In the last years of the 19th century and the early years of the 20th, American gambling was dominated by men who were usually as rich, or richer, than Selfridge or Citroen, and whose exploits at the gaming tables of New York, Chicago, New Orleans, and elsewhere have never been rivaled since.  Losses of $25,000 on a single hand of cards or roll of dice were considered fairly common-place in the gambling houses of these cities; many of the tycoons who frequented these houses uncomplainingly lost hundreds of thousands a year.  These men were top industrialists, financiers, stock marketers, and multimillionaires; among them were such internationally famous names as the young heir to a fortune Reginald Vanderbilt, the industrialist Henry C. Frick, and the judge (later, the steel magnate ) Elbert H. Gary.
One figure seems to have been especially predominant in this world of tycoon gambling- a man whose name was respectably associated with Wall Street and the high echelons of the steel industry, but whose nickname proved his eminence among gambles: John W.  “Bet-a-million” Gates.
Gates was unquestionably one of the great gamblers of all time.  He would quite literally bet any amount on anything against anybody.  He would play poker with an upward limit on bets of $ 50,000 as readily as with a limit of one dollar; he would play bridge for $ 1,000 a point.  Once he was invited to play poker with some overconfident gamblers who felt that their purse of $ 35,000 was quite a considerable basis for protracted session of play.  Gates shocked them by suggesting that they toss a coin for the whole amount.  If no cards, dice, roulette wheels, etc., were available, Gates would happily toss coins for practically any sum; or he would bet on raindrops sliding down a window.  (Once on a train in 1897 he won $22,000 backing the right raindrops.)
Before Gates achieved his industrial wealth and gambling glory, he had been a simple barbed-wire salesman in Texas.  But he rose rapidly as a businessman and stock-market operator; and at the height of his career he was several times a millionaire, thanks to his role in the organization of the American Steel and Wire Company and U.S. Steel, and his interests in copper mines and railroads.  He also had interests in circuses-appropriately, since his gambling fame was sufficient to make him almost a one-man circus.  What Bet-a-million Gates had won or lost the night before was considered important news not only throughout America but in Britain and Europe as well.
There are various stories and legends describing the way Gates got his nickname.  One of the these concerns a types of racing exploit in 1900: Gates had entered a horse of his own in a race, and had backed it with a total of $ 70,000 in bets.  The horse won, and Gates collected $600,000.  The rumor of this win spread, and (as such rumors will ) became exaggerated: Eventually, according to this legend, it was being said that Gates had ‘bet a million” and had won over $2,000,000.
Another version (which I find somewhat more enjoyable, and which seems to fit with Gates’ expensive personality) also involves a race-track bet.  An official at a track supposedly asked Gates to limit  his bets to $ 10,000 a time.  According to this story, Gates resented this attempt to inhibit his enjoyment, and circulated through the crowd offering to bet anyone a million dollars on any one horse.  He didn’t get anyone to take the bet; but he did get a nickname.
Such dramatic gestures ascribed to Gates (whether or not they happened ) helped to earn him a reputation for reckless, hot-headed gambling.  And later stories, when New York was blazing with the exploits of its millionaire gamblers, increased his reputation.  Gates had one day in the summer of 1902 visited the Saratoga race track and had lost around $ 375,000.  (Racing was one of his favorite gambles, but he lost at the track more often than he won.) After dinner he went to the Club House (which was a gambling casino owned by Richard Canfield, New York’s leading gambling impresario) and began playing game of faro .

At first Gates played under the usual house limits of $ 500 for bets on single cards and $ 1000 for “doubles.”  He lost a few times, then suggested that the game be made private and the limits raised to $2500 and $ 5000.  He continued to lost lose under these conditions, and in a few hours had dropped $ 150,000 in the game (making a total of $ 525,000 lost, including his racing defeats, that day). 
But he didn’t give up.  Instead, he pushed the limits up to $ 5000 and $ 10,000 and continued to bet furiously.  Then his luck changed: He shortly won back the $ 150,000 and had won an additional $ 150,000 by the time the game ended –thus having cut his losses for the day to the relatively small figure of $225,000.
Gates enjoyed poker as much as faro, and in this game also maintained his name as an impetuous gambler.  A pot in a Gates poker game might reach anywhere from $ 50,000 to $200,000; Gates himself lost nearly $ 1,000,000 in about one year’s poker playing (1899-1900).  But, according to most authorities, in spite of these gargantuan figures, Gates was not just a devil-may-care millionaire who threw his money away for the sake of gambling’s excitement.  He was shrewd, cool, and analytical both at business and at the gaming table; all his risks were well calculated, the odds against winning well assessed.  He didn’t plunge without taking a long, hard look at his chances; but when he felt they were favorable, he plunged wholeheartedly.  Of course, he often suffered immense losses; but he also often won heavily, and generally stayed ahead of the game.
Like any skillful gambler, Gates would try to gain the advantage however he could.  He was quite capable of such deceptions as betting astronomical sums on a weak poker hand to frighten opponents out of the game; and sometimes he used slightly more dubious tricks, such as inviting a group of jockeys to dinner, wining and dining them, and picking up enough tips from their unguarded conversations to win more than $200,000 at the next day’s races.  But such sharp practice is far from cheating; and it can be quite safely said that Gates was never a cheat.
The Gates stayed ahead of the game in every respect is proved by the fact that he remained a multimillionaire all his life.  But he didn’t always remain a gambler.  One of the last stories told of him described a visit he paid in 1909 (when he was 54) to a Church conference in Texas, where he addressed the gathering on the evils of gambling.  He warned them not to play cards or dice, not to bet on horses, and not to speculate on the stock exchange.  But one warning he offered them seems rather a paradoxical statement for a man to make who had apparently given up gambling: He told the conference: “Don’t be a gambler; once a gambler, always a gambler.”

If Gates did give up gambling before 1910, then he got out just in time.  Because by then a man named Arnold Rothstein was beginning to become prominent in the American baseball gambling world-and in several less attractive worlds.  Rothstein’s prominence, as a gambler or otherwise, was notoriety not fame: He was a gambling cheat and a racketeer, a major figure in the underworld that practically ran New York in the two decades from 1910 to 1930.

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