What's Driving Ackman's $4 Billion Portfolio Push in 2025? Three Stocks Reveal His Investment Thesis

The Big Picture: Pershing Square’s Concentrated Bets

Hedge fund manager Bill Ackman ran one of the industry’s most closely watched investment portfolios through Pershing Square Holdings in 2025. Rather than spreading capital across dozens of positions, he concentrated on a small number of high-conviction bets. Three major investments—valued at roughly $4 billion combined—demonstrate where he sees the most compelling opportunities heading into 2026. All three bets share a common thread: strong underlying business fundamentals combined with what Ackman believes is market undervaluation.

The Mobility Play: Why Ackman Sees Uber as Indispensable

Among Pershing Square’s 2025 moves, the Uber Technologies investment stands out for its early payoff. In February, Ackman disclosed a $2 billion stake consisting of 30.3 million shares. His thesis centered on ridesharing’s essential role in the emerging autonomous vehicle ecosystem.

The numbers have vindicated his timing. Uber stock surged 50% year-to-date, significantly outpacing broader market indices. More importantly, the company’s operational metrics tell a compelling story. Monthly active users accelerated during the last two quarters, climbing 17% in Q3. Users aren’t just downloading the app—they’re actively using it, with total trips booked up 22% and gross bookings rising 21% year-over-year.

Ackman’s longer-term conviction rests on Uber’s market position. As autonomous vehicles proliferate, smaller AV companies will need distribution channels. Industry leader Waymo has already struck dozens of partnerships via Uber’s platform and continues adding new agreements monthly. This dynamic suggests Uber will become an indispensable intermediary rather than a direct competitor.

The valuation tells an interesting story too. At 25 times forward earnings, Ackman believes the market hasn’t fully priced in his projected 30% earnings-per-share growth trajectory. He’s backing this conviction with capital—Uber remained Pershing Square’s largest equity position at the end of Q3.

The Athletic Brand Restructuring: Nike’s High-Risk Options Strategy

Ackman’s Nike position illustrates a different risk-reward calculation. After building an 18+ million share stake in 2024, he executed a strategic pivot at the start of 2025: selling the shares and reinvesting the $1.4 billion in deep in-the-money call options. This approach could double his returns if Nike’s turnaround succeeds—but options are time-limited tools.

Year-to-date, Nike shares declined 13%, testing Ackman’s patience and conviction. However, new CEO Elliott Hill’s “Win Now” strategy is showing early traction. The approach emphasizes wholesale partnerships, brand leverage, and margin expansion. Q3 results showed revenue growth of 1%, driven by wholesale channel strength, while management guides toward continued wholesale improvements throughout the year.

The margin story could prove decisive. As Nike phases out clearance items from direct channels, it’s reducing overhead while protecting pricing power. The company’s brand equity—built through decades of athlete partnerships and innovation—remains a significant competitive moat. Even in a tariff-heavy environment where Nike faces $1 billion in annual headwinds, the brand positioning should cushion against margin compression.

Ackman appears to have maintained his options position. With equity markets generally higher, his option break-even points remain favorably positioned. However, the clock matters here: options expire, but patience with a stock turnaround is indefinite. If Nike’s transformation accelerates before Ackman’s contracts expire, the payoff could be substantial.

The Infrastructure Bet: Amazon’s Dual-Engine Growth Model

The third major 2025 investment represents opportunistic capital deployment. Ackman purchased 5.8 million Amazon shares in April for approximately $1 billion, taking advantage of post-tariff announcement weakness.

Since then, Amazon stock has essentially tracked the S&P 500—neither impressive nor disappointing. Yet Ackman’s thesis extends well beyond near-term price action. His investment thesis rests on two distinct, world-class businesses operating within Amazon’s corporate structure.

In cloud computing, Amazon Web Services is experiencing structural tailwinds. AI adoption is driving demand acceleration, but that’s just one layer. Only 20% of enterprise computing currently resides in the cloud. As legacy systems gradually migrate, this ratio will likely invert over the coming decade. AWS grew 20% in Q3, and management indicated this pace could persist for years. Meanwhile, Amazon continues investing tens of billions quarterly into data center infrastructure and server capacity—spending that reflects confidence in multiyear growth trajectories.

The retail business is equally compelling. Amazon recently reorganized its U.S. fulfillment network into regional systems, dramatically reducing shipping costs while expanding same-day and next-day delivery capabilities. This logistics optimization is translating into margin expansion without sacrificing customer experience. Prime subscription revenue provides another lever, supported by the company’s distribution advantages.

Ackman’s April entry price was 25 times forward earnings—reasonable for the capital intensity and growth profile. Amazon now trades near 29 times 2026 earnings expectations. While that represents a modest premium to his original purchase price, it remains fair for a company generating exceptional earnings growth across two massive addressable markets. His position is likely to remain intact heading into 2026.

The Broader Thesis: When Does Conviction Pay?

These three positions reveal Ackman’s investment discipline. He concentrates capital where he identifies structural advantages, business model resilience, and market mispricing. Uber has already validated his thesis with strong returns. Nike and Amazon remain works-in-progress, requiring patience and conviction—hallmarks of his long-term approach.

Heading into 2026, all three positions suggest Ackman sees value that the broader market may not yet fully appreciate. Whether that conviction proves prescient will depend on corporate execution and market sentiment over the coming quarters.