In 1913, the republican Ossenberg “machine” backed Bosse’s campaign for mayor of Evansville. They did the same thing in 1916, when they helped Bosse win re-election. However, when prohibition came to Indiana in April 1918, the Ossenbergs abruptly severed their ties with Mayor Bosse, with the elder Ossenberg brother eventually resigning from his position in Bosse’s administration as head of Evansville’s police detectives.

Federal agents had their take on why the Ossenbergs and Bosse had a falling out: