[3][4] After graduating, Di Ianni moved with his wife Janet (Ginetta) and three children, Robert, Paul and Stephanie, to Stoney Creek.
In early March 2003, Di Ianni was approached by members of the Ontario Liberals, including then-Premier Dalton McGuinty, in an effort to convince him to run provincially against Labour Minister Brad Clark.
On April 28, 2003, Di Ianni announced he would seek the office of mayor indicating that he believed Hamilton to be at a crossroads with regard to development.
[9] Speaking to reporters, Di Ianni noted he was immensely happy that the voters of Hamilton elected their first Italian-Canadian mayor by such a large margin.
[10] Di Ianni's term as mayor saw him attempt to enact his mayoral platform by addressing such issues as the completion of the Red Hill Expressway, business tax reduction, airport development, improving relations among the amalgamated municipalities, and obtaining additional social service funding from the more senior levels of government.