Bill Ackman's Three Major Portfolio Plays Heading Into 2026: Investment Thesis Breakdown

Key Highlights

• Bill Ackman’s Pershing Square deployed significant capital across three major equity positions in 2025
• Each investment carries distinct risk-reward profiles and turnaround timelines
• Portfolio positioning suggests sustained conviction despite mixed year-to-date performance
• Long-term holding strategy remains consistent with Ackman’s historical investment approach

The Largest Stake: Uber’s Platform Resilience

Bill Ackman made waves in February when Pershing Square disclosed its approximately $2 billion investment in Uber Technologies, acquiring 30.3 million shares at what the hedge fund believed represented substantial undervaluation.

The thesis has materialized impressively—shares have appreciated 50% year-to-date, driven by accelerating operational momentum. Monthly active users grew 17% in Q3, while trip volumes surged 22% and gross bookings climbed 21%, signaling user engagement intensification beyond mere platform adoption.

Ackman’s strategic insight focuses on Uber’s emerging role as essential infrastructure for autonomous vehicle deployment. Market-leading AV companies like Waymo have already struck dozens of partnership arrangements, with new deals emerging monthly. This positions Uber as the indispensable aggregator connecting self-driving vehicle operators to consumer demand networks—a competitive moat that strengthens as adoption accelerates.

The investment thesis projects roughly 30% earnings-per-share expansion on a forward basis. With shares trading at approximately 25x forward earnings, Ackman’s continued positioning as the hedge fund’s largest marketable equity stake reflects confidence that current valuations still leave room for appreciation.

The Options Gamble: Nike’s Turnaround Potential

Bill Ackman’s approach to Nike illustrates sophisticated position management. Having established an 18 million-share foundation during 2024, Pershing Square pivoted at year-start into deep in-the-money call option contracts structured to deliver double the returns of equivalent stock ownership if the turnaround succeeds.

This strategic maneuver transformed the $1.4 billion position into leveraged exposure. Year-to-date performance has lagged—Nike shares have declined 13%—yet management’s “Win Now” strategy under new CEO Elliott Hill exhibits tangible progress. Q3 wholesale revenues grew 1%, with management guidance suggesting continued channel expansion offset by planned direct-to-consumer contraction.

The margin expansion story hinges on eliminating clearance discounting while maintaining wholesale relationships. Nike’s enduring brand strength provides marketing leverage in undifferentiated retail channels, potentially enabling better returns with leaner cost structures. Current tariff headwinds ($1 billion annual impact) add urgency to supply chain optimization initiatives.

The options’ low break-even pricing shields against total loss while preserving substantial upside if Nike’s restructuring gains momentum before expiration dates arrive—a calculated risk reflecting Ackman’s conviction that turnaround catalysts remain intact.

The Infrastructure Play: Amazon’s Cloud and Logistics Edge

Bill Ackman’s third major 2025 deployment targeted Amazon, deploying approximately $1 billion for 5.8 million shares during April’s tariff-driven selloff. Year-to-date returns have tracked S&P 500 performance, yet the long-term thesis emphasizes structural competitive advantages across dual core businesses.

Amazon Web Services has experienced 20% growth in cloud computing revenue, constrained by insufficient capacity relative to AI-driven demand escalation. Management indicates this expansion trajectory can persist “for a while” as enterprises recognize that only 20% of computing currently operates in cloud environments—suggesting a massive addressable market expansion as migration accelerates.

Retail operations demonstrate operational excellence through logistics network optimization. After two years of aggressive fulfillment center buildout, Amazon restructured into regional distribution systems, reducing delivery costs while expanding same-day availability. This supports Prime subscription resilience and revenue growth without proportional cost inflation.

The entry valuation of 25x forward earnings proved advantageous—shares now command approximately 29x 2026 earnings expectations. This modest premium reflects legitimate confidence in dual-engine earnings growth, where both segments exhibit expanding margins and revenue acceleration.

Synthesis: Conviction Across Market Cycles

Bill Ackman’s positioning emphasizes sustained conviction despite uneven 2025 performance. The Uber investment validates market recognition of competitive positioning. Nike’s options structure transforms underperformance into optionality for meaningful upside. Amazon’s infrastructure dominance addresses secular cloud migration and logistics efficiency trends extending well beyond current cycles.

Each position reflects differentiated risk-reward calibration rather than homogeneous exposure—a hallmark of concentrated portfolio management where position sizing matches conviction levels and capital allocation remains disciplined heading into 2026.