Born in Peel County, Ontario, Chudleigh received a Bachelor of Science degree from Michigan State University in 1985. He later worked for the Ministry of Agriculture, and owned an IGA store in the Niagara Region. From 1980 to 1995, he was the Executive Vice-President of the Ontario Food Processors Association.
He was first elected to the Ontario legislature in the provincial election of 1995, defeating Liberal Walt Elliot and incumbent New Democrat Noel Duignan in the riding of Halton North. He was re-elected in the redistributed riding of Halton in the 1999 provincial election, by a margin of over 20,000 votes over his closest opponent. The Progressive Conservative Party won both of these elections, although Chudleigh was never appointed to cabinet.
The Tories lost the provincial election of 2003, and Chudleigh was returned with a greatly reduced margin of victory. He endorsed Frank Klees's unsuccessful bid to lead the Progressive Conservative Party in 2004, and is currently the party's Deputy Whip.
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