Out of the Shadows: A Biographical History of African American Athletes

1. Jimmy Winkfield: The “Black Maestro” of the Racetrack

Jimmy Winkfield, photographed here in his racing silks, is considered the last of the great black jockeys. (Keeneland-Cook, Keeneland Library) 1WIGGINS_pages_i-132.qxd 9/12/06 11:46 AM Page 6 1 Jimmy Winkfield The “Black Maestro” of the Racetrack S U S A N H A M B U R G E R In many respects, Jimmy Winkfield’s career as a jockey mirrored that of many other outstanding African American athletes of the late nineteenth and early twentieth centuries in that he was grudgingly acknowledged at home in the United States, while revered as a champion in Europe. He managed to enjoy a long racing career, first as a jockey then later as a trainer, well beyond the age when most jockeys retire. Through two world wars and the Great Depression, Winkfield survived and succeeded—because of, despite, and regardless of his race. Horse racing in America enjoyed a long history parallel with the young country. Brought over from England with the colonists, the sport appealed to all classes and races while participation at various levels sorted out among these selfsame divisions. Eighteenth- and nineteenthcentury racing saw owners and breeders of racehorses come from the moneyed upper classes. During the era of racing as a gentleman’s sport, some owners also trained their own horses. As the sport moved from an avocation to a business, the ranks of trainers arose from the lower classes—farm boys with minimal formal education or opportunity to better themselves. As a predominantly rural sport transplanted to the fringes of urban areas, horse racing attracted farm youth to the track in search of jobs in a milieu with which they were familiar. The primary theory, still accepted today, is that the jockey’s weight is a major factor in slowing a horse’s speed and endurance. The early race riders—sometimes the full-size adult owner, sometimes a young stable boy—soon demonstrated that the smaller and lighter-weight jockeys won more races than their larger, heavier counterparts. To gain a 1WIGGINS_pages_i-132.qxd 9/12/06 11:46 AM Page 7 competitive edge, owners and trainers started using smaller men and young boys to ride their racehorses. As the breeding industry developed in the southern states of Maryland, Virginia, and Kentucky with limestone-enhanced water and grass to develop strong bones in young horses, so too did the apprenticeship of jockeys. Prior to the American Civil War, most of the southern jockeys were slaves. After the war, these same men continued in the profession as successful riders at tracks in the border and northern states before the southern economy recovered enough for racetracks to flourish there again. From New Orleans to Cincinnati, black jockeys dominated the sport. But with the rise of Jim Crow and the competition for rapidly increasing paychecks from winning races, white riders insinuated themselves into the black-dominated profession and, by fear and intimidation , began to squeeze out African American jockeys until the only black faces seen on the track were either in the grandstand betting on the horses or working at menial jobs tending horses on the backstretch. At a time when African American jockeys reigned supreme on the American turf, Jimmy Winkfield (1880–1974) began his rise to racing stardom only to be stymied by racism and the decline of horse racing in the early 1900s. His determination to continue riding sent him to Czarist Russia, Poland, and France as a jockey, then to the United States and back to France as a trainer of thoroughbreds. Throughout his long life and rollercoaster career, Winkfield exhibited the perseverance of an indomitable will to survive and to succeed. The youngest of seventeen children, Winkfield learned to ride saddle horses on the farms near where his parents sharecropped tobacco and hemp in Chilesburg, Kentucky. Orphaned at ten, Winkfield left his home and went to live with his older sister in Lexington, Kentucky, the center of the state’s—and the nation’s—horse racing and breeding. Surrounded by successful black jockeys such as James “Soup” Perkins and three-time Kentucky Derby winner Isaac “Ike” Murphy, Winkfield saw much to admire as he worked his first job shining shoes. The supportive environment reinforced a strong sense of self-worth and pride. Winkfield respected Murphy’s honesty and integrity and learned a valuable lesson about a strategy for making money in the profession. Murphy, considered a “money rider...