Story Time: Jimmy Winkfield, the Craziest Life You Don’t Know About

The name might be familiar, James “Jimmy” Winkfield is a dual-Kentucky Derby winner after all. In fact, he is the last African-American jockey to win the race! He rode His Eminence, and Alan-a-Dale to victory in 1901 and 1902. So he was a jockey more than 100 years ago, and died when he was 93 in 1974. Okay, so what makes this jockey’s story cool enough to talk about 113 years after his last Kentucky Derby win? Buckle your seatbelt because this is going to get intense real quick.

James Winkfield aboard the 1902 Kentucky Derby winner, Alan-a-Dale
James Winkfield aboard the 1902 Kentucky Derby winner, Alan-a-Dale

The year is 1901 and Jimmy Winkfield, a native of Kentucky, had won more than 160 races including the Kentucky Derby on His Eminence. This is post-Civil War America where racism was still a big part of the fiber of much of the country, with the Courier Journal referring to Winkfield as “a little chocolate colored negro.” With all the racing success that year, the Annual Official Guide to the Turf  from that did not include him, due to his skin color. In those days, most of the top jockeys were African American so it was a huge omission. In 1902 on Alan-a-Dale, he became the second jockey to win back-to-back runnings of the Derby after Isaac Murphy. This time, the Courier Journal called him as “black as an ace of spades.” Something interesting with Alan-a-Dale is that the horse was trained by a grandson of statesman Henry Clay, and Winkfield’s mother Victoria was a slave owned by Henry Clay.

The recession of that time really took its toll on racing, as attendance fell and racetracks folded, many white jockeys began replacing black jockeys on the horses, sometimes by force if necessary, and if a white jockey hurt a black one no one cared too much in those days, as was the case with any other white on black crime. There were even riots at racetracks near Chicago over black jockeys getting the mount over white jockeys. With Jim Crowe laws in full effect, and while receiving death threats from the Ku Klux Klan, Winkfield had enough and in 1904 decided to leave his home country for somewhere completely different… Russia.

Winkfield had finally reached the fame he had always dreamed of in Russia. The story goes that he was the personal jockey for Czar Nicholas, but in the Baltimore Afro-American from April 22, 1952 Winkfield says, “they say I rode for the Czar, but I never did. The Czar had a few little horses but I rode and trained for Montichev.” Regardless of the owners he rode for, his skin color had no impact on him getting mounts or the respect and admiration from horsemen and fans. During his time in Russia Winkfield won Russian Champion Jockey three times, the Russian Oaks five times, the Russian Derby four times, the Czar’s Purse three times, and the Warsaw Derby twice. He even won “Czarist Triple Crown”—the Moscow Derby, St. Petersburg Derby, and Warsaw Derby. All over Europe he was a first-call rider for such noble people as a German Baron and a Polish Prince. Not only did he earn 10% of all purses he won, but he was receiving 25,000 rubles a year. At one point was earning 100,000 rubles a year.

James Winkfield with his son George whose mother, Alexandra, was a Russian baroness.
James Winkfield with his son George whose mother, Alexandra, was a Russian baroness.

Finally, he was getting the recognition he deserved–not just as a top African-American jockey, but as an internationally renowned jockey of any color. Unfortunately for Winkfield, all good things must come to an end and so did his success in Russia with a resounding halt. In 1917 the Russian Revolution began and once again, he had to move yet again to a new country. But the trip was not an easy one, him and a few other trainers and owners took 260 horses to Poland. The journey was so treacherous and long–over one thousand miles over the Transylvanian Alps–that at points the group was so low on food that they had to resort to eating their own horses. All humans, and most horses, arrived safely but Winkfield did not end his journey in Poland, he continued on until he reached France.

In France he saw similar success as he did in Russia. He won such races as the now-Grand Prix de Saint-Cloud, the Grand Prix de Deauville, and the Prix Eugène Adam and was a celebrity among the French racing community. The Afro-American newspaper from July 13, 1923 commented, “whenever [Winkfield] showed himself on the thorofares, jubilant natives insisted on saluting him and drinking to his health.” Needless to say, his treatment here was very different than what he was getting back home. After about a decade in France he had 2,600  total wins in his career, and in 1930 retired from riding at the age of 48. Free from racism, he stayed in France on a farm near the Hippodrome de Maisons-Laffitte where he bred and trained racehorses. Unfortunately for Winkfield, he still could not catch a break when in 1940 the Nazi’s had seizes his farm and he had no choice but to move back to the United States where little had changed for him.

In Paris, Winkfield was a celebrity as he is seen here rubbing elbows with Bing Crosby
In Paris, Winkfield was a celebrity as he is seen here rubbing elbows with Bing Crosby

He spent his days in the USA at Aiken training center in South Carolina as well as at Bowie Racetrack in Maryland until 1953 when he returned back to Maisons-Laffitte. In 1961 he was invited to come back to Louisville, KY for a dinner at the Brown Hotel for the National Turf Writers convention. Unfortunately, he still found respect hard to come by in the USA as the hotel staff refused him entry until writers from Sports Illustrated confirmed that he was a guest.

He never came to the USA again, and passed away in France at the age of 93, a celebrity in Europe but almost forgotten in the United States.

In 2004, 30 years after his death he was elected to the National Museum of Racing and Hall of Fame in Saratoga Springs, NY.


The Kentucky Derby: How the Run for the Roses became America’s Premier Sporting Event by James C. Nicholson

2012 Kentucky Derby Media Guide


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