Terry Druggan

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Terry "Machine Gun" Druggan (1903 – March 4, 1954) was an Irish-American mobster and leader of the Chicago based Valley Gang from 1919 and through the prohibition era.

Druggan was very small in stature, with an explosive temper and a lisp, and was well known throughout the Chicago area as a tough street fighter. He was also ambitious, and worked to extend his criminal reach beyond the Valley territory. By 1924, Druggan's gang was successful enough that even the most junior members wore silk shirts and travelled in Rolls Royce cars with chauffeurs.

Druggan entered into several lucrative business agreements with Johnny Torrio, and pulled the Valley Gang off the streets and remodelled them after Johnny Torrio's restructured version of Jim Colosimo's outfit. With the fortune he made during prohibition, Druggan bought a lavish residence on Lake Zurich and a winter estate in Florida, and owned 12 new cars. He had a swimming pool and tennis court, though he could not swim or play tennis, and kept dairy cattle, sheep, and pigs in his pastures.

He owned a thoroughbred racing stable and raced his horses at Chicago's tracks, the horses wearing his family's ancient Celtic color scheme. On one occasion, when he was disqualified at one track for fixing the race, Druggan pulled a gun on the officials and threatened to kill them all 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 ceased to exist independently.

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