greatest investors of all time

01

Jesse Livermore

He made $100 million shorting the 1929 crash, then lost it all twice more. Jesse Livermore walked into a New York coat-check room with a pistol in 1940. The note said he was a failure.

02

George Soros

On September 16, 1992 — 'Black Wednesday' — George Soros shorted $10 billion in British pounds and pocketed $1 billion before London's close. The Bank of England spent $27 billion defending sterling and lost.

03

Hetty Green

Worth $100 million in 1900, Hetty Green wore the same black dress until it rotted and allegedly refused a surgeon's fee for her son Ned's infected leg — he lost the limb. She ate cold oatmeal to avoid heating it.

04

Jay Gould

Jay Gould and partner James Fisk cornered the entire U.S. gold market in September 1869. On 'Black Friday' the price collapsed, ruining thousands — while Gould had already quietly sold at the peak.

05

Ivan Boesky

Ivan Boesky told a 1986 UC Berkeley commencement crowd 'greed is healthy' to warm applause. Fourteen months later he paid $100 million in fines and named his Wall Street sources. His speech inspired the Gordon Gekko line.

06

Long-Term Capital Management

Long-Term Capital Management had two Nobel laureates on its board and leverage of 25-to-1. When Russia defaulted in 1998 the fund lost $4.6 billion in four months, and the Federal Reserve had to organize a private bailout.

07

Renaissance Technologies

Jim Simons's Medallion Fund returned 66% annually from 1988 to 2018 — after 5% management and 44% performance fees. It is closed to all outside investors. Its math remains a trade secret.

08

Daniel Drew

Daniel Drew fed his cattle salt before driving them to market, then let them drink until bloated — inflating the weighed price. He applied the same trick to Erie Railroad stock certificates, flooding the market to crush rivals.

09

Paul Tudor Jones

Paul Tudor Jones filmed himself predicting the 1987 crash with eerie precision — charts, dates, the exact word 'collapse.' He then spent years suppressing the documentary, reportedly buying up every copy to prevent distribution.

10

Cornelius Vanderbilt

When New York's legislature sided against him in an 1867 rail dispute, Cornelius Vanderbilt cut all rail connections into Manhattan in January — mid-winter — strangling the city's supply lines until Albany capitulated.