According to his reminiscences, Caldwell's early skiing career began while he was at Dartmouth College when he had an opportunity to participate in the World Nordic Championships in Nordic Combined skiing (both cross-country and ski-jumping). He entered the U.S. Navy through Dartmouth ROTC and was detailed to continue his skiing career.
According to his recollections, Caldwell's initial skiing career started at Dartmouth College when he had a chance to participate in the World Nordic Championships in Nordic Combined skiing (both cross-country and ski-jumping). He joined the U.S. Navy through Dartmouth ROTC and was assigned to continue his skiing career.