How a Legendary Investor Is Concentrating Over Half His $14.4B Fund Into Three Power Stocks

When major institutional investors make bold moves, the market pays attention. Bill Ackman’s investment thesis deserves scrutiny—and his current portfolio concentration reveals a sophisticated bet on value that’s worth understanding.

The Concentrated Portfolio Strategy

Pershing Square Capital Management operates differently from most hedge funds. Rather than spreading capital across dozens of positions, Ackman builds conviction-based holdings in perhaps a dozen publicly traded companies. This concentrated approach demands discipline: each position must clear a high bar for long-term potential.

What’s striking about the current moment is that just three holdings now represent more than 51% of Pershing Square’s publicly traded portfolio. For context, that’s a $7+ billion concentrated bet across three separate companies—a level of commitment that signals deep confidence in both the valuations and long-term trajectories.

Uber: The Network Effect Play (19.7% of Portfolio)

The ride-sharing giant entered Pershing Square’s portfolio at the beginning of 2025, with the fund acquiring 30.3 million shares before publicly announcing the position. By Q1, it had become the largest holding. Since the announcement, Uber stock has surged approximately 55%, reaching all-time highs.

The valuation story remains compelling despite the run-up. At under 23x forward EBITDA, the stock trades at an attractive multiple relative to management’s guidance for 30%+ EBITDA growth over the coming years.

Beyond the numbers, Ackman appears to see structural advantages. Gross bookings climbed 14% in the most recent quarter, while EBITDA expanded 35%—demonstrating improving operating leverage. Free cash flow grew 66%, with the business converting more than 100% of EBITDA to free cash.

The autonomous vehicle opportunity exemplifies why traditional industry threats might become strategic assets. With 170 million monthly active users, Uber possesses the largest consumer base in ride services globally. Waymo and other self-driving platforms would find significant value accessing this network, making Uber a potential infrastructure play rather than a disrupted business.

Brookfield: The Institutional Capital Compounding Machine (18.4%)

Over four quarters, Ackman has methodically built this position in the Canadian alternative asset manager. Brookfield operates a diversified ecosystem spanning asset management, real estate, renewable energy infrastructure, and insurance operations—each generating cash flows that feed back into the investment machine.

This structure mirrors the Berkshire Hathaway playbook that Ackman has openly admired: using operating cash flows and insurance float to acquire additional profitable assets while returning cash via buybacks and dividends.

The growth trajectory speaks clearly. Distributable earnings per share have expanded at 19% annually over five years, with management targeting $6.33 per share by 2029—representing a 16% compound annual growth rate. In Q1 alone, earnings jumped 30%.

The market has yet to fully price this expansion. At 19x trailing earnings, Brookfield trades below peer multiples despite demonstrating superior growth visibility. The combination of predictable recurring revenues from asset management and insurance float, coupled with opportunistic investment returns, creates a resilient earnings stream.

Howard Hughes: The Restructured Real Estate Platform (13.3%)

Howard Hughes represents perhaps the most ambitious play. In May, Ackman increased his stake through a $900 million investment, securing a 46.9% economic interest and 40% voting control. More significantly, he reassumed the executive chairman role with a mandate to transform the company into a diversified holding company framework.

The fundamental asset value appears substantially disconnected from market valuation. Management’s net asset value calculation pegged the underlying real estate—master planned communities, condominiums, and operating assets minus corporate debt—at approximately $5.8 billion per share as of year-end. The company’s entire market capitalization sits around $4 billion.

The operational foundation is solid. Howard Hughes generates strong cash flows through land sales to homebuilders and rental income from commercial and multifamily properties. Since the company controls entire communities, it can match supply to demand precisely, optimizing returns on capital deployment.

The restructuring fees—$3.75 million quarterly plus 0.375% of value increases above inflation—do represent costs. However, this arrangement democratizes access to Ackman’s deal-making capability, allowing retail investors to participate in future acquisitions and restructuring opportunities alongside the institutional fund.

The Underlying Investment Thesis

What connects these three holdings is a shared characteristic: each trades below intrinsic value while offering multiple paths to value creation. Uber benefits from network effects and operational leverage. Brookfield compounds through disciplined capital deployment. Howard Hughes unlocks dormant real estate value through repositioning.

For investors examining concentrated portfolio bets, the positioning across these three names illustrates how conviction-based investing operates at scale. Each position arrived after rigorous analysis, represents billions in capital, and reflects a multi-year investment horizon rather than tactical positioning.