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Jimmy Winkfield: the American jockey who escaped the Bolsheviks and Nazis

Nicholas Godfrey with one of the most fascinating untold US sports stories

Jimmy Winkfield: probably best known as the last black jockey to win the Kentucky Derby
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Published in the Racing Post on February 6, 2015

The most dramatic episode in a truly remarkable life came when Jimmy Winkfield, a dual Kentucky Derby-winning jockey exiled from his native land, played an integral role in leading a ragtag band of Russian nobility and Polish soldiers on a miraculous 1,100-mile journey to save more than 250 thoroughbreds left in crumbling Tsarist Russia.

The son of a Kentucky sharecropper, Winkfield is probably best known as the last black jockey to win the Kentucky Derby before African-Americans virtually disappeared from a sport they had dominated during its earliest years.

Jim Crow segregation laws, dangerous rough riding by their white counterparts, dwindling opportunities amid anti-gambling legislation and mass migration to urban centres were among the primary reasons black riders dropped out of sight in the first few years of the 20th century – soon after Winkfield's rapid ascent to fame culminated in his becoming only the second jockey to ride back-to-back winners of the Kentucky Derby on His Eminence and Alan-A-Dale in 1901 and 1902. The legendary Isaac Murphy, also black, was the first.

But that is only part of the charismatic Winkfield's amazing story, and an early part at that, for this was an extraordinary life lived more in Europe than his native America.

Forced to leave the States through a mixture of hard times, hubris and inherent racism, Winkfield rode big-race winners in Germany and became a celebrity in Poland and Russia, living in Moscow's finest hotel and eating caviar for breakfast.

Again, though, that wasn't the half of it. After his sensational horseback escape from Russia he began a new life in Paris – and, 20 years later, after setting up as a trainer at Maisons-Laffitte, he was again forced to flee, this time from the Nazis.

The incredible life of Jimmy Winkfield

Name James 'Jimmy' Winkfield 
Born April 12, 1882 in Chilesburg, Kentucky 
Died March 23, 1974 in Paris, aged 91 
Synopsis Last great black American jockey, a dual Kentucky Derby-winning rider exiled from his homeland, led 262 racehorses on an epic 1,100-mile, three-month journey in 1919 to escape Bolsheviks after the Russian Revolution. 
Afterwards Winkfield's riding career continued in Paris until he retired, aged 48, in 1930; subsequent training career ended when the Nazis requisitioned his Maisons-Laffitte stable and forced Winkfield to flee once more, this time back to the US. He eventually returned to France and re-established his stable with his son Robert in Paris, where he died in 1974, by which time his incredible story had finally gained a degree of recognition at home. But he still had to wait another 30 years before he was inducted.

Strapped for cash on his return to his native country, America's last great black jockey could be found manning a jackhammer on the sidewalks of Queen's, New York, before another turn at the racing game and a final return to France with his third wife Lydia and son Robert.

Things may have been very much black and white in Winkfield's time, but his existence was seldom less than technicolor. He was banned for a year after his first ride aged 16 ended in a four-horse pile-up; his left eye was crossed after partaking of some bad moonshine in a drinking den during his riding days in Chicago; and he was shot in the elbow by one of his many mistresses in his Paris stable.

Winkfield had three wives – a black Kentucky girl, the daughter of a White Russian soldier and a Russian baroness – and he treated them all badly.

"He loved them all and did wrong by all of them," says his biographer Joe Drape. "He divorced the first one, abandoned the second and humiliated the third."

Yet if Winkfield's story was astonishing, for several decades it was almost totally ignored in America, where segregation reigned for so much of his life. "This may be the most fascinating untold sports story in American history," suggested Charles Osgood on CBS News a few years ago.

A Sports Illustrated interview in 1961 had started the rehabilitation process but when the magazine invited Winkfield to a function at Louisville's Brown Hotel during the week of the Kentucky Derby he was told he was not allowed to enter via the front door owing to the colour of his skin.

When he died in 1974 he was granted an obituary in the New York Times. "Only turf historians, or perhaps those who heard stories told by their grandfathers, would have recognized Winkfield's name in the United States this decade," said writer Gerald Eskenazi.

Winkfield's tale is not untold anymore. Two worthy biographies have been published; there's a stakes race named after him at Aqueduct, and he was inducted into the US Hall of Fame in 2004. By then Winkfield was considered a bona fide racing legend, and his exploits as a latter day Hannibal leading his equine caravan to safety had become the stuff of racing folklore.

Top jockey Jimmy Winkfield wins a second consecutive Kentucky Derby on Alan-A-Dale

Winkfield's daughter once suggested her father had ended up in Russia owing to the attentions of the Ku Klux Klan but the jockey himself evinced another reason when he spoke to Sports Illustrated.

"I left because I got too smart for my pants," he chuckled, recalling how he had been blackballed after breaking a contract at Saratoga.

His rides dwindled and in 1904, in what was to become a decades-long odyssey, Winkfield boarded a steamer to cross the Atlantic and join the exodus of US jockeys to Europe, where Tod Sloan had revolutionised race-riding in Britain.

'Wink', as he was known, was headed for the richly endowed Eastern European circuit, based around lavish hippodromes in Warsaw, Moscow and St Petersburg. Several fellow American riders had found an unlikely home in this part of the world but none matched the success of Winkfield, who became revered as the 'Black Maestro' in Tsarist Russia.

Winkfield thrived on a series of lucrative contracts: he was Russian champion jockey three times, bagging a succession of major prizes including five Russian Oaks, four All-Russian Derbys and two Warsaw Derbys.

"For us Russian horsemen in the days before the revolution, the name Winkfield was like Shoemaker, Arcaro and Longden combined in one," a former captain in the Tsar's army wrote in a letter to Sports Illustrated after the 1961 article.

The outbreak of the First World War barely touched the Moscow-based jockey, who was earning an estimated 100,000 roubles a year thanks to a contract with Armenian oil magnate Leon Mantacheff. Winkfield was living in a suite at the palatial National Hotel with his own (white) valet Vassily, and enjoying a prominent role in Muscovite society. "If living well was the best revenge, Winkfield had plenty of it," suggests writer Ed Hotaling.

As a star performer in one of the nobility's favourite pastimes, Winkfield had fared well in Russia. "Before the revolution that was a good country and I never had to pay no income tax," he said. "There was no prejudice in Russia, not a bit. I would have stayed but for the revolution."

Others lower down the food chain were not always quite so fortunate, and Lenin's Bolsheviks were never likely to look kindly on a Tsarist pursuit like horseracing.

After the twin revolutions of 1917 the writing was on the wall for the Moscow Jockey Club, which undertook a piecemeal evacuation 700 miles south to the Black Sea resort of Odessa, a Tsarist stronghold destined to become the last refuge of Russian racing.

Winkfield got a job riding for a Polish officer – Polish horses had been sent there in 1915 to escape the war – leaving his second wife Alexandra and six-year-old son George in Moscow, figuring his absence would be only temporary. He never went back.

Racing continued without a hitch in Odessa through both 1917 and 1918 when the Odessa Derby – a de facto All-Russian Derby because there were no active racehorses anywhere else – was won by Horoscope, who had been transported by the Tsar's stud manager after he fled Moscow and the Bolshevik takeover.

Time, though, was running out for Odessa, which had become a sort of refugee camp for the rich and titled as Tsar Nicholas II's empire lay in ruins with Russia little more than one vast battleground.

The Tsar, his wife Alexandra and five children were executed on July 18, 1918; the continued existence of Odessa outside Bolshevik control, supposedly protected by a French buffer force, was an eyesore for the new regime. When the Bolsheviks reached the outskirts of the city in the first week of April 1919 desperate measures were called for.

A hazardous escape plan

Winkfield, then 39, readied himself for a hasty withdrawal. "I got to thinking this ain't no longer a fit place for a small coloured man from Chilesburg, Kentucky, to be," he recalled.

Frederick Jurjevich, the remarkable Polish horseman who had overseen the Odessa racing community, had an escape plan but it was hazardous indeed, involving an evacuation of men, women and children – plus the not insignificant detail of 262 thoroughbreds.

Winkfield, who said he was damned if he was going to leave the horses "to be eaten by the Reds", was to be his chief lieutenant on a perilous 1,100-mile journey across the post-war wasteland to safety in Poland.

The route they were to take was hardly direct as they sought to avoid the marauding Red Army, whose reaction to meeting a band of aristocratic horseracing exiles might not have been entirely positive.

The sound of cannon fire on the outskirts of Odessa was enough for the plan to be put into practice. After a night in which Winkfield and his fellow jockeys, trainers, owners and grooms had worked silently at the stables readying the convoy, they set out at 6am with Jurjevich riding the 1917 Odessa Derby winner Leige.

They were initially headed on a 300-mile detour towards Bucharest, where the women and children were to be sent ahead on a train to Warsaw. The scene as they escaped from Odessa is vividly brought to life by Hotaling, who says: "Winkfield and his cohorts passed burning depots on the port road, walking the herd through smoke and soot as the cannon fire continued in town ... [they] picked their way past corpses of other horses and broken military vehicles."

Food soon became scarce for both humans and horses: Winkfield and his companions had to beg for what they could in villages where the locals sometimes opened fire on them, scared they were Bolsheviks come to plunder. In Romania they were frequently turned away in the belief they were gypsies.

Then there was another issue: the Poles, brilliant horsemen, were also good Catholics. "Once we came upon this cow," recalled Winkfield. "But it was Lent and no-one would eat her! We drove her along for 20, 30 miles, trying to get her to Easter. We finally swapped her for a pig and ate him on Easter Sunday!"

Exhausted and starving, this monster wagon train made it intact to Bucharest where the women and children duly boarded their train. But if the load was lightened there was still 800 miles left for Winkfield's horsemen and their malnourished thoroughbreds, who continued along the Transylvanian Alps north to the Dniester River into the Carpathians.

Without hay and grain the horses had to survive on little more than green grass; not all of them survived, and those who perished were butchered and eaten.

After a particularly hair-raising episode as they crossed a rickety wooden-plank bridge high above a ravine – led by none other than the Tsar's horse Horoscope and his Polish rider, the fearless Jaworski – Winkfield's bedraggled convoy reached Polish soil and the town of Czernowitz before covering the final miles in battle formation as the border was under attack from the Red Army.

Finally, three months after they had left Odessa, they reached the old Mosotowski racecourse in Warsaw – the same racecourse at which Winkfield had launched his international career with his Warsaw Derby victory soon after leaving the States 15 years earlier.

The equine exodus, which has gone down in Polish history as 'The Odyssey' was over. That no fewer than 252 thoroughbreds survived such an arduous journey was little short of a miracle; some of them even featured on the racecard when racing resumed in Warsaw a few weeks later.

Winkfield did not stay in Poland as he soon rejoined his former retainer Mantacheff in Paris for the next stage in an epic career. He was later to marry a daughter of the Russian aristocracy, get shot by a mistress, win big races in France, ride in the St Leger (finished fourth on Bahadur, his only ride in Britain) and set up a training operation at Maisons-Laffitte – only to have his stables taken over by the Nazis.

But that's another story. The incredible life of Jimmy Winkfield was full of them.

Taking the smart route to a second Kentucky Derby success

Jimmy Winkfield's second Kentucky Derby triumph in 1902 demonstrated the rider's nous – and not just in the race itself. Winkfield had been engaged to ride for Major Thomas Clay McDowell, a powerful owner-breeder who had a pair of Derby contenders in Alan-A-Dale, a scrawny looker with dodgy legs, and a rather more impressive individual in The Rival.

Winkfield was work-rider for both horses and he reckoned Alan-A-Dale was by some measure the better animal; the problem was McDowell had also engaged top east-coast rider Nash Turner, and Winkfield knew the white boy would be given first choice.

Winkfield therefore went to great lengths to disguise Alan-A-Dale’s true merit, restraining the chestnut as best he could in morning workouts while allowing The Rival to use his tremendous stride at full pelt.

Allied to his looks, The Rival's superior clockings were enough for Turner to select him, leaving Winkfield clear to partner the horse he wanted. Street smarts were also required in the race.

Alan-A-Dale had established a four-length lead into the backstretch but the margin was down to just a length as they entered the far turn, where Winkfield had to do something to maintain any advantage.

Local knowledge was to prove crucial; Winkfield knew the Churchill Downs ground crew habitually pushed heavy sand to the outside of the track, leaving a faster strip inside.

When leading fancy Abe Frank began to launch a serious challenge, Winkfield fanned him out on to the slower patch before yanking Alan-A-Dale back to the rail and forcing The Rival and Inventor to swing wide outside him as well, beaching the pair for a stride or two. Alan-A-Dale won by a nose in a slow time. "Well, I tell you why it was slow," said the jockey. "I was riding four horses!"

Sources: Around the World in 80 Years – Sports Illustrated article (1961) by Roy Terrell; Black Maestro – The Epic Life of an American Legend (2006) by Joe Drape; The Great Black Jockeys: The Lives and Times of the Men who Dominated America's First National Sport (1999) by Edward Hotaling; Wink: The Incredible Life and Epic Journey of Jimmy Winkfield (2005) by Edward Hotaling. 

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Winkfield and his companions had to beg for what they could in villages where the locals sometimes opened fire on them, scared they were Bolsheviks
E.W. Terms