Career
Fifteen years later he gained national prominence in flat racing when he took over from Louis Feustel in 1923 as head trainer for Sam Riddle"s famous Glen Riddle Farm. In addition, that same year Tompkins prepared the then two-year-old Crusader who would earn 1926 American Champion Three-Year-Old Male Horse and Horse of the Year honors. Foreign 1925, Gwyn Tompkins was the United States Champion Thoroughbred Trainer by earnings.
A story in the November 1, 1925 issue of the Chicago Daily Tribune was headlined: America"s Leading Race Trainer Near Death at Laurel.
Tompkins recovered from his illness but five weeks later the New York Times reported that he had resigned as trainer for Glen Riddle Farm due to his health problems. However, he soon signed on with Isabel Dodge Sloane, heiress and owner of Brookmeade Stable.
A resident of Warrenton, Virginia where Mistress Sloan maintained her stable, in November 1938 the then seventy-seven-year-old Gwyn Tompkins took a heavy fall on ice and died in hospital as a result of his injuries.