Inside Bill Ackman's $10 Billion Investment Portfolio: A Strategic Repositioning

Billionaire investor Bill Ackman continues to captivate Wall Street with his concentrated investment approach. As head of Pershing Square Capital Management, Ackman oversees more than $10 billion in assets and has built a reputation as a fundamental value investor who doesn’t believe in diversification for its own sake. His portfolio typically contains just eight to 12 holdings, with each position representing a significant conviction. In the most recent quarter, this focused strategy revealed significant shifts that offer valuable insights into how elite investors adapt to changing market conditions.

The Ackman Investment Philosophy: Why Concentration Beats Diversification

Bill Ackman’s portfolio strategy stands in stark contrast to traditional indexing approaches. Rather than spreading capital across dozens or hundreds of companies, Pershing Square places substantial, long-term bets on what Ackman considers best-in-class businesses with durable competitive advantages. The hedge fund explicitly targets high-quality, large-cap North American companies with limited downside and predictable cash flows — characteristics that translate into measurable results. Over the past five years, Pershing Square has generated a 31% annualized return, roughly double the S&P 500’s performance.

This outperformance validates Ackman’s thesis that deeper research and conviction-based investing can systematically beat the market. Unlike activists who constantly churn their portfolios, Ackman typically holds positions for years, allowing compounding and thesis development to work in his favor. However, the recent quarter showcased that even long-term conviction investors must remain flexible when valuations become stretched or fundamental dynamics shift.

Core Holdings Remain Strong Despite Portfolio Adjustments

The portfolio’s foundation continues to rest on several marquee positions that have delivered exceptional returns. Hilton Worldwide Holdings, representing 19% of the portfolio with nearly 9 million shares worth approximately $1.9 billion, remains Ackman’s oldest and most profitable bet. Since initiating the position in late 2018 — and notably accumulating during the pandemic when travel was severely disrupted — this holding has validated Ackman’s recovery thesis. In the first half of 2024, Hilton demonstrated revenue growth of 11% with EPS jumping 17%, evidence of the company’s strong operational leverage and disciplined capital management.

Restaurant Brands International, comprising 16% of assets, similarly showcases Ackman’s patience with portfolio construction. His initial investment in 2012 — when the company was privately held — preceded its eventual IPO and has compounded significantly. The portfolio company, which operates Burger King, Tim Hortons, Popeyes, and Firehouse Subs, continues to benefit from its franchised royalty model. With first-half 2024 revenue and earnings both climbing 13%, the position demonstrates the recurring revenue streams Ackman seeks.

Howard Hughes Holdings, maintained at 13% of the portfolio, represents perhaps the most complex and patient capital deployment. Ackman’s conviction in the master-planned communities business model reflects his willingness to invest in specialized real estate strategies that generate returns over decades rather than quarters. The company’s record earnings before taxes and operating income in the period validate this patient approach.

Canadian Pacific Kansas City rounds out the portfolio’s established foundation at 12% of assets. Ackman’s 2021 repositioning in this North American railroad — strengthened by the transformative acquisition of Kansas City Southern — demonstrates his attraction to oligopolistic industries with durable competitive moats. The company’s 27% adjusted EPS growth in the period, coupled with 14% revenue expansion, underscores the quality of the business.

Major Shifts: Why Ackman Trimmed Chipotle and Alphabet

The quarter revealed two significant portfolio adjustments that warrant careful analysis. Chipotle Mexican Grill had represented Pershing’s largest single holding heading into the period but experienced meaningful trimming. Ackman reduced his position by 23%, selling more than 8 million shares despite the company’s exceptional operational performance — revenue climbed 18% with EPS jumping 32% on same-store sales growth of 11%.

The decision to sell strength is characteristic of a disciplined value investor. At the end of the quarter, Chipotle traded at 58 times sales, a valuation multiple that Ackman apparently deemed stretched relative to long-term earning power. The departure of CEO Brian Niccol to Starbucks presented an additional consideration, though Ackman publicly expressed confidence that the management team Niccol built would sustain momentum. This reflects a calculated judgment that while the company remains high-quality, price had moved ahead of value.

Similarly, Ackman reduced his Alphabet Class C position by 20%, selling 1.8 million shares despite the company’s robust 15% revenue growth and 31% EPS expansion in the quarter. The company’s substantial artificial intelligence investments and 2 billion-user ecosystem continue to position it for long-term growth. However, the antitrust verdict declaring Google’s search monopoly illegal — while handed down post-sale — likely informed Ackman’s decision-making calculus regarding valuation. With Class C shares continuing to modestly outpace Class A shares, the reduction appears driven by pure valuation discipline rather than thesis deterioration.

New Bets on Brookfield and Nike Reflect Ackman’s Value Hunting

The quarter’s most intriguing development involved Ackman’s entry into two new positions that exemplify his current thinking about market opportunities. Brookfield Corp, the alternative asset and real estate investment manager, was added as a 3% position worth approximately $321 million. Rising interest rates have dampened sentiment on real asset managers, leaving the stock essentially flat over three years. Despite challenging conditions, Brookfield generated year-over-year distributable earnings growth of 11% with adjusted distributable earnings up 80%, suggesting the market has underpriced the business.

Nike, added at 2% of the portfolio representing roughly 3 million shares worth $239 million, represents the other notable new entry. After declining 50% over recent years amid inflationary headwinds, the company appears to satisfy Ackman’s dual criteria: a world-class franchise with proven competitive advantages and a valuation discount that reflects temporary challenges rather than permanent impairment. Trading at just 22 times trailing earnings despite flat fiscal 2024 revenue and 15% earnings growth, Nike fits the profile of a turnaround candidate in which Ackman clearly sees resiliency.

These new positions suggest Ackman is identifying opportunities in overlooked sectors — both positioned to benefit as interest rates moderate and growth concerns ease. The measured position sizing (3% and 2% respectively) indicates conviction tempered by prudence, a hallmark of the Pershing Square approach.

What This Portfolio Tells Us About Market Opportunities Ahead

Bill Ackman’s portfolio adjustments in mid-2024 convey multiple signals about the current investment landscape. The trimming of expensive growth names (Chipotle, Alphabet) while establishing positions in undervalued recovery stories (Nike, Brookfield) suggests a rebalancing toward value after a period of growth-driven leadership. His continued commitment to transportation (railroads), consumer spending (restaurant brands, hospitality), and real estate indicates comfort with North American economic durability despite macro headwinds.

The concentration in just nine holdings underscores that conviction-based investing — backed by rigorous analysis and willingness to sit through volatility — can outperform traditional approaches. Bill Ackman’s portfolio remains a master class in disciplined capital allocation: holding winners for years, trimming when valuations become stretched, and maintaining readiness to deploy capital when opportunity meets price. For investors studying this approach, the key lesson remains unchanged: quality combined with price discipline creates durable returns.