Bill Ackman’s Pershing Square Gains 25% in 2025: Two Bets Powering the Surge

Billionaire hedge fund manager Bill Ackman is once again proving why his investment instincts command attention on Wall Street. His flagship vehicle, Pershing Square Holdings, has surged 25% year-to-date in 2025, a performance that has outpaced both the S&P 500 and many rival hedge funds.

According to recent investor letters and regulatory filings, two strategic bets stand out as the primary drivers of these gains: a renewed position in Alphabet (Google’s parent company) and an aggressive move into U.S. housing-related financials.

Alphabet: Riding the AI and Ad Recovery Wave

Ackman’s bullish bet on Alphabet has turned into one of his most lucrative plays this year.

• Advertising Rebound: After a sluggish 2023–2024 period, digital advertising has rebounded sharply in 2025, with Alphabet reporting record-breaking ad revenues in the first half of the year.

• AI Expansion: Alphabet’s rollout of generative AI products across Google Search and YouTube has significantly boosted engagement metrics, driving up both subscription and ad-based revenue streams.

• Valuation Play: Ackman reportedly saw Alphabet as undervalued relative to its cash flow generation, adding heavily to his position in late 2024.

One Pershing Square insider noted,

“Ackman believed Wall Street was underestimating Alphabet’s ability to monetize AI. His conviction was clear, and so far, it’s paid off.”

U.S. Housing and Mortgage Finance: A Contrarian Win

Ackman also moved aggressively into housing-related financial firms, a contrarian bet at a time when high interest rates had rattled mortgage markets.

• Mortgage Servicers: Pershing Square took sizable stakes in mortgage servicing companies, anticipating that stability in interest rates would boost refinancing activity and servicing revenues.

• Homebuilders: Ackman also backed select U.S. homebuilders that benefitted from limited housing supply and strong demand, particularly in Sun Belt states.

• Policy Tailwinds: With the Federal Reserve signaling potential rate cuts in late 2025, the sector has rallied, rewarding Ackman’s timing.

Economist Laura Chen from Columbia Business School explained,

“While many funds were reducing exposure to housing, Ackman leaned in. He understood the supply-demand imbalance was still favoring long-term growth.”

Pershing Square’s Broader Strategy

Pershing Square has historically taken concentrated positions in a handful of large-cap companies, betting big when Ackman has conviction. This approach often results in volatile returns but can deliver outsized gains during periods of correct positioning.

In addition to Alphabet and housing-related financials, Pershing maintains stakes in Chipotle, Restaurant Brands International, and Hilton Worldwide. While these holdings have performed steadily, they were not the primary contributors to this year’s surge.

How Ackman’s 2025 Performance Stacks Up

• Pershing Square Holdings: +25% year-to-date

• S&P 500: +12% year-to-date

• Average Hedge Fund (per HFR index): +6% year-to-date

This outperformance not only enhances Ackman’s reputation but also strengthens investor confidence in Pershing Square as one of the few actively managed funds consistently beating the market.

Looking Ahead: Risks and Opportunities

While Ackman’s 2025 gains are remarkable, analysts caution that concentrated bets can quickly reverse. Alphabet faces rising competition from Microsoft and OpenAI in AI search products, while the U.S. housing sector remains vulnerable to unexpected interest rate hikes or economic slowdowns.

Still, Ackman remains optimistic. In his most recent investor letter, he argued that Pershing’s positions are aligned with long-term secular growth trends, particularly in AI-driven technology and structural U.S. housing demand.

For more insights into Pershing Square’s holdings, investors can review Pershing’s official updates via the London Stock Exchange filings or explore hedge fund performance trends at Institutional Investor.