His father, George Bennett, was a city councillor from 1971 to 1980, and his father-in-law, Keith Brown, was a Progressive Conservative Member of Provincial Parliament (MPP) from 1959 to 1967.
[8] He organized a campaign for local businesses affected by a major flood in mid-2004 and shortly thereafter was named as person of the year by the Greater Peterborough Chamber of Commerce.
[9] In the 2003 provincial election, Bennett co-chaired the unsuccessful re-election campaign of Progressive Conservative incumbent Gary Stewart.
[11] Bennett challenged one-term incumbent mayor Paul Ayotte in the 2010 Peterborough municipal election and won by a significant margin.
Bennett's supporters included former MPPs Keith Brown, John Turner, and Gary Stewart, as well as prominent municipal politician Paul Rexe (who died before the election).