Before entering public life, Wilkinson was a financial planner in Stratford. He is a Certified Financial Planner and a founder of Wilkinson & Keller Financial Planning Ltd, and is Past President of the Perth-Huron chapter of Advocis, his professional association. He also worked as the finance chair of his church organization for seven years. In 2002, he was awarded the Julia Award from the Canadian Cystic Fibrosis Association for his volunteer work.
Wilkinson first ran for the Ontario legislature in the 1999 election, losing to Progressive Conservative incumbent Bert Johnson by just over 6000 votes. In the 2003 election, he defeated Johnson by about 1500 votes in a rematch. Wilkinson's victory was regarded by many as a surprise; the Perth--Middlesex riding is culturally conservative, and many neighbouring rural ridings in southwestern Ontario returned Tory candidates in this electoral cycle.
The Liberals won the election, and on May 21, 2004 Wilkinson was named parliamentary assistant to Leona Dombrowsky, the Minister of the Environment.
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