01Jesse LivermoreHe 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.Wikipedia ↗g79700%Card
02George SorosOn 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.Wikipedia ↗g751400%Card
03Hetty GreenWorth $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.Wikipedia ↗g741400%Card
04Jay GouldJay 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.Wikipedia ↗g71700%Card
05Ivan BoeskyIvan 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.Wikipedia ↗g67000%
06Long-Term Capital ManagementLong-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.Wikipedia ↗g67000%Card
07Renaissance TechnologiesJim 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.Wikipedia ↗g67000%Card
08Daniel DrewDaniel 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.Wikipedia ↗g661000%Card
09Paul Tudor JonesPaul 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.Wikipedia ↗g66800%Card
10Cornelius VanderbiltWhen 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.Wikipedia ↗g641000%Card