Following his release in 1941, Wortman briefly worked as a steamfitter before organizing an army of gunmen whose ranks included "Black" Charlie Harris, Elmer Sylvester "Dutch" Dowling, and brothers Monroe and Tony Armes.
He also established legitimate businesses, including trucking firms and taverns, run by his younger brother Ted.
Ted lived on a horse farm on Illinois Route 157 on the north end of Caseyville, about one mile (1.6 km) from the elder Wortman.
During the 1960s, a Black street gang known as The Warlords began moving in on Wortman's territory, and in one incident threw a hand grenade into McCoy's Tavern.
Although his power began to decline in his later years, suffering financial losses from legal battles and closure of gambling operations, Wortman remained in control of southern Illinois gambling until his death on August 3, 1968, at age 63, in Alexian Brothers Hospital due to complications from surgery for laryngeal cancer.
Ironically, Wortman lies some 3.6 meters (12 ft) from his chief nemesis, East St. Louis policeman Robert "Tree" Sweeney, who killed 12 men in the line of duty.