Following losing an election for the New York Senate in 1994, Gentile first won public office in 1996, when he was able to capitalize upon internal divisions within the Republican Party and win a three-way race for the 23rd District in the New York State Senate.
Gentile was the Democratic candidate for New York's 11th congressional district special election, 2015 He lost to Republican Richmond County District Attorney Daniel M. Donovan, Jr. Green Party candidate, James Lane, came in third.