About Jimmy Winkfield
Thoroughbred jockey and horse trainer James Winkfield (April 12, c. 1880–1882–March 23, 1974) had an estimated net worth of $3 million. If not for history, Wink might have become the biggest racing phenomenon in America. Jimmy Winkfield, a jockey who won the Kentucky Derby twice, experienced racism, the Second World War, death threats, and exile throughout his life. He achieved fame, fortune, and true love while living the high life, but his two greatest loves were with horses and his exiled country, the United States.
Wink’s voyage takes him through tragedy, history, sprightliness, and traditional American inventiveness.
modest beginnings
Jimmy Winkfield, a horse racing enthusiast who was born in Chilesburg, Kentucky, in 1880, was inspired by the great black jockeys of the 1890s as he grew up. Ed Hotaling, author of Wink: The Incredible Life and Epic Journey of Jimmy Winkfield (McGraw-Hill; November 2004; Hardcover, $22.95), describes Jimmy Winkfield’s journey from shoe shine boy to stable hand to horse trainer. Wink finally had the opportunity to race at the age of sixteen. And he raced.
A Racist Victim:
He was one of only four jockeys to ever win the Kentucky Derby back-to-back in 1901 and 1902. The peak for black jockeys in America was also marked by Wink’s victories in the Derby. The great black jockeys were expelled from American racing around the turn of the century due to racism, enormous money, violence by white jockeys, threats from the Ku Klux Klan, and other factors. Jimmy Winkfield, who had no other options in his own America, purchased a steamer ticket for Europe, where horse racing remained the dominant sport and riders were well-known figures.
An Uproar in Russia:
Wink won the Czar’s Prize and the All-Russian Derby in Russia shortly after arrival, and he went on to win numerous other significant awards in Europe. He rose to prominence as the best rider in Czarist Russia’s sole national sport, taking home an unprecedented three riding titles. He married a Russian heiress, amassed enormous riches, and led a lavish lifestyle in Moscow. However, the whole aristocratic horse racing society was driven to Odessa on the Black Sea in the aftermath of the 1917 Russian Revolution.
Getting away to Paris:
In 1918, Wink and his colleagues jockeys, trainers, and owners drove 200 thoroughbreds across the Transylvanian Alps to Poland—a thousand-mile journey—even as the revolutionary army advanced into Odessa and set fire to the racecourse. To survive, they fed the horses horseflesh. Wink miraculously made it to Poland and then on to Paris, where he was feted alongside celebrities like Ernest Hemingway, Josephine Baker, and international monarchy.
Second World War:
He began working with horses in the grounds of his estate outside of Paris by 1940. Unfortunately, Wink’s life and livelihood would once more be affected by history. France was about to be taken over by the Nazis. Wink used a pitchfork to defend himself when German forces seized his land and confronted him at his own stables. Wink was once more compelled to leave because of a catastrophic disaster.
Returning Home at Last:
Wink made one more trip back to the country in 1961 after living abroad for decades after being invited as a two-time winner to a Kentucky Derby luncheon. However, when he and his daughter arrived to Louisville’s famed Brown Hotel, they were informed that they couldn’t enter through the front entrance. After a protracted wait, they were finally permitted entry, but everyone at the banquet ignored them. save for a former rival. Even though he hadn’t seen Jimmy in sixty years—during their derby days—a magnificent white jockey named Roscoe Goose came up, introduced himself, and sat down next to him. The Kentucky Derby the next day is where the book’s final public image of Jimmy was captured. He was seated next to his former competitor Roscoe; they were both wearing suits and hats, smoking cigars, grinning, and regaling reporters with tales. Wink had once more outpaced racism.
This is the remarkable, real, and almost unbelieveable tale of a magnificent guy and athlete who demonstrated his prowess as one of the finest jockeys in history in at least 10 different nations. He passed away at the age of 94 at his beautiful home and training facility outside of Paris, always yearning for the Kentucky bluegrass of his youth. Jimmy Winkfield’s wealth was $3 million when he passed away in 1974.
