Analyzing Pershing Square's Major Portfolio Plays: What's Behind Ackman's Strategic Bets Heading Into 2026

Three High-Conviction Investments Reshaping the Hedge Fund’s Direction

Throughout 2025, Bill Ackman’s Pershing Square has concentrated significant capital into three marquee positions that reveal the fund’s market thesis for the year ahead. These investments—spanning mobility services, athletic retail, and cloud infrastructure—represent roughly $4 billion in deployed capital and showcase Ackman’s confidence in long-term value creation despite near-term volatility.

The Cloud Computing Play: Amazon’s Underappreciated Competitive Moat

When Ackman initiated a $1 billion position in Amazon in April, critics questioned the timing. Yet the investment reflects a sophisticated thesis about enterprise digital transformation. Amazon Web Services alone demonstrated 20% growth in Q3, yet the broader opportunity remains nascent—with only 20% of enterprise computing currently cloud-based, the addressable market could double as legacy systems migrate.

On the retail side, Amazon’s logistics optimization is yielding tangible results. The company restructured its fulfillment network into regional hubs, simultaneously reducing per-unit shipping costs while accelerating same-day delivery volumes. This operational efficiency is flowing directly to margin expansion at a time when wholesale pricing pressures typically compress returns.

At 29 times forward earnings, Amazon commands a premium to Ackman’s April entry point of 25x. Yet for a business generating sustainable growth across two distinct $100+ billion revenue streams, the valuation remains rational. The stock’s 2025 performance tracking the S&P 500 suggests the market hasn’t fully priced in the profitability inflection gaining momentum.

The Demand Aggregator Thesis: Uber’s Role in the Autonomous Vehicle Ecosystem

Ackman’s February disclosure of a 30.3 million share stake in Uber—roughly $2 billion deployed—has proven prescient, with shares appreciating approximately 50% year-to-date. But the investment case transcends near-term momentum.

The core insight: autonomous vehicle companies, particularly well-capitalized operators like Waymo, need reliable demand networks to prove unit economics at scale. Uber’s monthly active users have grown 17% in consecutive quarters, while trip frequency metrics reveal 22% gains in bookings and 21% increases in gross billings. These demand-side metrics matter because they demonstrate network depth that even market-leading autonomous operators cannot easily replicate.

Waymo has signed dozens of partnership arrangements to access Uber’s platform, with new agreements continuing monthly. This dynamic transforms Uber from a threatened incumbent into an indispensable infrastructure layer. Ackman projects this positioning can drive 30% earnings-per-share growth over the foreseeable future. With Uber as the hedge fund’s largest liquid position, conviction remains high despite the stock’s 25x forward multiple already reflecting significant optimism.

The Optionality Play: Nike’s Turnaround Potential Under New Leadership

The Nike position represents a higher-conviction-per-dollar risk-reward profile than the outright equity stakes. Rather than hold 18 million shares accumulated in 2024, Ackman’s team restructured the $1.4 billion stake into deep in-the-money call options at the year’s outset, positioning the portfolio to capture double the stock’s upside should the turnaround succeed.

That thesis is being tested. Nike shares have declined 13% in 2025 as CEO Elliott Hill executes a “Win Now” strategy emphasizing wholesale channel expansion and brand-led premium positioning. Recent results show 1% revenue growth driven by wholesale momentum, though direct-to-consumer channels face headwinds as the company purges clearance inventory.

The strategic reset makes sense: higher wholesale volumes support premium pricing, while eliminating discount-driven direct sales reduces operating overhead. Brand equity accumulated over decades creates competitive defensibility that retail partners cannot easily displace. Tariff headwinds estimated at $1 billion annually represent manageable friction given supply chain optimization opportunities.

The call option structure creates asymmetric risk: the low break-even point limits downside, while meaningful upside accrues if Hill’s transformation gains momentum before option expiration. Time remains a factor—unlike equity holders enjoying perpetual optionality, Ackman’s team operates within contractual boundaries. Yet if the turnaround inflects positively, the returns could dwarf traditional equity appreciation.

Strategic Positioning Entering 2026

Pershing Square’s 2025 portfolio construction reveals an investor increasingly focused on structural business improvements and market dislocations rather than macro timing. The Uber and Amazon positions benefit from secular tailwinds in autonomous vehicles and cloud adoption, respectively. Nike represents a discretionary bet on operational excellence and brand resilience.

Collectively, these three positions—totaling roughly $4 billion in capital deployment—will likely remain core holdings through 2026, with their performance serving as key indicators of whether Ackman’s thesis about long-term value creation in mature technology and services businesses remains intact.