Napoli was known as a "Gentleman's Gentleman". Intelligent and well-respected, Napoli maintained ties to most of the major crime families.[citation needed]
Jimmy Nap used Crisci’s Restaurant as a base for his job activities.[3]
In 1969, Napoli was indicted for fixing several boxing matches. In the 1970s, Napoli reportedly operated the largest numbers operation in the United States. By 1976, the operation allegedly employed 2,000 people and grossed over $150 million a year. Napoli apparently ran this huge operation from a lounge in the Greenpoint section of Brooklyn. In 1978, Napoli was convicted for gambling and sentenced to five years in federal prison.[4]
Napoli was married Grace Perrota from November 29, 1933 until her death in 1962, they had 5 kids,(4 sons, 1 daughter)later got remarried to Jeanne Napoli, a former night club singer and theatrical producer. They had 2 daughters. In 1984, Napoli invested $250,000 in an unsuccessful musical biography of actress Marilyn Monroe that starred Jeanne.[6]