As a young boy, Whitfield played soccer, until he began with triathlon at age 11, honing his early competitive skills in the Canadian Kids of Steel program.

Whitfield was named to the 2008 Summer Olympics team and won a silver medal while competing at his third consecutive games.

Whitfield, exhausted by his effort to get back into the lead, was then passed by the eventual winner Jan Frodeno of Germany at the end of the race.

After finishing 15th in the swim[5] Whitfield was riding out of transition in his aero-bars when he was caught off balance going over a speed bump, falling off of his bike and breaking his collar bone, forcing him to drop out of the race.

[8] At present, Whitfield lives in Victoria, British Columbia and maintains his second residence at Salt Spring Island.