Caldwell, who coached the Trinity College freshman lightweights to the unofficial national championship in 1975, took over for Bill Austin as the Head of the Marist Rowing program in 1976.

Caldwell started rowing at Yale, where he was the coxswain of the Varsity Heavyweights for three years. Upon graduation from Yale took a teaching job for which he coached in the afternoon.

Caldwell got his start in coaching at Trinity University. A coach who is well respected by his peers, Caldwell compiled a 55-7 record in four years at Trinity and never had a Freshman boat lower than third at the Dad Vails. In 1976 Caldwell came to Marist and ran the program for two years. After Marist, Caldwell went on to the Head Coach position at Tufts University, where he remained until 2016.

In the early ’90s, Caldwell became involved with the IRA board. He became involved in the administration of events and ultimately was appointed commissioner of the IRA, the 51-member school, rowing association that has been around since 1895. When he retired from his coaching position at Tufts, he remained in the commissioner role with the IRA.