Uber Technologies, representing roughly $2 billion committed. The position has delivered handsomely, with shares appreciating 50% year-to-date.

Ackman’s investment thesis centered on market undervaluation, particularly concerning investor fears around autonomous vehicles. His contrarian view: Uber’s network effects as a demand aggregator position it as essential infrastructure for autonomous vehicle companies, not a competitive threat. This prediction has proven prescient, with Waymo and other AV developers actively utilizing Uber’s platform for testing and deployment across numerous cities.

Operationally, the platform continues strengthening its metrics. Monthly active consumer growth accelerated consecutively over the last two quarters, reaching 17% growth in Q3. Usage intensity is equally impressive: total trips booked surged 22%, while gross bookings climbed 21%. These dynamics support Ackman’s expectation of roughly 30% near-term earnings-per-share expansion. Trading at 25x forward earnings, Ackman evidently views upside remaining, keeping Uber as his hedge fund’s largest publicly traded equity holding as of Q3.

Nike: Patience Required on the Turnaround

Ackman’s Nike strategy diverged from a traditional equity approach. After building an 18 million share position in 2024, he liquidated the stock at year-end and rotated into deep in-the-money call options instead. The rationale: options could deliver double the stock’s returns if turnaround efforts succeed, while his initial $1.4 billion stake provided substantial conviction.

Performance has lagged so far, with Nike shares down 13% year-to-date despite management traction under new CEO Elliott Hill’s “Win Now” strategy. The approach emphasizes wholesale partnerships, innovation, and brand leverage—Nike’s traditional competitive moats. Q3 revenue expanded 1%, supported by wholesale channel strength, though management acknowledges direct-to-consumer sales will weaken as clearance inventory exits the system. Offsetting this, margins should expand absent discount pressure.

The tariff environment presents near-term headwinds, estimated at $1 billion annually, though management is executing mitigation tactics. Bill Ackman appears unmoved by current stock weakness; holding multi-year call options with minimal break-even prices minimizes downside while preserving explosive upside if turnaround momentum crystallizes before expiration. The position’s optionality and low loss probability keep Ackman engaged heading into 2026.

The Conviction Behind the Bets

These three positions collectively represent Bill Ackman’s clearest market convictions. Amazon targets structural cloud growth and retail efficiency, Uber exploits autonomous vehicle network effects, while Nike hinges on brand-driven turnaround execution. Each reflects his documented preference for concentrated, multi-year holdings where patient capital can capitalize on evolving market narratives.