Legendary investor who made an estimated $100 million on 1987 crash says investors could see 'negative 10-year returns'
Key takeaways
- In October 1987, while the rest of Wall Street investors were losing their fortunes, Paul Tudor Jones was collecting one.
- Nearly four decades later, Jones is looking at today's stock market and he's uncomfortable.
- Thanks to Jeff Bezos, you can now become a landlord for as little as $100 — and no, you don't have to deal with tenants or fix freezers.
Legendary investor who made an estimated $100 million on 1987 crash says investors could see 'negative 10-year returns' Aditi Ganguly Sun, May 10, 2026 at 9:00 PM GMT+7 10 min read ^GSPC Moneywise and Yahoo Finance LLC may earn commission or revenue through links in the content below.
In October 1987, while the rest of Wall Street investors were losing their fortunes, Paul Tudor Jones was collecting one. He had spent months studying the parallels between the 1987 and 1929 crash (1), positioned his fund against the market, and when the Dow dropped 22% in a single day (2) — still the largest single-session percentage decline in history — his short bets made him an estimated $100 million.
Nearly four decades later, Jones is looking at today's stock market and he's uncomfortable. His warning: buying the S&P 500 at current valuations could lead to negative 10-year returns.