By Spencer Jakab
Who is the greatest investor of all time? Just like in sports, it isn't a simple matter of comparing stats. For example, most younger basketball fans insist all-time points leader LeBron James is the so-called G.O.A.T., partly because they can still see him play. But plenty argue that Michael Jordan's star shined brighter, especially on the championship stage.
We have selected five of the greatest investors of all time. Like those hoops legends, some plied their trade in eras when the rules and the competition were easier in certain ways, much tougher in others. But they were all playing the same game: Turning a dollar into lots more.
Read my profiles of five picks for the investing GOAT and then cast your vote. When you're done, share it on social media with the hashtag: #GOATinvestor. And be sure to tell me in the comments if I've overlooked your favorite investor or if you have another candidate I failed to list.
I'll be sharing my thoughts on the results in WSJ's Markets A.M. newsletter. Sign up here -- it's free. Voting will be open until Dec. 18.
Peter Lynch
Ask middle-aged or older Americans how they got into investing and many will tell you that it was after reading the 1989 bestseller " One Up on Wall Street," by Peter Lynch. He taught a generation how to get rich slowly.
Lynch took over Fidelity's Magellan Fund when it had a mere $18 million in assets. By the time he retired 13 years later it had grown to $14 billion.
Lynch's mantra was "buy what you know," and boy, did it work for him. During a span that included two recessions, an energy crisis and the worst single day for U.S. stocks ever, his compound annual return was an almost unbelievable 29.2%. And he couldn't supercharge that by using borrowed money or selling stocks short like a hedge-fund manager.
Lynch also didn't achieve that through market timing or guessing when the next downturn would happen. He famously said: "If you spend 13 minutes a year on economics, you've wasted 10 minutes."
Jim Simons
Jim Simons was a leading mathematician, teaching at Harvard. Restless, he went to work for the government and cracked Soviet codes during the Cold War.
Then he wanted to try his hand at investing -- something he knew little about. After a few bumps, he put together the best record of any hedge fund in history, and it isn't even close.
Between 1988 and 2018, his Medallion Fund returned an astounding 66% gross. At that rate, one dollar would have turned into nearly $7 million before fees.
How did Simons do it? Other investors would love to know. His firm, Renaissance Technologies, hired scientists instead of financiers and looked for hidden patterns. Journal reporter Gregory Zuckerman told his fascinating story in "The Man Who Solved the Market."
Simons died last year at the age of 86 with an estimated $31 billion fortune that has largely gone to charity. As he put it: "I did a lot of math, I made a lot of money, and I gave almost all of it away. That's the story of my life."
Jesse Livermore
Jesse Livermore, nicknamed "The Boy Plunger," is considered by many to be the greatest trader who ever lived. A novel based on his exploits, " Reminiscences of a Stock Operator," remains a must-read for hedge fund trainees.
Livermore ran away from home at age 14 and got work as a "board boy," posting stock prices that came in on the telegraph. Noticing patterns, he placed his first stock trade the following year in a bucket shop -- more a gambling parlor than a brokerage. Livermore was so successful that he was soon banned from many of them.
As an adult, Livermore made legendary scores by going against the market. He had shorted stocks before the Panic of 1907, and banker J.P. Morgan personally asked him to close his positions. In the next two decades, he would twice go bankrupt and trade his way back to immense wealth.
In 1929, Livermore shorted stocks again, months ahead of the crash that October. He walked away with $100 million at the start of the Great Depression -- equivalent to nearly $2 billion in today's money.
Livermore is still widely quoted, but mostly as Larry Livingston, the fictional character from "Reminiscences." His own writings are worth considering for today's aspiring boy plungers in crypto and meme stocks:
"If there was any easy money lying around, no one would be forcing it into your pocket."
Hetty Green
Hetty Green was a bit like the Diana Taurasi of investing.
Haven't heard of Taurasi either? You should: She won six Olympic gold medals for the U.S. and is the all-time leading scorer in women's professional basketball. Taurasi retired this year as the league's oldest active player.
Green's investing prowess turned her into one of the richest people in America. Her gender may be the reason she is overlooked, but that makes her accomplishments all the more remarkable. Women couldn't vote or engage in many financial transactions without their husbands in her heyday, the late 19th and early 20th centuries.
Known as "The Witch of Wall Street" for her miserly ways, Green quietly bailed out New York City in the early 1900s. Among her financial coups was accumulating devalued U.S. currency, the original greenbacks, issued during the Civil War. Her bet paid off handsomely.
Green was one of the original value investors before that was a term.
"I buy when things are low and no one wants them. I keep them until they go up and people are crazy to get them," she once said.
It worked: Her wealth is estimated to have been as much as $5 billion in today's money.
Warren Buffett
We left the LeBron of investing for last.
Warren Buffett got started very young, buying his first stock at age 11.
A protégé of Benjamin Graham, the father of value investing, Buffett has since evolved beyond Graham's methods. At age 95, he will end a remarkable 60-year career running Berkshire Hathaway in December. A shareholder's 5,502,284% return since Buffett took over would have left them with 140 times as much money as just buying the S&P 500 stock index as of 2024.
Buffett is no longer the world's richest person, but only because he has donated many of his Berkshire shares to charity over the years. The generosity doesn't end with those causes. Buffett's annual letters have passed on invaluable wisdom about investing and life.
His advice for those who aspire to similar greatness: "If you like spending six to eight hours per week working on investments, do it. If you don't, then dollar-cost average into index funds."
Write to Spencer Jakab at Spencer.Jakab@wsj.com
(END) Dow Jones Newswires
December 12, 2025 05:30 ET (10:30 GMT)
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