He first gained attention in the railroad industry in 1954, when he orchestrated a successful proxy battle for control of the Minneapolis and St. Louis Railway.
Heineman remained in charge of the holding company Northwest Industries (owner of Fruit of the Loom, Acme Boots, and Velsicol Chemical Corporation) until 1985.
[2] Heineman is noted in the history of Chicago, Illinois, for replacing all the steam locomotives which brought passenger trains into North Western Station with diesel locomotives, in one day in 1956, in response to a complaint by Mayor Richard J. Daley about smoke and fumes emanating from the station.
Heineman served in various governmental roles in World War Two and was active in politics, working as a speechwriter for Adlai Stevenson in 1952, Chairman of the White House Conference on Civil Rights during the administration of Lyndon Johnson and Chairman of the Illinois Board of Higher Education.
Heineman turned down several offers from President Johnson to serve in high-ranking positions including Budget Director and UN Ambassador, but remained an informal advisor.