Jack McGurn

Jack McGurn was one of gangster Al Capone's most feared and ruthless killers. He picked up the nickname "Machine Gun" because of his proficiency with the new Thompson sub-machine gun - aka Tommy Gun - favored by Chicago gangsters. McGurn - born Vincenzo DeMora -didn't seem bound for a life of crime as a youngster. Unlike many of his colleagues, he came from a middle-class background and had no run-ins with the law as a youth. That all changed the day his father was killed by a Chicago gang headed by the Genna family, for the crime of selling bootleg liquor without cutting the gang in on the action. The story is that the teenager dipped his hands in the blood of his father and swore to kill everyone who had anything to do with his murder. Too young and inexperienced to be hired into one of the gangs that ran Chicago at the time, McGurn spent the next few years sharpening his skills with a gun and toughening himself as a professional boxer, under the name "Battling Jack McGurn". When he decided the time was right, he got himself hired by the Capone mob, which was engaged in a deadly war with the Genna outfit. McGurn soon became Capone's top gun, and was credited with killing anywhere from 25 to 30 of Capone's rivals. Among the victims were six members of the Genna family who were involved in his father's murder. After McGurn killed each one, he would leave a nickel in his hand, signifying his contempt for men he considered "nickel and dimers". He soon became Capone's personal bodyguard, and Capone went nowhere without him. McGurn was suspected by Chicago police of having planned and carried out the infamous "St. Valentine's Day Massacre" in which seven members of the George Moran (aka "Bugs" Moran) mob - another of Capone's rivals - were machine-gunned to death in a Chicago garage (Moran himself said, when he found out about the massacre, "Nobody but Capone kills like that"). Although McGurn was brought in for questioning, his girlfriend provided an alibi for the morning of the murders. When it was later proved that she was lying, McGurn was arrested and charged with perjury. However, he got around that charge by marrying his girlfriend, thereby ensuring that she couldn't testify against him. McGurn also had an interest in several nightclubs, in one of which he had hired up-and-coming comic Joe E. Lewis to perform. When it came time for Lewis to renew his contract, he told McGurn that he had decided to accept an offer from another club. McGurn exploded and told Lewis he would never live to accept the offer. A few days later Lewis was attacked in his room by three men he recognized as McGurn associates. The men pistol-whipped him, beat him severely and one of them pulled out a large knife and proceeded to carve up Lewis' face, cut his throat and slice his tongue. Although severely injured, Lewis recovered, but it took him almost ten years to learn how to talk again. McGurn's fortunes began to wane in 1929, when Capone was sent to prison for income tax evasion. Many in Capone's gang feared and hated McGurn, and took the opportunity to strip him of his power and take away most of his legit businesses. His wife left him and he was reduced to getting involved in small-time narcotics deals, which at the time was an activity the mob forbade its members to become involved in.

Seven years after the "St. Valentine's Day Massacre" he masterminded, on the eve of St. Valentine's Day in 1936, he was gunned down in a bowling alley.