His sister Mary worked for the City of Toronto and is the widow of Ron Ross, a successful high school teacher.
After graduating, he joined the City of Toronto's clerk's department and rose to the position of protocol officer (public relations director).
In 2003, Flynn's son, Tim, ran unsuccessfully in Ward 25 (Don Valley West) for a seat on Toronto City Council.
However, following a complaint by former Etobicoke reeve Henry Oscar Waffle,[1] he was disqualified by a county court judge after the fact for having been an employee of the City of Toronto on nomination and election day.
[4] He ran for a seat on the newly amalgamated Toronto City Council in 1997, but finished third behind Gloria Lindsay Luby and Mario Giansante.