Early Life and Career
Caldwell was born in Brandon, Manitoba. He holds a Bachelor of Arts degree from Brandon University (1982) and a Bachelor of Education degree from Queen's University in Kingston (1983), and has taken graduate studies in History at McGill University. He returned to Brandon as an adult, worked as a substitute teacher, and was active with community organizations such as the Brandon Folk Music and Art Festival, the Brandon Poverty Forum and the Art Gallery of Southwestern Manitoba.
Caldwell was a member of the Brandon city council from 1992 to 1999, representing the Rosser Ward (Ward Two). He was a founding director of the Brandon Regional Health Authority, and an Executive Member of the Union of Manitoba Municipalities, the Manitoba Association of Urban Municipalities and the Association of Manitoba Municipalities between 1997 and 1999. He opposed tax increases while on council, and supported owners of single-family homes in calling for parts of the city to be re-zoned from high-density residential to low-density residential. In 1998, he led a movement to establish a $50,000 reserve fund for social development.
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