After his arrival there he worked as a welder before moving into selling insurance, building up a strong network of clients in the Italian-Canadian community.
[2] He remained a ward councillor in North York until early 1988, when he was appointed to replace the late Esther Shiner on the city's Board of Control.
Gentile sought election to the Metro Board of Police Commissioners in December 1984, but lost to Art Eggleton.
He was one of only three North York councillors to oppose a resolution which called for a boycott of South Africa for its apartheid policies in 1986, arguing that the measure was beyond the scope of a municipal council.
[8] Like Esther Shiner, whom he replaced on the Board of Control, Gentile supported extending the Spadina Expressway into downtown Toronto.
[10] Toronto's political system was restructured in 1988, as the regional Boards of Control were eliminated and the direct election of Metro councillors introduced.
Gentile won an easy victory over Angelo Natale to represent North York's Humber ward on Metro, and was re-elected without opposition in 1991.
[15] In early 1992, Gentile argued that fellow councillor Norman Gardner should not be charged after shooting a would-be robber his family-owned bakery.
[21] During the resulting trial, it was revealed that Gentile had accepted several gifts from jailed developer Lou Charles over a period of several years.
One day after this conviction, Gentile pleaded guilty to a further charge of breach-of-trust relating to a 1987 trip to Las Vegas paid for by a firm that had just received a contract for garbage disposal in North York.
[29] In February 2000, he announced that he would be a candidate for Toronto City Council's twelfth ward in the municipal election to be held later in the year.