As the Market Crashed in 1987, Paul Tudor Jones Made $100 Million in a Single Day: ‘The Most Important Rule of Trading Is to Play Great Defense, Not Great Offense’

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.

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.

Jones didn’t think it was a coincidence, and so he started to build bearish positions before the crash. By the time Black Monday rolled around, the value of his positions exploded. His hedge fund, the Tudor Investment Corporation, allegedly tripled in size over the course of a single trading session.

At first glance, it looks like the secret to Jones’ success is all about data and market predictions. But Jones has always seen things differently.

His philosophy is built around the assumption that most traders (even himself) get it wrong a lot of the time. That’s why his moves center more on controlling losses than they do on maximizing gains. In other words, capital has always got to come first, and profits are always second.

Jones often warns traders against averaging down on losing positions just because the prices look appetizing. He doesn’t get emotionally attached to past decisions and regularly reassesses whether the original thesis of his positions still holds true.

“Every day I assume every position I have is wrong,” he says.

“I know where my stop risk points are going to be. I do that so I can define my maximum possible drawdown. Hopefully, I spend the rest of the day enjoying positions that are going in my direction. If they are going against me, then I have a game plan for getting out.”

It might sound like a conservative approach, but it’s clearly the best way to avoid spectacular losses. That’s how he won big on Black Monday when everybody else went broke. And with all the market turmoil we’ve seen in recent months, this is an approach we could all learn from.

Why Risk Management Can Give You An Edge

This might sound like an ancient lesson in Wall Street history. After all, the tech has changed. Markets trade a lot faster than they used to, and AI can execute automated transactions in milliseconds. But the psychology behind Paul Tudor Jones and his $100 million win hasn’t changed at all.

Speculative bubbles are driven by greed, and panic selling is driven by fear.

When investors get overconfident, they try to talk themselves into believing history won’t repeat itself. But it always does. Every time the market corrects, investors make the same old mistakes. They spend too much time and too much money on fashionable sectors, ignore diversification, and treat every dip like a buying opportunity.

Sound familiar yet?

Unfortunately, the truth is that sometimes those dips are a catastrophe waiting to happen. Jones’ approach is all about ensuring you’ve still got a strong financial footing when those catastrophes do sneak up on you.

That doesn’t mean you’ve got to refuse to take risks or hide in cash. But you do have to understand how much risk you’re actually taking on, and that starts with diversification. It means paying close attention to position sizing and accepting that selling isn’t a failure. It preserves your capital and gives you flexibility for when something better comes along.

At the end of the day, Paul Tudor Jones didn’t become one of the hedge fund greats because he predicted a colossal crash one time. He became a legend by recognizing that markets are inherently uncertain. He’s spent decades sculpting his investment strategy around that hard truth, and that’s what he means by “playing great defense.”

It’s all well and good finding the next stock that doubles or triples. But Jones shows us that long-term success isn’t about making the boldest or sexiest trades. It’s about doing what you’ve got to do to protect your capital when everybody else is losing theirs.