Billionaire Bill Ackman’s hedge fund holds $1.3b Amazon stake

Pershing Square Capital Management held nearly US$1.3 billion in Amazon shares at the end of June, according to a recent regulatory filing.

The hedge fund, led by Bill Ackman, first mentioned its new Amazon stake during an analyst call in May.

Pershing disclosed a stake of over 5.8 million Amazon shares after the stock fell more than 30% earlier this year amid concerns about generative AI and US tariffs.

Amazon’s share price has risen 5.3% year-to-date, as of the market close on August 14, 2025.

🔗 Source: Bloomberg

🧠 Food for thought

1️⃣ Contrarian investing faces headwinds in passive-dominated markets

Pershing Square’s Amazon investment illustrates how even sophisticated hedge funds are adapting their strategies amid changing market dynamics.

The firm’s 10.2% net gain lagged the S&P 500’s 25% return, with Ackman noting that passive funds now account for over 54% of mutual fund and ETF assets1.

This passive dominance creates challenges for active managers like Pershing, which traditionally focuses on concentrated portfolios of high-quality companies through deep research and activist engagement2.

By building positions in major index constituents like Amazon and Alphabet, Pershing may be acknowledging that index inclusion has become increasingly important for investment success.

The timing of their Amazon entry—after a 30% decline due to AI and tariff concerns—reflects classic contrarian positioning, but their broader tech expansion suggests recognition that fighting against passive flows requires different tactics than in previous decades.

2️⃣ AI investment divergence creates opportunity for patient capital

The disconnect between AI hype and current market realities may have created the opening Pershing saw in Amazon’s depressed valuation.

While generative AI is projected to reach $1.8 trillion in market size by 2030 with a 37% compound annual growth rate, job postings have declined 25% since ChatGPT’s launch even as the S&P 500 gained 53%3 4.

This suggests that while investors are pricing in AI’s long-term potential, the immediate economic disruption is creating near-term uncertainty that benefits contrarian investors.