‘The Most Important Rule of Trading Is to Play Great Defense, Not Great Offense’

Bear market by Champc vi iStock It doesn’t take a genius to make money in a bull market. But if you want to come out on top during a crash, you’ve really got to know your stuff. That’s what separates casual investors and newbies from the Wall Street legends. Think about it: Michael Burry won…


‘The Most Important Rule of Trading Is to Play Great Defense, Not Great Offense’
Bear market by Champc vi iStock
Bear market by Champc vi iStock

It doesn’t take a genius to make money in a bull market. But if you want to come out on top during a crash, you’ve really got to know your stuff. That’s what separates casual investors and newbies from the Wall Street legends.

Think about it: Michael Burry won betting against the housing bubble before the global meltdown of 2008. Warren Buffet built his huge fortune buying when everybody else was selling. Then, there’s hedge fund billionaire Paul Tudor Jones.

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He might not be a household name, but Jones offers a textbook lesson in how a wise investor profits off market panic. On October 19, 1987, the Dow Jones Industrial Average suffered its biggest single-day drop in history. It was so bad that anybody who can still remember that day calls it “Black Monday.”

Billions of dollars worth of wealth evaporated into thin air, and some traders lost everything over the course of just a few hours. But after the dust all settled, it turned out Paul Tudor Jones hadn’t lost a dime. In fact, he’d made $100 million in a single day by betting against the collapsing market.

How’d he do it? Years of disciplined risk management.

“The most important rule of trading is to play great defense,” Jones has always argued. “Not great offense.”

Almost 40 years later, that piece of advice has never been more relevant. We’re wrestling with out-of-control inflation, sluggish growth, geopolitical turmoil, and everything in between. So, what does “great defense” actually look like?

Why Defense Always Beats Offense

To contextualize just how big this win was, let’s set the scene. The stock market had been enjoying a huge rally up until the autumn of 1987. Valuations had ballooned, investor optimism was high, and everybody thought the bull market was just going to keep on running.

Everybody, that is, but Paul Tudor Jones.

Jones started diving deeper into historical market comparisons with market strategist Peter Borish, and the pair noticed disturbing similarities between the stock market crash of 1929 and the price movements that had been happening throughout the late 1980s.

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