Born in Buffalo, New York, Tronolone was arrested three times before the age of 21. In 1975, he was convicted of operating a bookmaking operation with an estimated weekly income exceeding $1 million; Tronolone was sentenced to two years imprisonment with a $2,000 fine. At some point, Tronolone became an active member of the Cleveland family. However, Tronolone maintained his family responsibilities from his residence in Florida, where he also operated a travel agency. Tronolone was also closely associated with the Buffalo crime family of New York.