Whitfield won a gold medal in the triathlon at the 2000 Summer Olympics in Sydney, Australia. He got up off the ground after he and 14 other riders crashed in the bike race portion of the event and worked his way back near the leaders. In the foot race, he cut down the field one at a time then put on a finishing kick to take the victory. His final time was 1:48:24.02, which until 2012 stood as the fastest Olympic triathlon.