By 1936, at age 24, Daddano had accumulated an extensive
criminal record in the 42-Gang, including nine counts of
bank robbery,
larceny and
auto theft. Giancana and Battaglia eventually recruited Daddano into the Chicago Outfit. In 1944, Daddano was arrested for attempting to steal three million war
ration stamps. While police suspected that the Outfit was behind this crime, Daddano refused to name his accomplices. After
World War II, Daddano became a leading enforcer for The Outfit. He also controlled illegal gambling operations in
Dupage,
Will and
Kane counties and in the Chicago suburbs of
Cicero and
Berwyn. Though a "
made man" and valued "
capo" in the Chicago Outfit. Daddano has been described as a "ruthless and pitiless killer" who was refined in torture with ice picks and blowtorches, keeping victims alive for hours while torturing them. Daddano was the main suspect in at least seven murders. ==Legitimate enterprises==