The Incredible Journey of Jimmy Winkfield
James “Jimmy” Winkfield was born in 1882, the youngest of 17 children, in Chilesburg, Kentucky a few miles outside of Lexington. By age seven, he supposedly was secretly riding his neighbors’ saddle horses bareback, and longingly watching the Thoroughbreds running in the adjacent fields. At age 10, Jimmy became an orphan and was taken in by a sister in Lexington who lived near the Kentucky Association track.
Jimmy Winkfield at 19. Photo courtesy Keeneland Library
By 1898 Jimmy was working as a stable boy and exercise rider for trainer “Bub” May. May had been impressed with Jimmy’s affinity for horses and the skills he showed as an exercise rider. On-the-side, he began working with the teenager, teaching him the finer points he would need to know to become a jockey. In August, 1898 May loaded up his horses and headed to Chicago for the meet at the Hawthorne track. Jimmy was included in his entourage. On August 10th, May informed the 16-year-old Winkfield that he would be the rider on Jockey Joe in the card’s sixth race. Jimmy would finally ride in a real race.
It proved to be an inauspicious beginning to what would become a stellar career. The other five jockeys were professionals, and not really concerned about the chances of the young stable boy. Jimmy got off to a slow start but had eventually joined the rest of the pack. May had advised him not to swing wide when passing other horses, but to be patient and look for a hole to open up closer to the rail. As they passed the half-mile post Jockey Joe had moved into third. and was moving smoothly. Jimmy tried to force Jockey Joe through the tight opening bumping into another horse and sending the jockey over the rail. While he went on to finish second, he was immediately called to the judge’s stand and banished from riding for a year.
In 1902 New Orleans, a black boxer, George Dixon, easily defeated a white fighter to win the featherweight championship. In the following day’s editorial in the Times-Democrat that objected to the interracial bout: “We of the South who know the fallacy and danger of this doctrine of race equality, who are opposed to placing the negro on any terms of equality, who have insisted on a separation of the races in church, hotel, car, saloon and theatre; who believe that the law ought to step in and forever forbid the idea of equality by making marriages between them illegal, are heartily opposed to any arrangement encouraging this equality, which gives negroes false ideas and dangerous beliefs.” Their statement was a reflection of mood of the nation.
The Supreme Court’s decision in Plessy vs. Ferguson of 1896 essentially legalized "separate but equal” discrimination against African Americans. With the court’s blessing, pressure soon mounted to ban African Americans from all integrated sporting events, including racing.
By the dawn of the 20th century, racism was beginning to threaten the careers of all Black jockeys. Those collecting the largest purses became its biggest targets. Economic factors and anti-gambling sentiment had also impacted the black riders. Racing and the number of rides available for all jockeys had dropped dramatically. By 1908 the number of American tracks dropped from 315 to 25. The writing was on the wall. American horse racing, and all involved in it were in dire trouble.
In 1900 Jimmy’s ban expired and he experienced his first year of regular riding. Following an excellent first year, the press dubbed him “a gentleman on the ground, a demon in the saddle.” In 1901 he claimed 161 and was beginning to receive national recognition as an up-and-coming rider.
Late in the summer season, Winkfield was made painfully aware of the growing hostility against black riders. White jockeys at the Harlem track outside of Chicago, intentionally drove him into the inside rail, causing multiple injuries to both the horse and rider. The Chicago Record reported the incident as a “Jockey War at Chicago.” With increased competition for fewer rides and the growing strength of Jim Crow sentiment, the war between black and white riders was just beginning.
After the incident at the Harlem track, Jimmy needed a break before heading to New Orleans for their fall season. He headed home to Lexington for a brief rest. There, he met Edna Lee, who soon became his wife. Edna had hoped to start a family, but Jimmy was not interested. He explained that the rigors of his profession, and the unsuitability of the track-life for a lady, much less a family, made this impossible. They did use some of Jimmy’s earnings to buy a house near the track at 553 East Third Street, but after Jimmy returned to the circuit, he would seldom darken its door.
Winkfield exercising Alan A Dale prior to the 1902 Kentucky Derby. Photo courtesy Keeneland Library
In 1901 he claimed 161 victories and was drawing comparison with his idol, Isaac Murphy. After winning his second consecutive Kentucky Derby in 1902, one of only five jockeys to accomplish that feat, he moved on to Chicago. Sam Hildreth, a prominent owner and trainer, wanted Jimmy to ride his great horse McChesney in the $20,000 American Derby. Feeling that McChesney needed more work, Hildreth reluctantly entered him in the Derby Trial at the Harlem track. McChesney was the class of the field, and noted for being a tough horse which helped offset Hildreth’s fear of injury. Jimmy, who had ridden him previously, would be his jockey. As they approached the half-mile pole, a horse that was two lengths ahead of McChesney suddenly stopped and went down. With nowhere to go and no time to stop, Jimmy attempted to jump over the injured horse but McChesney caught a leg on the downed horse and did a full somersault, landing on his rump and throwing Jimmy into the inner rail. The horse fared better than his rider who was lying unconscious in the middle of the track with broken bones sticking through his pants. Some weeks later, his doctor broke the news that he might never ride again.
Winkfield on McChesney in Chicago, 1901. Photo courtesy Keeneland Library
Jimmy was a mental and physical wreck and knew he needed help and where to find it. As soon as he felt strong enough, he was on a train to Lexington and Edna. She proved to be a caring nurse, and relished her role as a dutiful wife and caretaker. For the first time, they had a true marriage. With Edna’s help and that of a dedicated black physician, James Allen, Jimmy began to regain his strength and confidence. As the time approached for Jimmy to return to the track, he told his wife that in the future things would be different. While sincere when spoken, this was not to be. When it came down to it, Jimmy loved his horses more than any person.
By 1903, Winkfield was acutely aware of the growing racism in his industry and Jim Crow’s impact on his country. He also saw a number of first-class jockeys who were taking their talents overseas.
After scoring wins against horses owned by some of racing’s most successful bluebloods at the Saratoga meet, legendary owner and trainer, John Madden, signed Jimmy to ride his horse Minute Man in America’s richest race, the Futurity at Sheepshead Bay. Winkfield felt his ship had finally come in. Soon after, he received a better offer from another trainer and decided to take it. This broke his contract with Madden and one of racing’s strongest unwritten rules. Jimmy wound up finishing third with Madden’s horse coming in sixth. Madden was furious and had clout, and he effectively had Jimmy blackballed from riding in all big money races on New York tracks. Jimmy knew he had made a serious mistake and later admitted; “I got too smart for my pants.”
Having been nearly killed by white riders, receiving death threats, being blackballed by John Madden, and facing ever-shrinking opportunities to ride, Jimmy decided it was time to look at his options. in 1904 the 22-year-old Winkfield decided to take his talents to Europe.
With the help of trainer Jack Keene, he first went to Poland to help Keene with his horses. Soon after, he was able to land a lucrative contract to ride in Czarist Russia. When he climbed the gang-plank of his ship to Europe, Edna was not with him. Their relationship had slipped back to past habits, and the decision for her to remain in Lexington was mutual. Edna would later accompany her husband twice to Russia, but didn’t speak Russian and was not comfortable with her husband’s lavish life style and friends. In his own way Jimmy had tried, but the ending was inevitable. In 1910, on one of Jimmy’s rare visits to Lexington, the couple had a horrible fight that ended when Jimmy stormed out vowing to never return. In 1911, Edna filed for divorce which was granted that summer. Jimmy did not contest, and it is thought that Edna was provided with a generous settlement.
Winkfield in Europe
Winkfield was somewhat of a curiosity in Russia, and was surprised to find that the racism he faced at home was non-existent here. His success on the track was instant and amazing. His friends included aristocrats and racing's elite, and he was soon earning an annual income comparable to $100,000 in American dollars. In his first year of riding in Russia, he won 51% of his races and was the leading rider in the country. He became known as the “Black Maestro,” and was always invited to the finest parties in Moscow.
“Jimmy Winkfield after winning the Grosse Preis von Baden in Germany in 1910”. Oil on canvas by Wojciech Kossak. Courtesy of the International Museum of the Horse. Kentucky Horse Park
Jimmy was not confined to riding in Russia alone — he also rode in major races in Poland, Germany and Austria. A list of his significant triumphs included three Emperor’s Prizes, two Empress Prizes, two Moscow Derbies, four All-Russian Derbies, the Grosse Preis von Baden, and two Warsaw Derbies.
Marriage to Alexandria
Jimmy was now entrenched with Moscow’s social elite, spending most of his free time in their company. Here he met and became enthralled with Alexandria Yalovicina, the 19-year-old daughter of a high-ranking cavalry officer. The attraction was mutual, and the couple was soon married. Shortly thereafter Alexandria presented Jimmy with his first son, George, named after Jimmy’s father.
The Trek from Odessa
By 1917, an ominous cloud appeared on the horizon with the beginning of the Russian Revolution. As the war intensified, it was decided to move all of the racehorses west from St. Petersburg and Moscow to Odessa in Ukraine. Jimmy followed the horses, leaving Alexandria and George in Moscow. Two years later, the Bolsheviks had swept across the country and were on the outskirts of Odessa. Winkfield and the other horsemen realized that if the prize Thoroughbreds were left at the track, that they would be killed and eaten by the advancing Red Army. Jimmy had unsuccessfully tried to contact Alexandria in Moscow, and assumed that his family had either been killed or captured. The horsemen at the Odessa track decided to drive the 260 prize horses over 1,100 miles in the dead of winter to Warsaw. Jimmy became one of the leaders of the drive. Remarkably, they arrived in Warsaw that spring with 250 emaciated but uninjured horses. Jimmy and some of the other horsemen stayed on at the track to try to nurse the horses back to health and were rewarded by seeing many of the once starving Thoroughbreds return to the track.
Starting Over
In the forced exit from Russia, Jimmy lost everything, including his second wife and their son. Most of his wealth had been in czarist bonds, which were now worthless. While still convalescing from his trek across Europe, Jimmy was contacted by a former client he had ridden for in Russia. He had fled the Bolsheviks to Paris with most of his fortune intact and resumed his passion for racing. Now he wanted Winkfield to ride for him again. Jimmy was soon on a train to Paris.
In France, he again rode with notable success with major wins in the Prix du Président de la Republique, the Prix Eugène Adam, and the Grand Prix de Deauville. The French loved Jimmy and affectionately called him “le Blackman.” Assuming that his wife and son had been killed in the Revolution, he married the daughter of a wealthy Russian Barron, who as a wedding present built the couple a chateau and private stables in Maisions-Lafitte on the outskirts of Paris. Eleven months later, Lydie gave birth to Jimmy’s second son, Robert. The next October, Liliane, his first daughter arrived following a difficult delivery by Lydie.
Liliane never shared her brothers’ and father’s fascination with horses. When time came for high school she wished to return to America, choosing Cincinnati as her destination. She was an honor student in high school and finished her degree at Fisk University in three years. While at Fisk, she met and married an equally gifted medical student, Dr. Edmund Casey. Upon graduation the couple returned to Cincinnati where he became a prominent surgeon.
In 1923 the Winkfields were surprised when his second wife Alexandria and son George showed up at their door. For over five years they had witnessed the horrors of the revolution, been stripped of their wealth and status, and suffered for their family’s support of the czar.
Alexandria was a shadow of her former self, barely able to recognize her former husband. The visit put a tremendous strain on Jimmy and Lydie’s marriage, as neither had considered that Alexandria was still alive. It also brought back Jimmy’s guilt at having abandoned his family in Moscow. Alexandria’s condition was such that Jimmy and George decided to place her in a sanitarium. George remained with Lydie and Jimmy. Once again, Jimmy’s inability to deal with his family responsibilities had come back to haunt him. With George, who had inherited his love of horses, Jimmy hoped that he might become to become a good father.
George and Jimmy did develop a close relationship and Jimmy guided him through the many steps it would take to become a jockey. He was finally able to secure his jockey apprentice license and won a few races during the next two years. But when George started to have problems maintaining his weight, he was forced to give up his dream of being a race rider and settle for training with his dad. Over the next few years, George experienced periods of depression and heavy drinking. This eventually led to George’s death in a bar room brawl at age 25.
By 1930, age and weight were taking their toll on Jimmy’s riding career. He had been a jockey at the highest level for 30 years when the approximate length of an American jockey’s career in the saddle was four. By his count, he had won 2,300 races.
The decision was made to hang up his saddle and switch to training with his Lydie’s son Robert. Robert, as had Jimmy’s son George, had inherited his father’s love of horses. As trainers, both Winkfields were quite respectable, winning the Grand Prix du Paris, while most of the important French classic races evaded them.
For the remainder of the decade, Jimmy enjoyed working with the horses and getting to know his family. All of this was shattered on June 14, 1940, when Nazi troops marched into Paris. They remained for the next four years. The Winkfield chateau and stables were occupied by German soldiers. Jimmy had hoped he could hold on in France, but after a year under Nazi rule, he and his family decided to flee to the US.to the U.S. Once again most of the family’s savings was lost in the process.
Return to America
The family arrived in New York, and Jimmy started looking work, hopefully with horses. But it seemed that his country had forgotten the man who had won two Kentucky Derbies forty years earlier, and had been so successful in Europe. The best he could do was land a job running a jackhammer for the WPA on the streets of Queens — a strange position for the five-foot-tall, 130-pound man.
Eventually, Robert found a horse owner who was looking for help at his winter training quarters in South Carolina. Jimmy was hired and, leaving Lydie in New York, he and Robert headed to the heart of the segregated south. Once there, he assumed the duties of a stable boy. After so many years in Europe, Jimmy was shocked at the condition of African Americans in South Carolina. Jim Crow had certainly done his job.
War’s End
When the war ended, Jimmy considered immediately returning to Paris. But he had accumulated debts in America that needed to be paid. He was able to find some training work with American owners and decided to start yet another comeback here. In 1949, the small stable he and his son Robert were training for, picked up an unheralded gelding named Little Rocket. For the next four years, he turned out to be a cash cow for the Winkfields. In 1953, with their debts settled and some cash in their pockets, it was time to return to Paris.
Once in Paris, he was able to regain possession of his Chateau which had been confiscated by the Germans during the war. For the next three years, he re-established his stable and again was training horses. In 1956, he decided it was time to turn the training over to his son Robert, but stayed on as an advisor.
Final Trip Home
In the spring of 1961, Jimmy again returned to America seeking advice for a medical condition that he feared could be fatal. He visited family and friends in Lexington and then went to Cincinnati where he stayed with his youngest daughter, Lillian. After learning his illness was not serious, Jimmy accepted an invitation from the National Turf Writers Association for him and Lillian to attend the Kentucky Derby, and to be their guests at a Derby eve dinner at Louisville's prestigious Brown Hotel. The last Kentucky Derby he had seen was from a saddle in 1903.
Jimmy and Lillian arrived at the Hotel at the appointed time and approached the Brown's front doors. There they were confronted by the doorman who informed them that because of their color, they could only enter through a rear door. While someone from the dinner was able to secure entrance for the Winkfields, it proved to Jimmy that many of the problems that had forced his decision to leave for Europe in 1904 still persisted in his native state and country.
Passing
Jimmy Winkfield returned to Paris after the Derby, never to return to his native country and state again. died peaceably at his chateau at Maisons-Lafitte in 1974. In 2004, he became one of four Black horsemen from Lexington, Kentucky to be inducted into the National Museum of Racing Hall of Fame.
Conclusion:
Jimmy Winkfield was an amazing but flawed man. He reigned as one of the greatest riders to ever mount a Thoroughbred on two continents at a time when Blacks were being forced off American tracks and out of American sports. By his own count, he had won some 2,300 races He was associated with some of the most influential events of the 19th and 20th century, losing two fortunes in the process. He had great intellect. From the tiny village of Chilesburg, Kentucky, orphaned at 10, and with only a seventh-grade education, he taught himself four languages and rubbed shoulders with Europe’s elite.
Jimmy Winkfield was most comfortable with horses. He loved and understood them and they trusted him in return. While he loved his families, they would always be secondary to the horses and his life on the track. He was unable or unwilling to reject many of the temptations that came with his success. Maybe this stemmed from his childhood or lack of male role models, maybe from his sudden wealth and status, or maybe it was just flaws in his character. In any case, he remains a remarkable man from a remarkable time. To paraphrase what he had once said, "He'd come a long way from Chilesburg, Kentucky.”
Bill Cooke, Director Emeritus, International Museum of the Horse (retired) Vice President, Phoenix Rising Lexington 7-15-2019 – revised 5-16-2023