The names of Terry McCaleb's parents are not known. His father hoped to become a professional baseball player. He played shortstop and second base. In 1950 he was able to get a tryout with the Chicago Cubs who at that time held their spring training on Catalina Island which was owned by William Wrigley Jr., owner of the Cubs. He didn't make the team but he and his wife decided to stay on Catalina. The father worked for the Wrigleys, first on their ranch and later on their large yacht. He started as a deckhand and worked his way up to skipper. After some years as skipper for the Wrigleys, he wanted to get his own boat. The Wrigley family financed his purchase of The Following Sea, which he operated as a charter fishing boat. When Terry was about seven years old, his mother became disenchanted with life on Catalina and returned to Chicago. Terry stayed on the island with his father. When his father was dying of cancer, Terry moved him to a mainland nursing home in order to be able to visit him more often. After his father's death, Terry scattered his ashes at sea around Catalina Island.