Gentile was born in Siculiana, a small village on the south coast of Sicily in the province of Agrigento. He immigrated to the United States arriving in New York at age 18, in 1903. He quickly associated with the Black Hand during the early 20th century, Gentile would become a leader in America's early mafia and would later serve as a confidant for New York mobsters throughout the early part of the 20th century up until the Castellammarese War and the subsequent formation of New York's Five Families under Lucky Luciano in 1931. Gentile traveled the country as a troubleshooter and negotiator, known as the messaggero or substituto, relaying messages between crime families and mediating disputes and became part of a New York Mafia Family led by Vincent Mangano and Joseph Biondo, which later b