Anthony Perna was in trouble with the law beginning with a 1927 rape charge and conviction. Surprisingly his conviction was overturned and he was free to pursue his criminal life. Perna was later associated with the crime family run by Stefano and Antonio Magaddino in western New York. The Magaddino's were active in narcotics trafficking and gambling. Their territory extended west from Buffalo and Niagara Falls into southern Ontario and the Ohio Valley. Perna was also active in the bootlegging business in the 1930s.