Born in Italy, Megale moved to Connecticut as a young man. Megale attended Post University in Waterbury, Connecticut for two years before dropping out. Megale's current residence is Stamford, Connecticut. In 1990, Megale pleaded guilty to racketeering and was sentenced to six years in prison. Megale's plea deal included an admission that he belonged to a La Cosa Nostra family, which infuriated Gambino boss John Gotti. In 1995, Megale was released from prison on parole. However, in 1998 he returned to prison for 11 months for associating with other criminals, a parole violation.