Jesse Livermore: The Greatest Trader Who Ever Lived

When Jesse Livermore made his first stock trade at the tender age of 15, he didn’t hedge his bets. He consulted the charts he’d compiled working as a chalkboard runner in a Boston brokerage firm, and when the figures for the company in question, Burlington, checked out, he went all in, investing everything he had—all $5—in the railroad. Two days later, he cashed in his shares, for a profit of $3.12.

It was 1892.

Exhilarating, that first taste. The pendulum had begun to swing.

Livermore began to roam the streets of Beantown, frequenting its bucket shops, gambling counters that took bets on stocks without executing actual trades. His ability to recognize patterns in the ticker tape stood him in good stead. In six months, he’d accumulated $1,000. Five years later, it was $10,000—enough to make him persona non grata to every pseudo-broker in the city.

So he moved to New York and graduated to trading with real Wall Street firms. Something, however, was wrong. His system wasn’t delivering as expected. He watched his stake drop, first to $2,500, then to zero. At an age when most contemporary youth were still preoccupied with fraternity smokers and petting, the “Boy Plunger” (turn-of-the-century slang for “reckless gambler”) had already gone through a full cycle of boom and bust.

Livermore decided the problem lay in the lag time between the stock order and the execution of the purchase itself. So he borrowed $500 against future gains. The pendulum began to swing wider. Quickly making back what he’d lost, he increased his stash further, to $50,000. Then, on May 9, 1901, he lost it all, every penny, largely due to the frenzied pace of the day’s trading.

Again he hit the bucket shops, again accumulating a stake that allowed him to get back into the game. He returned to New York with what he termed a “fair-sized roll.” Then, on April 16, 1906, he was hit by a premonition. With no warning, he yielded to a strange urge to sell short a thousand shares of Union Pacific railroad—an urge even he admitted he didn’t understand. Two days later, the San Francisco Earthquake hit. Union Pacific was decimated; he’d made $250,000 literally overnight. Inexplicable, the sudden intuition, but just as inexplicable was what happened next: again trading in shares of Union Pacific, he violated two of his most cherished principles—never heed insider information, and always keep your own counsel—and sold short when a friend tipped him off that the stock was about to tank. It didn’t. His net loss: more than $40,000.

The arcs described by the pendulum continued to widen, the swings to grow ever more vertiginous. During the Panic of 1907, Livermore again shorted the market, earning $1 million in the course of a few days. He then proceeded to lose everything in an attempt to corner the cotton sector, declaring bankruptcy and running up debts of over $1 million by 1916. Once again, he amassed sufficient capital to recover, making first $3 million (in assorted commodities), then $10 million (in wheat). Then came his greatest moment: sensing the impending 1929 crash, he again shorted the market, emerging from the rubble of October 29 with a net profit of $100 million—well over a billion dollars in today’s money.

Five years later, he was bankrupt, his vast fortune completely wiped out, for reasons that remain mysterious even today.

Livermore rallied from his subsequent depression in the late 30s, pooling sufficient energy to write a book detailing his trading principles. But on November 20, 1940, the pendulum swung finally, irrevocably against him. In the cloakroom of the Sherry Netherland Hotel in Midtown Manhattan, he shot himself in the head with a .32 Colt automatic. A suicide note was found scribbled in his notebook: “I am a failure,” it said.

Who was Jesse Livermore? How could the world’s greatest trader, the author of one of the most staggering fortunes America had ever seen, end up hitting the wall in just five years? What drove him to take ever more manic risks with his trades, to the point where the harmonic oscillator of his own speculations ended by ripping him apart?

Livermore himself gives us a clue to his own mystery in Reminiscences of a Stock Operator, the book of interviews he wrote with the journalist Edwin Lefèvre:

The speculator’s chief enemies are always boring from within. It is inseparable from human nature to hope and to fear….The successful trader has to fight these two deep-seated instincts. He has to reverse what you might call his natural impulses. Instead of hoping he must fear; instead of fearing he must hope….It is absolutely wrong to gamble in stocks the way the average man does.

The great trader liked to style himself as a dispassionate analyst. Repeatedly in Reminiscences, we find him stepping back from the welter of the trading floor to admonish himself with conclusions drawn from his market smash-ups—conclusions that read like oracular utterances brought down from the sacred mount of traders: “I learned you must give up trying to catch the last eighth, or the first: these two are the most expensive eighths in the world,” and the like. But the excerpt above intimates that perhaps cold-blooded calculation wasn’t the whole story. That beneath the rational exterior lay something that was not rational, that had to do instead with dreams and forebodings and hidden compulsions. That this aloof, seemingly imperturbable man was in fact deeply attuned to the obscure rumblings of chaos.

For chaotic his life was, in spades. His broker, reflecting on his penchant for cruising the Manhattan streets at night in his canary-yellow Rolls Royce in search of young girls, quipped, “When Livermore is speculating, he is thinking of screwing, and when he is screwing he is thinking of speculating.” His first wife, Nettie Jordan, separated from him one year after their wedding, following a tearful scene in which he begged her to pawn her jewels to finance one of his bankruptcies. His second wife, Dorothy Wendt, was an 18-year-old Ziegfield Follies showgirl who responded to Livermore’s philandering by taking up with a Prohibition agent; after separating from both men, she went on to shoot her 16-year-old son, Jesse, Jr., through the chest with a .22-caliber rifle. Both Livermore’s son and his grandson were manic-depressive and suffered from alcoholism. Both committed suicide.

Nor was chaos a mere by-product of Livermore’s personal eccentricities—it was his stock in trade. The Great Bear of Wall Street made his greatest profits when he sold short, that is to say, when he capitalized on other traders’ helplessness in the face of their own hopes and fears. In an age when Wall Street optimism was almost an American religion, he learned to read, and profit by, the dark anxieties that flowed just beneath the surface of the zeitgeist and that were liable to break out at any moment. He was an expert at sensing the nature and scope of mass hysteria, the thresholds at which men begin to panic. It’s no accident, then, that his favorite book was Extraordinary Popular Delusions and the Madness of Crowds, the Scottish philosopher Charles Mackay’s dark treatise on the power of the irrational in history. Nor is it an accident that, in seeking to harness the forces of unreason that he knew so intimately, he ended up betrayed by them—betrayed and, ultimately, destroyed.

The man who all his life sought to codify the workings of the market into a foolproof set of rules was the same man who consistently violated those rules, helpless to resist his own compulsions. The man who proclaimed clear-sighted analysis as the key to the charts was also a man haunted by irrational dreams and forebodings, who depended upon an uncanny sixth sense to tell him which way the market was moving, and who ultimately succumbed to the same delusions he fought so hard to keep at bay.

Traders are not the same as investors. Investors, however aggressive, are devotees of the long term. Personality-wise they tend to be more sober, more thoughtful and restrained, a la Warren Buffett or Peter Lynch. Volatility is, if not their enemy, then at best an unpredictable confederate, to be regarded with suspicion. Traders, by contrast, live in the moment. They operate by learning to feel the market, sensing when to cut their losses, when to double down, when to follow the trend and when to go against everyone. Far from being adverse to volatility, they secretly hope to get inside it, to understand it and so ride it to victory.

Like all traders, Livermore dreamed of beating the market, pinning his hopes to the forces of order: reason, logic, calculation, monetary self-discipline. Yet like all traders, he ultimately came face to face with that which cannot be rationalized, not just in the great hurly-burly of Wall Street but inside himself, in the shadowy realm where desire becomes compulsion and ambition self-destructive obsession. So that in the end, his battle with the market was a stand-in for his larger battle with himself.

Livermore was well aware of the chaos inside him. That’s why, early in his career, he invested in $800,000 worth of annuities for his wife and children that he himself would be unable to touch: “I knew a trading man will spend anything he can lay his hands on. By doing what I did my wife and child are safe from me.”

In the end, Livermore’s dream was the great, illusory dream of gamblers everywhere: to impose form and coherence on chance itself. But he failed to treat chance with the proper respect: he got too close. His story reads like a dark pendant to that other great 1920s story of lives lost to the pursuit of wealth, The Great Gatsby. Like Fitzgerald’s hero, Livermore sought to define himself against the huge forces that were shaping an America on the verge of empire. His failure, no less than Gatsby’s, is a grim parable of the fate of the individual in the age of money.

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Posted by on November 5th, 2013 at 9:03 am


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