Lester Cutler started out as a swimmer, competing at the University of Iowa. In 1960 he finished fifth at the US Olympic Trials in the 100 metre backstroke. He studied dentistry at Iowa but left that to study education and eventually became a teacher. He kept swimming, trying for the 1964 Olympic team, but did not make that team. In 1965 he switched to canoeing in kayaks, and in 1967, Cutler spent the summer in Sweden to learn techniques and training methods. He later became a high school teacher in Costa Mesa, California.