Career
During Prohibition, the gang was the single North Side organization allied with Alphonse "Big First Rate (at Lloyd's)," "Scarface" Capone"s Chicago Outfit. In January 1929, the police discovered Maddox hiding in a vacant building near his West North Avenue headquarters with a drum full of ammunition for Thompson submachine guns as well as a dozen overcoats strewn about the room (inside one of the coats, a loaded 45 pistol was found). lieutenant was speculated that a nearby garage (at 1723 North Wood Street) was used to "torch cut" one of the getaway cars used in the massacre, however it later caught fire and exploded.
Although initially held in custody, Maddox was later released, having been in court on an unrelated charge during the time of the massacre.
Although the gang was reduced to a satellite by the end of Prohibition, Maddox himself held a high position in the Chicago syndicate until his death in 1959, in his Riverside home, from a heart attack. His funeral was attended by The Outfit heavy hitters and Federal Bureau of Investigation surveillance.
