Raymond G. "Raymie" Woolfe Jr., of Troy, Va., died May 10 in Charlottesville. Born in New York, N.Y., July 31, 1935, he was the son of trainer Raymond G. Woolfe Sr., and Ruth Ferguson Woolfe.
While in high school in Camden, S.C., Woolfe made racing history Aug. 30, 1951, at Saratoga Race Course, where he became the youngest jockey at the time to win a stakes at a New York track. Only 16, he won the Saratoga Steeplechase Handicap on Hampton Roads, trained by his father and owned by Marion duPont Scott. New York sportswriters wrote of famed jockey Eddie Arcaro carrying "the kid's" saddle from the winner's circle.
"The most applause I've seen a rider get for some time went to Ray Woolfe Jr. after he came back successfully in the Saratoga Springs Handicap," wrote Joe Palmer in The Blood-Horse. "He's just 16 ... and a nice kid into the bargain, and even people who had lost their money seemed glad that he had won."
Woolfe grew up riding hunters and jumpers. The first mount he had as a jockey was on Hampton Roads Aug. 23, 1951, in the Beverwyck Steeplechase Handicap, in which he finished second to Oedipus, who was considered the best jumper in New York at the time.
Woolfe attended the University of Virginia and was a member of the polo team before he joined the U.S. Marines. After he left the Corps as a sergeant, he graduated from the University of South Carolina School of Journalism and became a photojournalist. An apprenticeship with famed New York fashion and Kennedy family photographer Mark Shaw gave Woolfe experience shooting for advertising, fashion, society, and celebrity print layouts. In 1968 he covered the Chicago Democratic National Convention and the ensuing riots, according to his family.
Before long, his love of Thoroughbred racing drew him back to a job at Daily Racing Form. During his time with DRF, he wrote an acclaimed book on 1973 Triple Crown winner Secretariat. He also wrote the well-received book Steeplechasing, published in 1981. In 2016 his highly praised Doomed Horse Soldiers of Bataan—The Incredible Stand of the 26th Cavalry was published, with a moving foreword by the late Col. Edwin P. Ramsey, of the 26th Cavalry.
Woolfe is survived by two daughters, Shannon Virginia Woolfe of Snow Camp, N.C., and Laurie Ferguson Woolfe, of Decatur, Ga.; and a sister, Ruth (Tudy) Bunn, of Oceanside, Calif.
His ashes were scattered the afternoon of May 17 where his beloved dogs are buried, next to the pond on his farm in Troy, Va.
Donations in Woolfe's memory will be gratefully accepted by The American Steeplechase Injured Jockeys Fund, c/o Colvin G Ryan, 22359 Polecat Hill Rd, Middleburg, Va., 20117-3273; or the National Steeplechase Museum, 200 Knights Hill Rd., Camden, S.C., 29020.