As a bootlegger, Rothkopf traveled widely, and supervised alcohol production for the "Cleveland Four," also known as the Cleveland Syndicate. Rothkopf is credited with the "erection and operation of the largest illegal distilleries ever found in the United States." Rothkopf and Max Diamond were convicted of tax evasion over liquor sales and sentenced to four years imprisonment and fined $5,000 in 1937. The trial showed they had failed to pay taxes on US$150,000 sales of illegal alcohol. and was connected to the Jungle Inn, located near
Youngstown, Ohio. He was also an investor in gambling businesses in Kentucky and Ohio. In 1936, alongside
Moe Dalitz,
Morris Kleinman and
Sam Tucker, Rothkopf invested in the
River Downs and
Thistledown racetracks in Ohio. With Morris Kleinman, Rothkopf was asked to testify before the Senate Crime Investigation Committee chaired by
Tennessee Senator
Estes Kefauver on bootlegging allegations in 1952. When both men refused because they didn't want the media to attend their hearing, they were first charged with
contempt of Congress and later cleared. ==Personal life and death==