1993: As a backroom boy for PC Party of Canada, closely associated with "Is this the face of a Prime Minister" negative ad against Chretien.
2003: Ran admittedly a decent campaign for mayor (apart from MillerHighwayRobbery.com), and had a lot of broad support.
2004: Wins leadership of Ontario PCs, has trouble getting seat.
2007: Loses in Leaside in general election.
2009: Loses in Haliburton-Victoria-Brock by-election.