Little lost and remade his legendary fortune multiple times before losing it for good in 1857;[note 1] although a great many owed him enormous debts, he was a generous creditor and never collected them, and at his deathbed in 1865 Little was penniless.

[2] The son of a successful local shipbuilder[5] and of Quaker origin,[6] Little exhibited a strong understanding of money and financial markets from an early age.

In the latter he would execute the opposite maneuver, corner a market by buying up all of the bonds of a particular company or sector, up-ticking the price so as to make a profit at the expense of any short sales based on those stocks.

[5] Hardworking, highly ambitious, and with his eyes set on the very top from the very beginning, Little commonly spent twelve hours a day working on such maneuvers in his office and a further six during the evening engaged in currency speculation.

Although theoretically he could have asked for more (he was, after all, in total control of the company), Little chose not to force the issue because he feared the resulting bankruptcies would destabilize the market potentially cause a collapse.

[5] By this time Little was already one of the richest men in America, accruing millions of dollars in security holdings through short sales, a market volume that made him the "Napoleon of the Board."

He was noted for being personally retired in manner, diffident except to business, in correspondence with most of the major economic voices of the nation, and a devout member of the Episcopal Church.

[11] This action (and others like it) was intensely unpopular with the other investors, however, and he was blackballed from entry in the New York Stock Exchange several times before regaining admittance.

Following the event, a rule was made to limit the length of any option contracts to sixty days,[4][8] to prevent a similar coup on the short side.

However, his fortunes were again reversed that year when he attempted but failed to corner the Norwich and Worcester Railroad and was obligated to pay out for thousands of inflated shares that he had himself bid up in price, losing about a million dollars in the process—a staggering sum at the time.

It was in these instances that Little most surely showed his strength of character; after each of his falls from fortune Little was able to rebuild his commercial empire, and even pay back his old contracts in full, leading some to remark that "Jacob Little's suspended papers were better than the checks of most men.

The Panic of 1857 completely blindsided the investor, who at the time was "long", possessing huge amounts of stock, much bought on the "margin" (on loan).

[5] A speculator to his very core, Little never put away any of his fortune to prepare for a rainy day; any money he made on the stock market, he immediately invested back into it.

[2] In his 1908 account on the early world of finance, Fifty Years in Wall Street, Henry Clews (who knew Little personally) penned that Little was "generous and liberal to a fault with his brother speculators who had experienced misfortune...remarkable for his great memory, he could easily remember all the operations he made in the course of a day without making a note or a mistake,"[13] and another stock market historian, Leonard Louis Levinson, said that he was "a nervous perfectionist who personally attended to every detail...kind, magnanimous, honorable, and a genius in market maneuvers.

A reflection on the Erie Railroad Company coup published by The New York Times in 1882 all but accused him of being a robber baron:[6] "He drove Wall-street before him just as in his earlier days he would have lashed a recalcitrant ox into obedience.

[7] Nonetheless for all of his wealth and innovation Little's ignominious end ensured he was quickly forgotten, and by the time Edwin Lefèvre published his now-classic Reminiscences of a Stock Operator in 1923 he was virtually unknown.