In the 2000 Canadian federal election, Caldwell was the Canadian Alliance candidate in the Toronto riding of St. Paul's, ending up in third place after the Progressive Conservative candidate and the Liberal candidate who won the riding.
In the 2000 Canadian federal election, Caldwell was the candidate for the Canadian Alliance in the Toronto riding of St. Paul's. Caldwell arrived in third place with 4,515 votes (11.7%), behind Barry Cline, the Progressive Conservative candidate and Carolyn Bennett, the Liberal candidate who won the riding.