He was the godfather of future Cleveland crime family underboss Angelo Lonardo.
Anthony Milano founded the Italian American Brotherhood Club in 1928 in Cleveland’s Murray Hill neighborhood.
Milano and his brother Frank were active in Black Hand extortion and bootlegging during prohibition.
His younger brother Frank was leader of the "Mayfield Road Mob", an Italian gang that fought the Porrello crime family for control of criminal rackets in Ohio.
Milano had significant control over several local labor unions in Cleveland due to his connection to Jackie Presser.