The world’s greatest investors: Leon Levy
Leon Levy made a fortune from betting against the crowd.

Who was he?
Leon Levy was born in 1925 in Manhattan. He studied psychology at City College of New York (CCNY), although his grades were too low to join the advanced securities analysis course. He served in the US Army, then joined Hirsch & Company as a research analyst in 1948. In 1950 he left to help a colleague, Max Oppenheimer, set up on his own. Levy became a managing partner in 1959, and helped Oppenheimer grow into a successful mutual fund firm, before it was sold in 1982 for $165m. Levy then set up hedge fund Odyssey Partners with Jack Nash. They ran it for 15 years, until he retired in 1997.
What was his strategy?
As a contrarian, Levy invested in companies that he felt were undervalued. In some cases he sought out the shares and bonds of companies that were in bankruptcy proceedings, betting that they would either survive the process or that sufficient value would be left after the liquidation to make it worthwhile. After he retired, he made $100m by short-selling the tech-heavy Nasdaq index at the peak of the dotcom bubble.
Did this work?
From 1982 to 1997, Odyssey returned an annual average of 22% (turning $10,000 into $794,175) versus 16.9% for the market. The fund grew to have assets of around $3bn ($4.5bn today), compared with $50m on launch. Levy's own fortune was put at $750m just before his death in 2003, despite extensive philanthropic donations, including a $100m gift to Bard College.
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What were his biggest successes?
While at Hirsch, Levy bought Pacific Western Oil and Jefferson Lake Sulfur, noting that both stocks had seen significant purchases by directors. His profits from these deals brought him to Oppenheimer's attention. In 1983 Odyssey Partners made headlines when it bought a stake in the parent company of a bankrupt railroad. Levy rightly believed that high energy prices would boost demand for coal (and thus rail freight). Meanwhile, the sale of the railroad's undervalued timberland and real-estate assets delivered a $200m profit for Odyssey.
What lessons are there for investors?
Levy's record shows that it often pays to bet against the crowd, and that academic ability (or lack of it) is not always a bar to success thanks to his success on Wall Street, he was invited to return to CCNY as a guest teacher.
Matthew graduated from the University of Durham in 2004; he then gained an MSc, followed by a PhD at the London School of Economics.
He has previously written for a wide range of publications, including the Guardian and the Economist, and also helped to run a newsletter on terrorism. He has spent time at Lehman Brothers, Citigroup and the consultancy Lombard Street Research.
Matthew is the author of Superinvestors: Lessons from the greatest investors in history, published by Harriman House, which has been translated into several languages. His second book, Investing Explained: The Accessible Guide to Building an Investment Portfolio, is published by Kogan Page.
As senior writer, he writes the shares and politics & economics pages, as well as weekly Blowing It and Great Frauds in History columns He also writes a fortnightly reviews page and trading tips, as well as regular cover stories and multi-page investment focus features.
Follow Matthew on Twitter: @DrMatthewPartri
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