Often described as shrewd and cunning. Milano led a gang known as the Mayfield Road Mob, a dangerous group of powerful criminals who ran Cleveland's numbers, drug and prostitution operations. Milano would later successfully merge his gang with another known as the "Licatese faction" led by John DeMarco and The Combination (he local Jewish Syndicate) which resulted in the formation of the Cleveland La Cosa Nostra family. Milano expanded the crime family's influence into gambling, loansharking and fledgling labor unions, as the end of Prohibition came along. Such post-Prohibition organized crime activities became the mainstay operations of the Cleveland crime family for decades to come. Milano was the boss of the Cleveland crime family from 1930 until 1935. His predecessor, Joseph Porrello,