Career
He most recently played for Schwenninger Wild Wings of the Deutsche Eishockey Liga (DEL). During the 2005-2006 season he played two games for the New York Islanders and two more in the 2007-2008 season for the Phoenix Coyotes. Prior to his professional career, Caldwell was an All-American defenceman and captained the University of Denver Pioneers to the 2004 National Collegiate Athletic Association Championship.
After two seasons in the Master of Science-liiga with Ässät, Caldwell signed with fellow Finnish club, Lukko Rauma.
During the 2012-2013 season, he was mutually released from his contract and returned to the German DEL, with Eisbären Berlin. On May 7, 2013, Caldwell was signed as a free agent to a two-year contract with the Thomas Sabo Ice Tigers.
In August 2014, Caldwell and the Ice Tigers mutually agreed to terminate his contract. On August 26, 2014, the Schwenninger Wild Wings announced they had signed Caldwell.
In the 2014-2015 season, Caldwell contributed with 23 points in 52 games from the blueline, however was unable to lift the Wild Wings into the playoffs.
On March 7, 2015, the Wild Wings opted not to offer Caldwell a new contract, rendering him a free agent.