Conn N. McCreary was born on June 17, 1921 in St. Louis, Missouri. He was the son of John McCreary. After graduating from high school in St. Louis, McCreary traveled to Lexington, Ky. , hoping to make his fortune at the racetrack. His mother had bought him a bus ticket, and had pinned inside his jacket a note declaring that her son had permission to travel.
Once in Lexington, he set out on foot for Dixiana Farms, a bluegrass training ground he had heard about. He was given a ride that day by Steve Judge, a noted trainer for the Woodvale Farm of Royce G. Martin, who hired him immediately as a stable boy. McCreary soon became a jockey and never left racing. McCreary rode in 8, 802 races and produced 1, 251 winners during a twenty-one-year career from 1939 to 1959. His mounts earned a total of $7, 822, 624. Although he won his first race in 1939 at Chicago's Arlington Park, his first big win came in 1941 in the Blue Grass Stakes, where he rode Our Boots to victory over Whirlaway, the horse that would set a Kentucky Derby record ten days later and go on to win the Triple Crown. Aboard Pensive in 1944, McCreary won the Kentucky Derby and the Preakness, but fell short of the Triple Crown when he was beaten in a photo finish with Bounding Home in the Belmont Stakes. In the Derby, he came from thirteenth place to win the contest. McCreary's life as a jockey was marked by both hot and cold streaks. His career seemed to end in 1950, when a succession of losses caused him to hang up his tack. A comeback attempt in 1951 seemed equally futile until Broadway restaurateur Jack Amiel entered the picture. His three-year-old colt, Count Turf, a none-too-promising son of 1943 Triple Crown winner Count Fleet, had won only sprint races and was a "field horse" in the Derby. Even Count Turf's trainer had given up, refusing to travel to Kentucky for the race. McCreary rode Count Turf to a Kentucky Derby win, taking the lead in the stretch and winning by four lengths going away. Returning to New York City by train, McCreary and Amiel admired the gold cup.
The next year, Churchill Downs began the custom of presenting the winning jockey with a replica of the Kentucky Derby winner's cup. McCreary's second Derby win ended the long slump for the jockey, who returned to form as one of the top thoroughbred riders of the day. Among his later triumphs were the Flamingo and Preakness on Blue Man in 1952, and the Palm Beach and Widener handicaps at Hialeah, in Florida, in 1953 on Oil Capital. He was also successful riding Stymie, a noted stretch-run horse whose abilities matched McCreary's talents. His Second and final retirement from riding came in 1959. He continued riding for the next month before headaches forced him to a doctor in Miami, where X-rays revealed he had a fractured skull. After his retirement from riding, McCreary remained active in horse racing as a trainer from 1960 until 1968, when poor health forced him to retire. Horses trained by McCreary included the champion Irish Rebellion, and the stakes winners Mara Lark and Selari's Miss. At the time of his induction, he was working in the press box of Calder Park in Miami, Fla. He remained in Florida, working in the publicity departments of various Miami racetracks over the years, and was in the process of moving to Ocala when he died of a heart attack.
Known as the "Mighty Mite" and "Convertible Conn, " he stood four feet, two inches tall and weighed just ninety pounds at the beginning of his racing career. He was noted for his ability to save a horse until late in a race, gaining a reputation as a come-from-behind rider. Although he earned fame for his dramatic stretch runs, which required perfect timing, he was equally adept at taking a lead early and holding it for an entire race. He took several bad falls as a rider, including one at Aqueduct racetrack in New York in 1944, in which he landed on his head.
McCreary was married twice. He had four children with his first wife, Norma, and two with his second wife, Dorothy.
