Born in Haverford, Pennsylvania, on February 18, 1930, Freeman was named after the man who raised his father (Theodore Cullen Donovan), as well as his maternal grandfather (Thomas Cordy Wilson). He was one of five children. Raised in Lewes, Delaware, he attended Lewes Elementary School from 1936 to 1944. His father was a farmer and his brother a carpenter, and it seemed as if he would also have a blue collar career. When Freeman and his brother were young, they saved up money so they could take plane rides. He also was a part-time worker, helping to refuel the planes and work on them. He spent most of his money on flying lessons, and with over 450 hours of flying on his training record, earned his pilot’s license by the age of 16. “I sort of grew up at the airport,” Freeman said.