Ackman's 2025 Investment Playbook: Why He's Betting Big on Mobility, Retail, and Cloud

Bill Ackman runs Pershing Square Holdings, one of the world’s most closely watched hedge funds. While he’s also chairman of Howard Hughes Holdings after significantly expanding that stake, the real action happens in his concentrated portfolio of high-conviction plays. When Ackman makes a move, the market pays attention—especially when capital flows reveal his true conviction levels.

Three of his 2025 positions stand out as his biggest bets heading into 2026, each worth over $1 billion. Here’s what his positioning tells us about where he thinks the real value is.

Uber’s Dominance in the Autonomous Vehicle Ecosystem

The ride-sharing space looked crowded, but Ackman saw something others missed when he disclosed a $2 billion stake in Uber Technologies back in February. He deployed 30.3 million shares at a time when market sentiment was heavily weighted against the company’s long-term prospects.

The trade has worked spectacularly—shares are up 50% year to date. But the stock’s performance is just confirming what Ackman’s thesis already suggested: Uber’s real moat isn’t just being the largest mobility aggregator today; it’s becoming the indispensable distribution network for autonomous vehicle makers tomorrow.

Monthly active users are growing at accelerating rates, up 17% in Q3 alone. Users themselves are stickier, leading to a 22% jump in total trips booked and a 21% increase in gross bookings. Waymo, despite being a dominant player in self-driving technology, keeps signing new partnership deals with Uber every month to distribute its autonomous services.

Ackman’s calculus: As smaller AV companies lack the capital to build their own distribution networks, they’ll have no choice but to use Uber. Even the giants like Waymo see strategic value in it. This dynamic should drive Uber’s earnings per share growth to roughly 30% annually going forward. At 25 times forward earnings, Ackman’s numbers suggest room remains, which is why Uber stayed his largest equity position through Q3.

Nike’s Turnaround: Betting on Options, Not Stock

Nike tells a different story—one about conviction facing near-term headwinds. Ackman built an 18 million share position in 2024, then made a tactical shift at year-start: he sold the stock and rotated into deep in-the-money call options instead.

The logic? Options could deliver double the returns if the turnaround succeeds. His $1.4 billion position was structured for asymmetric payoff, not downside protection.

Nike shares have fallen 13% this year, testing the thesis. Yet CEO Elliott Hill’s “Win Now” strategy is showing early progress. Revenue grew 1% last quarter, driven entirely by wholesale channel expansion. While direct-to-consumer sales will decline as management clears inventory, profit margins should expand without the discount pressure.

The brand equity Nike has accumulated over decades won’t evaporate overnight. The company is still signing premier athletes and remains the category leader in performance footwear. Its wholesale partnerships give it access to undifferentiated retail channels where strong branding can command premium positioning and pricing power.

Tariff headwinds will cost the company roughly $1 billion annually until supply chain mitigation kicks in. That’s a real obstacle, but not insurmountable. Ackman hasn’t bailed on the position. With option contracts’ low break-even thresholds minimizing loss risk, the real question is whether Hill can execute the turnaround before expiration. The clock is ticking, but the payoff potential is substantial if transformation happens on schedule.

Amazon: The Underappreciated Two-Engine Business

The third major 2025 addition came in April when Ackman bought 5.8 million Amazon shares for around $1 billion during the post-Trump-tariff selloff. The stock has merely kept pace with the S&P 500 since then, but Ackman believes the long-term opportunity is being underpriced.

His thesis rests on Amazon’s two core engines: e-commerce and cloud infrastructure. In cloud computing, Amazon Web Services has become the category leader, and AI demand is now creating a supply crisis. Despite pouring tens of billions into data centers and servers quarterly, AWS still can’t build infrastructure fast enough to meet demand.

Critically, only 20% of enterprise computing currently lives in the cloud. That percentage should flip over time, meaning AWS’s long-term runway extends far beyond today’s AI boom. CEO Andy Jassy indicated the 20% year-over-year growth AWS posted in Q3 can persist for “a while” longer.

On the retail side, Amazon has achieved substantial operating margin expansion through logistics network optimization. After aggressively building fulfillment centers early in the decade, management completely restructured its U.S. operations into regional hubs. The result: faster one-day delivery, lower fulfillment costs, and accelerating revenue growth.

Prime subscription revenue provides sticky recurring income that most of Wall Street undervalues. Ackman bought at 25 times forward earnings in April. Today’s 29 times multiple is slightly higher, but reasonable for a company producing exceptional earnings growth across two massive markets. Expect him to hold through 2026.

The Common Thread

All three positions share a pattern: Ackman identified structural business advantages that the market either missed or temporarily repriced downward. Whether it’s Uber’s role in autonomous mobility distribution, Nike’s brand-to-margin leverage, or Amazon’s cloud-to-enterprise penetration opportunity, each reflects conviction in secular trends playing out over years, not quarters. That’s how Pershing Square builds wealth for the long term.