History is a living organism, not necessarily a completely accurate or fair account of what really took place, but rather a feint recollection of what’s been selectively remembered or inadvertently preserved. One of the most forgotten components of American sports history is the collective accomplishments of the black horse jockey, namely their excellence and early dominance of America’s first national sport – and its crowning event, the Kentucky Derby.
Born in 1882, in Kentucky, Winkfield was a sharecropper’s son. By the time he was ten he did not have to look far to see that small black boys from the Bluegrass state could grow up and make a fine living riding racehorses. As Joe Drape, author of Black Maestro, The Epic Life of an American Legend, wrote of Winkfield’s early days:
“Jimmy has chosen the one milieu where black men could achieve some status, if not exactly flourish. In the South, no one denied they had a gift for horses, a reputation established when they where slaves on plantations, and wrapped in myth, mystery, and marvel.”
In the early 1890’s, the racetrack turf was one of only two places in the South where men where viewed to be created equal. The other: under the turf six feet below. Horse racing then was a tough sport for tough men, noted for its outlaw tracks and characters, unadulterated gambling and race fixing, general carousing and chicanery, mob violence and protectionism, and corrupt political bullying and bossism.
Winkfield loved, adored, and respected the horses he rode, tending to their needs with utmost compassion and kindness. As a jockey he was a natural rider who knew the ins and outs of every horse he rode with staggering precision and meticulous singularity. He knew how to cure what ailed the animals, and somehow he could turn even the most sluggish ones into champions.
The U.S. Supreme Court decision in Plessy v. Ferguson made black riders an endangered species in America, upholding the constitutionality of the world Winkfield had always known. Handed down in 1896 the decision legalized public segregation laws passed in 1890 by the Louisiana state legislature, stating that as long as trains offered “separate but equal” accommodations for black and white passengers, there was no reason they needed to sit together.
In 1901, despite increased aggression directed at him from white competitors, Winkfield had his best year ever, winning 161 races from New Orleans, Memphis, Chicago, and the Kentucky Derby aboard His Eminence.
He won the Kentucky again in 1902, remaining the last black jockey to win America’s most famous race, and one of only four of any color to capture the Derby in consecutive years.
After being completely marginalized by the growing intolerance for black riders, Winkfield fled to Russia, where no one asked him about his skin color, or treated him any different than any other horseman.
Russia’s well-heeled equestrian community was fascinated by his riding techniques, his crouch, how he positioned his knees to slow or speed up a horse, how he crossed the reins in a stretch drive to shake up a horse, how he could unleash a come-from-behind run. It was in Moscow that Winkfield learned that his new nickname “Black Maestro” was bestowed on him purely as a term of endearment.
Winkfield dominated the home grown jockeys, so much so that he was eventually chased from Russia. He loved his adopted home, but the tumultuous empire – in the throes of the Russian Revolution and the political murders of Czar Nicholas II and family – resented him for the misdeed of winning too much. In 1919, as Bolshevik cannon fire roared above, the already epic life turned into an odyssey, described crisply by Drape:
“With a ragtag band of Russian nobility and Polish soldiers, the son of a black sharecropper from Chilesburg, Kentucky, was entrusted with saving more than 250 of the most royal but fragile horses of Csarist Russia. They trekked 1,100 miles from Odessa to Warsaw for nearly three months amid the bloodiest part of the Russian Revolution, surviving gunfire and starvation.”
Eventually, Winkfield started a new life in the French countryside, finding success as a jockey and then later as a trainer. In 1941, Nazi troops requisitioned his estate and stables, and he had no other choice but to return to America and the racial restrictions of the Jim Crow South.
At age 66, he found a job in New York City breaking rocks for public works projects. He was saved from this indefinite sentence to hard labor, by his son, Robert, who found him a job as a trainer in South Carolina, returning Winkfield to the horses and the Southern rhythms of his childhood. With money earned from gambling on his own horses, Winkfield returned to France, where, in 1974, he died in a remote horse town.
In the cemetery at Maisons-Lafitte, Winkfield’s tombstone is simply marked. It says “Mockba” at its foot, the Russian word for Moscow, the place where the Black Maestro – one of the most dominant athletes of his sport – was best regarded when he was there and most remembered after he was no longer alive.
