Terry "Machine Gun" Druggan (1903 – March 4, 1954) was an Irish-American mobster and leader of the Chicago based mob - the Valley Gang during prohibition. Druggan was well-known throughout the Chicago area as a tough street fighter. In 1919, Terry Druggan took over the Valley Gang. Druggan was a dwarf-like little man with a hair trigger temper and a lisp. Druggan was ambitious and found the Valley territory to restrictive for his high ambitions and soon extended his criminal reach far beyond its borders. By 1924, Terry Druggan could truthfully boast that even the lowest member of his gang wore silk shirts and had chauffeurs for their new Rolls Royce.

Druggan was smart enough to enter into several lucrative business agreements with Johnny Torrio and was wise enough to pull the Valley Gang off the streets and remodel them after Johnny Torrio's restructured version of Big Jim Colosimo's outfit. With his booze millions, Druggan bought a magnificent home on Lake Zurich and a winter estate in Florida. He surrounded himself with yes-men and flunkies and parked 12 new cars in his garage. He had a swimming pool but he couldn't swim, a tennis court but he didn't play the game, dairy cattle, which he admitted scared him, sheep and swine in his pastures. He owned a thoroughbred racing stable and raced his horses at Chicago's tracks, the horses draped in his family's ancient Celtic color scheme.

One time, when he was ruled off the turf at one track for fixing the race, Druggan pulled his gun on the officials and promised to kill them all then and there, if they didn't change their ruling. They changed their ruling.

With the end of Prohibition, the Druggan and Lake gang, as the Valley Gang was then called, was completely saturated into the Chicago syndicate's operations and for all given purposes, ceased to exist.

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