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This group failed miserably and Gambler returned to prison. Gambler was one of the original members of the Injustice Society, which planned to kill the Justice Society and control the United States. Another time he helped an art collector commit insurance fraud, coming into conflict with Starman and Sandman. At one time, he won a gambling vessel and armed it to the teeth. Gambler clashed with Green Lantern many more times over the years. This incapacitated the crowd and allowed him to escape. In another escape, Gambler bribed the executioner at his own electrocution to rig the floor to be electrocuted instead of the chair. He used the real Dickles as a hostage to escape Green Lantern.

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In the confusion, Gambler managed to escape, as well as to free all of the inmates of the prison.

The Gambler had used his mastery of disguise to confuse Green Lantern. When the hero arrived to search the prison, he was surprised to see his friend Doiby Dickles in a cell. Perhaps his boldest escape was in 1946 when he wrote a note to Green Lantern telling the hero that he would escape prison and then daring the hero to stop him. Gambler, like most criminals in comics, was extremely adept at escaping from prison. Gambler was imprisoned in the Gotham Penitentiary. Green Lantern was finally able to catch the Gambler at a horse race where Gambler had turned the horses towards the crowd to cover his escape. The Gambler eluded Green Lantern twice using his special Derringer, which could fire ammonia or blackout gas in addition to real bullets. He was spotted in Gotham City by Green Lantern while standing next to his own wanted poster. Growing bored, he moved East to the big cities. He started off robbing trains and small town banks. Sharpe was immediately successful as a criminal. Embarking at last upon his new career of crime, the Gambler quickly became one of the most wanted men in the country. Over the next several years, Steven spent time with a traveling carnival, learning the art of makeup and becoming an expert with throwing knives and pistols. When an armored car crashed right in front of him as a result of a freak accident, Steven decided to help himself to the money that had spilled out of the back of the van, vowing that from then on he would take whatever he could get.Ĭonvinced that the only thing that mattered in his life was luck, and that the lucky people were those who took chances, Steven drank a toast to his grandfather's memory-and to his own new life as the Gambler. When Helen ran off with a local boy who had won a fortune gambling on the sweepstakes, Steven quit his job and decided to make a new life for himself. The day after his high school graduation, young Steven Sharpe III asked his girlfriend, Helen, to marry him, but she refused until he could prove he was not a habitual gambler like his father and grandfather before him.