Chronicles of The Black Jockeys Volume VII: He Won Back-To-Back Derbies, Fled The Bolsheviks in Russia; Fled The Nazis in France; Only To Be Denied Entry in America - to the Louisville Derby Function Being Held In His Honor

With the opening of horseracing season with the running of the 139th running of the Kentucky
wink2Derby and the approach of Preakness and Belmont, we have presented a series of some six volumes in the history of the black jockeys, who were pioneers in American racing from the dawn of horseracing before the American Revolution, through the Civil War, and up to the eve of the 20th century, after which they essentially disappeared from the sport.  We have chronicled the achievements of the early slave jockeys such as Cornelius, Charles Stewart, Cato, Dick, Albert, Chisholm, Sewell, Simon, and Austin Curtis, and the latter celebrities of the late 1800s including Oliver Lewis, Isaac Lewis, William “Billie” Walker, Isaac Murphy, Erskine Henderson, Alonzo “Lonnie” Clayton, Shelby “Pike” Barnes, Babe Hurd, Monk Overton, Tommy Britton, Tiny Williams, George “Spider” Anderson, Willie Simms, James “Soup” Perkins, and Tony Hamilton

The last great African American jockey would not see the stardom of an Isaac Murphy here in America, as his American riding period was relatively short.  During his time in America, however, he made his mark by capturing back-to-back victory in the Kentucky Derby, matching one of Murphy's records, but this jockey would have the distinction of being the first and the last African American jockey to win a Kentucky Derby in the 20th century.  As the 20th century evolved without much presence of African Americans in the sport and with a seeming continual trend into 21st century, he remains the last African American winner of the most important horserace in the country.

James “Wink” Winkfield

Wink7Jimmy “Wink” Winkfield was the last great African American jockey.  Early success in America would see him off to Europe to be feted in imperial Russia during the reign of the last czar, Emperor Nicholas II, where Wink would also bear witness to the waning days of the Romanoff dynasty.  In the face of the approaching Bolsheviks, he would escape from Odessa, leading a colony of horses, jockeys, women, and children to Romania, from where he, his men, and the horses, would reach Warsaw, Poland by traversing the Transylvanian Alps and crossing Hungary and Czechoslovakia in a two month journey to finally reunite in Warsaw Poland.  In Warsaw, he saw a stardom that would be later duplicated in Austria and in Germany, leading up to an eventual life in Paris at its heydays.  Like the other African American jockeys, much of Jimmy Winkfield’s achievements remain but another example of illegible footnotes in the annals of American history.

As an example of young aspirations being fed by the presence of tangible role models, Jimmy Winkfield grew up in an era when black jockeys claimed multiple victories at the Kentucky Derby.  When Winkfield was ten, Alonzo “Lonnie” Clayton won the Derby.  When he was thirteen, James “Soup” Perkins won the Derby.  When he was fourteen, Willie Simms had claimed his first victory, to be repeated when Wink was sixteen.  By the time he was nineteen, it was Wink's turn at the winners’ circle, and he claimed his first Kentucky Derby victory.

In recounting his story many years later to Sports Illustrated writer Roy Terrell, Winkfield said that in 1896 when Simms won his first Derby, “I was going to school at nights and driving a carriage for some white folks during the day.  Saturday we would all go to the racetrack.  I used to play marbles with the stable hands between the races, and I got to know the people there.  One day in the spring of ’97, a man offered me a job at Latonia (Kentucky) for eight dollars a month and board.  I was rich.  I galloped (exercised) an old mare that year that won five races, and each time she win, the owner gave me $5 and the jockey $5.  That horse ran a hell of a race.  The next spring, Bub May (stable owner) hired me for ten dollars a month and board.  His daddy was mayor of Lexington, and in the summer of ’98, they took some horses to Chicago, to Hawthorne racetrack.  That’s where I rode my first race.” 

Winkfield’s first race was an abject failure.  He ran across fellow jockeys and caused a major pile up on the tracks.  He said that when the stewards took him off the ground and asked him where was he riding before, he responded, “I jus rode.”  “Ain’t you never rode before boy?” one asked.  “'No sir’ I said.  So they looked at one another for a while, and they just put me afoot for a year.”

After waiting out his year, he got to mount the horse ‘Evan Stock’ in a race at Hawthorne, to be followed by thirty-nine victories at an Indiana racetrack.  That earned him a twenty-five dollar a month contract with Bub May, who then entered him in races at the New Orleans Fairgrounds.  Wink soon rose to being the number three jockey there by 1900.  He was then hired out by his stable to ride in the 1900 Kentucky Derby.  Regarding the crowd at the Derby back then, Wink said, “They would walk twenty miles to get there and then couldn’t find a place to sleep.”  He placed third in that Derby with twenty-five dollars to his pocket and three hundred dollars to the owner of the horse.   “Usually I did not get anything extra unless I win, and then only five or ten dollars.  It still wasn’t much money but it would keep getting better.”

Jockey Race War

According to Edward Hotaling, author of The Great Black Jockeys, “things were getting so good for Jimmy Winkfield and other black jockeys that it led to a race war that August on a Chicago racetrack."  “A race War in between the jockeys at the local tracks,” said the headline of The Thoroughbred Record.   “Jealous because of the success of so many of the colored riders, white boys have taken desperate measures to put their rivals out of business.”  The Record reported that the war had led to several incidents at Chicago’s Harlem track.  It went on, “Winkfield, one of the most successful of the colored boys riding at Harlem, was crowded against the fence, bruising his legs.  Horse and rider escaped luckily at that.”  But as it turned out, Winkfield’s horse had incurred a couple of cracked ribs during this racist attack.

So routine did these terror tactics become, that the black jockeys had to fight back.  The Thoroughbred Record continued, “The Colored lads, becoming convinced that they were badly used, retaliated and the next day, took a hand in the rough tactics.  The officials who are aware of the jealousy, have done all they can to adjust matters and keep peace among the boys but have not yet succeeded in preventing accidents.”  Though this turned out to be relatively minor in the larger scheme of things, these racist attacks on the racetrack portended what was to become one of the key weapons used to drive the black jockeys out of horseracing in the 20th century.  For his part, when he was ganged upon and forced into the fence, Jimmy Winkfield’s response was simply to keep on riding to finish the race.  

1901 Kentucky Derby

In 1901 Bub May sold Winkfield’s contract to Patrick Dunne, and Winkfield immediately shot up to one of the top riders in the country with 161 wins.  He entered the Kentucky Derby that year on the horse ‘His Eminence’ (son of legendary horse Falsetto which took Ike Murphy to notoriety).  Said Winkfield, “I got him away in the front and stayed there.  Was nothing to do it.”  Jimmy Winkfield had won his first Kentucky Derby in 1901.  For this win, he got a five hundred dollar bonus.

1902 Kentucky Derby

The next year, Winkfield was tapped to ride in the Derby for stable owner Thomas Clay McDowell, who was putting up two horses, ‘The Rival’ and ‘Alan-a-Dale,’ in the race.  Only a few years before, Winkfield was the exercise boy who gave the horses their workouts and so he knew that Alan-a-Dale was the faster of the two.  But to everyone else, Alan-a-Dale was known mostly for having weak legs.  Winkfield’s competition for the better horse was a top white rider from the North, Nash Turner.  So Jimmy had to be inventive in order to get the horse he wanted to ride.  Later, he would recall that, “Nash was a good jockey, pretty famous by then, and he was a white boy, so he was going to get his pick (of the horses).” 

WinkFor a month, I pulled Alan-a-Dale in workouts.  I never let him go better than 2:11 for a mile and a quarter, and all the time, I galloped The Rival at about 2:09.  So when Nash came down on the morning of the race, naturally he picked The Rival.”  Once they were off racing, it became a tactical race in which Jimmy had to eliminate the strongest competition on the track with subtle tactics such as taking them wide and into the protective layer of sand at the outer edges of the track.  Jimmy knew the track very well, having worked there as an exercise boy, and he knew the outer edges had sand that would slow some of the faster horses.  Winkfield also knew Alan-a-Dale’s weak legs might have given out had he pushed her too hard, so to win, he took his competitors through the path of most resistance.  The tactic worked, and it slowed The Rival and others such as Tiny Williams on ‘Inventor’, ‘dead in their tracks’ (another sport term originating in horseracing).  

Jimmy Winkfield would tie one of Isaac Murphy’s records in 1902 by winning back-to-back Kentucky Derbies.  Alan-a-Dale’s leg lived up to its weak reputation and the horse unfortunately limped from the finishing gate and would never race again.  “For a long time, people keep asking me how come the second half of that race went so slow.  Well, I tell you why it was slow.  I was riding four horses,” said Jimmy Winkfield to Sport’s Illustrated's Roy Terrell.

Winkfield’s rival Nash Turner gave another, though not very credible version of the events.  He claimed he was just a decoy.  But a white rider, especially one of Nash Turner’s stature, would never have been used as a decoy in racing and would always get his preferred mount of the better horses.  Said Turner, “Switching me to ride The Rival caused Mr. McDowell to win the Derby.  I was put on the worse horse so as to confuse the other boys.”  But it was Turner who had in fact chosen to ride The Rival, primarily because Winkfield had tricked them in practices by holding back Alan-a-Dale to give The Rival the better timing.  Turner then claimed to have held back most of race and that the other main competitors stayed with him, “thinking I had something up my sleeve.  When I made my move on The Rival, after straightening away for home, they realized that the horse was all out, and the other boys set sail for Alan-a-Dale but Winkfield had gotten too much of a lead on them.  If I had been on Alan-a-Dale, the result might have been different.  Coburn (Monk) and Williams (Tiny) would have chased me hard all the way.”

According to Edward Hotaling, Winkfield was paid a thousand dollars for winning that Derby.  White rider Nash Turner was also paid a thousand dollars, for placing third.

1903 Kentucky Derby

Wink5By 1903, Jimmy Winkfield had become a star with aspirations and expectations of matching Isaac Murphy’s three wins at the Kentucky Derby.  The Louisville Courier-Journal’s ‘complimentary’ headline had written it this way, “A colored boy but one of the great race riders of the world.”  Winkfield mounted the heavy favorite, ‘Early.’  The starter for the race Jake Holtman was considered to have had the worse job in horseracing since the crowd was often abusive when the horses did not get off to a proper start, and the race would sometimes be subjected to several restarts... over and over and over again.  This race was especially nerve wrecking for the starter as machines were being used for the first time at the starting line.  The machines were rather primitive contraptions that caused even more confusion, with elastic tapes that would be broken when the horses take off.  The horse that broke early would be called back and the tapes retied for the next start. 

I want you boys to stand up to the barrier and not break until I give you the signal,” yelled Holtman.

I don’t intend to take any monkey business, and the first one of you that gets gay will be set down for the meeting.” 

After several false starts, Winkfield turned his horse a little bit, enough that, “a beautiful start was spoiled,” according to The Louisville Courier-Journal.  

You little nigger!” yelled Holtman. 

Who told you that you knew how to ride?  You are not down at New Orleans now, and so come on and get in line.” 

Remarkably, Holtman had racially admonished the two-time Derby winner and reigning champion with reference to his early days making a name for himself in New Orleans, as if Winkfield had never ridden in the Kentucky Derby before.  At the finish line, Winkfield and horse were not able to pull it off.  He had been dealt defeat of less than a length by jockey Harry Booker, riding the ‘Judge Himes’.  The headlines were not forgiving.  “Ill-Timed Ride by Winkfield, the Great Jockey, Responsible for the Result.”  The Courier-Journal interviewed the winner, white jockey Harry Booker, after the race.  He was from of all places, Chicago, where white jockeys had earlier declared war on the black jockeys and had previously engineered the attack on Winfield and horse on the racetrack.  As he caught ‘Early’ in the stretch, Harry Booker said, “Winkfield turned around at me and laughed.  It was then that I was sure I did not have a chance.  That nigger, I was sure, was trying to make a sucker out of me.  I thought he wanted me to come up to him so he could draw away.  I knew that I had all others to beat off, so I just went on.  I passed ‘Early.’  ‘I have got the nigger beat’ I said to myself, and then I went to bat.  Winkfield could not catch me.  That’s the whole story.”

As Hotaling points out, in the same headline that trumpeted “The Great Jockey Winkfield,” Jimmy Winkfield was peppered with racist slurs by both the starter of the race and the winning jockey.  Such a favorite of the Kentucky crowd had he become that of the crowd, which included betters who had placed large sums on a Winkfield win, one reporter said, “The tremendous crowd greeted the victor like the sad thousands watched the funeral train of the assassinated President McKinley as it wended its way from the Capitol to Canton.  Near the roof of the stand there were sobs and sighs and tears.  Below, on the lawn, the warm blood froze in the veins of men who had bet their thousands on Early.”   As for Winkfield, he blamed himself.  “I made my run too soon.   I wanted to win for the bosses, and had I followed instructions, I would have won.”  Years later, Winkfield’s reflection on the race showed his high ethical approach to racing then:  “When that boy came to me at the sixteenth pole, I could have found him a little; I was such a favorite they’d never have disqualified me, not in that race, but I let him go and he won.”

1903 would be Jimmy Winkfield’s last Kentucky Derby.  He was noted to have never “finished out of the money” in a Derby race, having placed third in his first Derby, winning his second and third, and placing second in his fourth and last Derby.


jimmy-winkfield-story-topThat year also saw Winkfield rank 14th overall jockey in the country.  He then went up to Sheepshead Bay in Brooklyn to tackle the big stakes at the Futurity, which would see his profile rise on the national stage.  Futurity was then the richest race in the country with a purse more than seven times that of the Derby.  Winkfield at first decided to ride ‘Minute Man’ for owner John Madden against the favorite ‘High Ball’ which was owned by Winkfields’ longtime former collaborator, Bub May.  But May then approached his old jockey with a proposal.  “He came to me and offered me $3,000 to ride his colt,” Winkfield later recalled.  “’I am riding for Madden,’ I told him.”  “’Well,’ he said, ‘there’s $3,000 here if you change your mind.’”  “So I changed my mind.  At the last minute I told Mr. Madden I ‘d gotten mixed up, that I’d already promised Bub May I’d ride for him.”  This was considered ‘contract jumping’ in horseracing, which had previously been grounds for suspension if proven or even suspected.  “Course I didn’t fool Madden (for) a minute.  But I rode High Ball and we got left at the post and finished sixth.  The Minute Man was third.”

The winner of that Futurity was another horse, ‘Hamburg Belle’ and Madden was furious.  He believed his horse could have won with Jimmy Winkfield atop.  “After the race, Madden, he came up to me and said, ‘Winkfield, I don’t like to be double-crossed.  If you’re not going to ride my horses, you’re not going to ride for anybody.’”  At that time, John Madden was not the type of man that any jockey – black or white – would want against them.  He was an influential man from the North who advised and consulted for giants like W.C. Whitney who had by then taken over Saratoga, and Madden had also opened and operated a big stable in Kentucky.  So when he told Wink that he would not ride for anyone, if not for him, Madden was in a position to enforce that.  Jimmy Winkfield saw his mounts drop from 391 in 1902 to 223 in 1903.  He saw it coming and decided not to sit around and wait for it to happen.

The Ku Klux Klan

Many years later, Winkfield’s daughter revealed that the Ku Klux Klan had threatened her father before his departure from the United States.  Edward Hotaling states that the Ku Klux Klan threat was not the motive that Sports Illustrated interviewer Roy Terrell claimed Winkfield had given for his departure from America during their interview.  Terrell said that if Jimmy Winkfield had not jumped John Madden’s contract, he might have not left for Europe.  Terrell quoted Jimmy as saying, “I left because I had gotten too smart from my part.”  

But it is not hard to imagine Winkfield being threatened by the Ku Klux Klan or other sources of racist violence, on or off the racetracks.  At the dawn of the 20th century, race riots instigated by white vigilantes were taking hold on the country.  Southern states were busy putting all forms of segregation statutes on the books in areas of public transportation, health, facilities, and education, as well as anti miscegenation laws.  These were to be formally enforced by the courts and local authorities, and informally enforced by groups such as the Ku Klux Klan.  It was therefore hard to envision the free movement and safety of black athletes who were at the top of their game, making large sums of money, and enjoying a celebrated lifestyle, in the America of the early 1900s.  W.E.B. Du BoisThe Souls of Black Folk, published around that time in 1903, had said it all.  The problem of the twentieth century, especially in America, was “the color line.”

To Russia With Love

Wink8So that winter, when I got a chance to go to Russia, I went…”  A stream of American jockeys, white and black, had been leaving America for Europe in those days, mainly due to their desires for prolonged careers in face weight restrictions in America, which shortened many careers.  Willie Simms had opened the door in the mid 1890s and though he did not stay in England, other Americans such as Tod Sloan had found great success in Europe.  In the case of Sloan, he had taken the same American Seat (‘negro couch’) to become a great star and famous playboy in England.  Others such as brothers Lester and John Rieff and Danny Maher went to England as well, while a shift to the continent saw jockeys such as Winnie O’Connor, America’s top jockey in 1901, and Joe Ransch who was the top jockey in 1902, leave America to ride in France.  At the end of 1904, O’Connor said, “I have had the best season I have ever had.. and I am greatly pleased at my treatment.  I shall never again ride a season in America.”  The Louisville Courier-Journal then remarked, “In former years, England was the Mecca for American riders, but the fate of the Rieff brothers has made a lot of the talent clear of Britain’s shores, and sunny France and icy Russia have been the spots most sought.”  A visiting Russian turf official remarked in 1904 that, “In all European countries, the scale of weights is higher than here, and this is especially true in Russia.”  

Jimmy Winkfield, however, never had a weight problem and it is likely that the attack on him in Chicago and the emerging reign of racist terror in America ultimately convinced him to look to Europe. 

Before getting permission to go to Europe, jockeys needed to secure a contract from the host country.  At the turn of the century, Lexington trainer Jack Keene was training horses in Poland and Russia for various stables.  Keene was an acquaintance of Winkfield’s, and the timing of Keene’s difficulties abroad worked to the advantage of Winkfield, who was seeking to leave.  A doping investigation in Moscow, (again, another sporting phenomenon with origins in horseracing) involving Keene and his best jockey, American Carroll Mitchell, resulted in both their suspension from racing.  Keene asked Winkfield to travel to Russia and take care of the riding and training operations until he, Keene, could join him.  Wink’s first stop was in Poland where Keene’s horses were being trained, and he went straight into doing what he knew best.  “They gave me a book so I could learn Polish… and I rode two winners on opening day.” 

As it would turn out, Keene, who had sent Wink to deal with his business until the heat (from the doping scandal) was off him, would not show up for many years.  Jimmy then started to work with and to ride for Armenian oil tycoon Michael Lazareff, who owned most of the horses in the Keene stable and who was the leading stable owner in Poland as well.  He worked for Lazareff’s northeast circuit – from Warsaw to Moscow to St Petersburg, and then back to Moscow.  “I went down to Moscow and won the Emperor’s Purse that year, worth about 50,000 rubles..  We really cleaned up,” said Winkfield.  According to Hotaling, Russian reports indicated that Lazareff made about 300,000 rubles in winnings that year, the bulk of which was won by Winkfield.  As a result, said a Russian correspondent, "Jimmy Winkfield has made many friends among the Russian sporting fraternity and the public always made him a betting favorite, even though he’d be riding a goat.”

In his first year of riding in Russia, Winkfield won the Russian National Championship in 1904.  Ironically, he won it from another American, white jockey Joe Pigott.  Winkfield also won all of the three big Russian Derbies – the Moscow, the Warsaw, and the St. Petersburg Derbies, described by Hotaling as a “kind of Czarist Triple Crown.”  Hotaling quotes a Russian commentator visiting America during that time as saying that the American jockeys, including Winkfield, “have earned salaries in Russian beyond their fondest hopes, considering their terms in the country was up.”

Back In America

The banner headline, “Yankee Jockeys Back in America,” in the December 1904 Louisville Courier-Journal read, “This is the time of the year when the American jockey who has been forced to go to foreign climes on account of his weight, comes sailing for home to remain for the holidays.”  Among them were Winkfield and another black jockey, James Gannon, who had previously been a star at the Harlem track in Chicago but who was also now working in Poland.  But Winkfield would not stay in America as he had already secured contracts to return to Russia and other parts of Europe where he would keep riding through the second decade of the twentieth century, outclassing and out-earning his white counterparts.

1909 – Russia, Germany, Austria

Jimmy Winkfield IWhile the sport was in the process of self-immolation America, especially in New York, Wink left his long time collaborator Michael Lazareff in Poland and went to Austria to ride for a Polish prince and then on to Germany to ride for a German baron.  In Germany, he won the ‘Grosser Preis von Baden,’ worth a hundred thousand marks, and he soon became a big factor in German betting operations (the odds).  He would later recount his story of riding for the baron in his Sports Illustrated piece with Roy Terrell.  One day Wink said he decided that he wanted to ride one of the baron’s colts that no one thought could run, so he talked to the baron about riding the colt.  “I was getting pretty famous over there by then, and the baron said no, if I ride him, the people would bet on me and loose their money.”  Finally the baron gave in and allowed Wink to ride the colt.  At the start, Jimmy was stuck on the difficult colt while the other horses were fifteen lengths up the track.  “Then we get to the stretch and I give him a cluck or two, and off we go.  He ran so fast the others never see us coming.  We win by eight lengths.”

Living Large 

Don’t get mad at racism in American or even at your forced exit for greener pastures.  Get ‘even’ by living large.  In 1913, Winkfield went back to Russia, this time to work with another Armenian, Leon Mantacheff, for a salary of twenty thousand rubles plus ten percent of all purses.  He took a suite at the National Hotel in Moscow (equivalent of the Waldorf-Astoria), hired a valet, and had caviar for breakfast each morning.  “I was at the top of a tree,” said Wink.  He had other American colleagues and friends in Russia, mostly white jockeys who would keep him abreast of what was happening back home in America.  The news he got was that as a result of the shut downs of racetracks across America, many white jockeys were fleeing in search of opportunities in Europe.  As for the black jockeys, Wink was told that they were a thing of the past.  American racing had gone from 314 racetracks to 25 by 1908, with most of the major venues at the center of racing in New York, legislated out of business.  While Winkfield was exploding on the European stage, his counterparts in America were struggling to find mounts.  His black counterparts were no longer a factor in American horseracing.

So well did he succeed in Russia with his new collaborator Montacheff, that he told Sports Illustrated, “We sure won a lot of races… I won 130 one year, riding only three times a week.”  If we allocate, say, six out of fifty two weeks for vacation or holidays (a rough guess), Winkfield’s winning percentage would be an astounding 94 percent.  It might have been even higher depending on the length of the racing season.  Jimmy “Wink” Winkfield, had indeed made the right decision to flee America.  As will be explained later, he was the Bricktop, the Eugene Bullard, the Josephine Baker, the Sydney Bechet, and the Henry Ossawa Tanner of horseracing.  They all had their Paris but Wink had his Russia, his Poland, his Austria, and his Germany, at a time when his fellow African Americans could not drink at a water fountain in Alabama, unless it was designated for blacks.  But Jimmy Winkfield too, would soon have his Paris as well.

Czar Nicholas II

Winkfield was living and racing in imperial Russia, with the last czar Nicholas II as its Head Of State.  He said he opted not to work for czar Nicholas II because the czar kept 25 percent of his winnings and gave the rest to the owner of the second horse.  According to the capitalist Wink, “He never paid his jockeys nothing.  Maybe 4,000 rubles, so I never rode for him.”  But the czar, with a passion for racing, was one of Winkfield’s biggest fans, who often showed up at the track to watch Wink race.  Of Russia, Wink said, “Before the revolution, that was a good country.  And I never had to pay no income tax.”  But the Bolsheviks would soon arrive and Jimmy Winkfield would soon be forced to flee the country in which he had accomplished so much and in which he had enjoyed such a good life.

Arrival of Bolsheviks

When the Communist Revolution came, Jimmy said the Russians were “like rabbits in the woods.  They did not know which way to go.”  As would be expected, the Bolsheviks allowed the tracks to stay open and paid little attention to the people there.  A revolution needs people on its side, and it would be unlikely to get the people on its side by closing down their beloved sport.  One of those involved in the sport, however, was an African American capitalist who was earning upwards of an equivalent hundred thousand dollars annually.  So this was Jimmy’s tactic for surviving, as he later recounted to writer Terrell:  “Nobody bothered us so long as we stayed dirty and wore old clothes.  But if we ever dressed up, they would have figured we were aristocrats.”  No doubt he had by then ditched both valet and hotel suite, and would have likely procured his morning caviar in underground markets and discretely consume.

Fleeing Russia

The Moscow Jockey Club soon ran out of money and they shipped all their horses to the Black Sea resort of Odessa.  Odessa was a natural haunt of the Russian aristocracy and had soon become a more dangerous place to be than Moscow.  With revolution troupes on the edge of the city in April 1919, Jimmy recalled telling himself, “This ain’t no longer a fit place for a small colored man from Chilesburg, Kentucky, to be.”  He assumed responsibility for moving the entire racing operations, inclusive of jockeys, women and children, along with some two hundred thoroughbreds.  Along with a Polish nobleman, the group headed south first towards Romania.  Jimmy said it was quite a trip.  Villagers often fired upon them thinking they were Bolshevik agitators.  Others would not give them food, thinking they were gypsies (a small black man, a sight never before seen by such villagers, might have certainly given cause to believe that they were indeed gypsies).  And then there was the issue of timing and cultural practices.  “Once…  we came upon this cow.  But it was Lent, and no one would eat her.  We drive her along for 20 or 30 miles, trying to get her to Easter.  We finally swapped her for a pig and ate him on Easter Sunday.”  In other words, Wink and his group had to run out 'Lent' in order to be able to consume a piece of meat in that Orthodox region of the world.

In the Romanian capital of Bucharest, they put the women and children on a train bound for the Polish capital of Warsaw, and then the men and horses were off again.  They took the horses across the Transylvanian Alps and through a patch of Hungary and Czechoslovakia.  Some of the horses starved to death on the trip.  Some others were eaten in order for the men to stay alive.  The journey from Odessa to Warsaw was a thousand miles and took two months travelling.  On arrival in the Polish capital, only 150 of the original 200 horses remained.  Winkfield said that none ever raced again and that they were all eaten that winter (consumption of horsemeat...  not a new phenomenon in Europe).  In Warsaw, Jimmy would resume riding again, including once before a vising American VIP named Herbert Hoover.

An African American in Paris

For those of you who are familiar with EalyMaysArtworks, you might have also imagined that at some point, the chronicle of this legacy would also culminate in the story of an African American legacy in Paris.  We did not disappoint.

1920s Paris

Wink41920 would see the arrival of the last great African American jockey in the city of lights where he finally had company.  1920 was twenty nine years after Winkfield's fellow African American, artist Henry Ossawa Tanner, had fled a racist America for France, in search of artistic acceptance, which he would finally receive, from inclusion at the Louvre, of all places.

1920 was the year after another African American, Corporal Eugene Jacques Bullard, recipient of France’s “Croix de guerre” and “Medaile Militaire”, was discharged from the French armed forces as a national hero of significant standing, having downed possibly two enemy aircraft while flying his Nieuport over Metz.  He would later become part owner and host of Le Grand Duc restaurant, where he entertained the likes of Ernest Hemingway, F. Scott Fitzgerald, Gloria Swanson, and England's Prince of Wales.  A young Langston Hughes also found work at Le Grand Duc, working as a bus boy under Bullard.  African American Eugene Bullard is the world's first black fighter pilot, having served France during World War I.

1920 was four years before legendary African American nightclub owner Bricktop (Ada Beatrice Queen Victoria Louise Virginia Smith) would set up her nightclub Chez Bricktop in Paris. It opened in 1924 and lasted until 1961.  She counted American royalties such as the Doris Duke and European royalties such the Duke and Duchess of Windsor as her friends.  She gave a young Mabel Mercer her start as a headliner at her club, and once threw writer John Steinbeck out of her club for "ungentlemanly behavior." (He regained her affection by sending a taxi full of roses the next day).  Bricktop has been called " of the most legendary and enduring figures of twentieth-century American cultural history."  Queen Ada started her reign in the Paris of the 1920s.

1920 was be five years before the arrival of jazzman Sydney Bechet, noted for having recorded before Louis Armstrong, as well as for being allowed into France a second time, even after a deportation from England as well as a previous deportation from France for injuring a passer-by in a shooting incident.  His first trip to France was the fall of 1925 as part of ‘La Revue nègre.’  French Existentialists would come to call him "Le Dieu" (The God).  So loved was he by the French that he was allowed back into the country in 1950. 

That same ship which arrived in France with Bechet and other members of La Revue nègre, would include none other than diva Josephine Baker, who was also part of the group.  Baker was the first African American female to star in a major motion picture, Zouzou, the first African American female to integrate an American concert hall, the first African American female to become a world-famous entertainer, the first American-born woman to receive French military honors the Croix de guerre and the Rosette de la Résistance, and the first to be made a Chevalier de la Légion d'honneur, which was presented by General Charles de Gaulle.  In death, her funeral at L'Église de la Madeleine, added another ‘first’ to her legacy: The first American woman of any race to receive full French military honors at her funeral.

So when Jimmy Winkfield arrived in Paris in 1920, he was continuing his path of grandiose achievements, but he would now be in a city where people of his culture and his race had flourished and would continue to flourish beyond their wildest dreams.  He met and married a fellow exile, the daughter of an exiled aristocrat from Russia.  They had a son Robert and a daughter Lillian. 

Wink was soon back on a horse in France, and soon winning races as well.  He won the ‘Prix Eugène Adam,’ and when he came up against fellow American great, white jockey Lucien Lyne, whom he had known from their Kentucky riding days, Jimmy rode his horse ‘Badahur’ to beat Lyne, riding the favorite ‘Ruban,’ in the race for the celebrated ‘Prix du Président de la République.‘  Lyne was riding for King Alfonso of Spain but that did not faze Winkfield.  As Edward Hotaling puts it, Winkfield rode “through the glitter of the Roaring Twenties in Paris.” 

There can be little doubt that during that time, another famous American in Paris, in between his visits to see ‘the Roman Emperor,’ in between his visits to borrow books from Sylvia Beach at her Shakespeare and Company, in between his encounters with ‘Ford Madox Ford,’ in the streets of Paris, in between his tête-à-têtes with Pascin, with his friends Ezra Pound and Ernest Walsh and their ‘rescue’ of T. S. Elliot from his ‘dreaded’ bank job in London, Ernest Hemingway would have seen Jimmy Winkfield ride throughout the Paris region, or possibly betted on one of Jimmy’s horses, whether at Auteil or at Enghien, or at any of the roughly six racing tracks in the Paris region at that time.

Winkfield retired his saddles at the end of the 1920s.  “I never made anything like the money I made in Russia, but I saved some, and in 1930, when I was 48, I rode my last race.”  By this time, he had stacked up an incredible record of some twenty six hundred wins in America, in Russia, in Austria, in Germany, in Spain, in Italy, and in France.  He then bought a property in Maisons-Lafitte in the northwest suburbs of Paris where he built a stable and developed a training operation.  His home was said to be a glorious space where visiting Americans would drop in and ‘hit him up for food and sometimes money, after loosing at the horseraces.’

Arrival of the Nazis

Wink6Another interruption, much like that of the Bolsheviks on the doorsteps of Odessa in 1919, would force Jimmy Winkfield to abscond yet another time.  It was the onset of World War II and the Nazis had finally reached Paris.  This time, he abandoned his home and stable and moved his family back to America and went to work for stable owner Pete Bostwick in Aiken, South Carolina.  At that time, few in America remembered him or the black jockeys of his and of previous eras.  In 1939, historian Charles Parmer (ex turf official) wrote of the black jockeys, “Today, there may be thirteen of them among 950 licensed jockeys.”  The remaining black riders were mostly in the steeplechase but even there, they had difficulties getting mounts.  One exception was Paul McGinnis who a national steeplechase champion in 1936.

Winkfield worked with Bostwick throughout the war after which he went out on his own and trained and advised varying stable owners.  In Charles Town, West Virginia, Winkfield mentored a young white apprentice jockey, Bill Hartack, who would later go on to tie Eddie Arcaro with a record five Kentucky Derby victories.  At that time, there would have been no black jockeys to mentor.  They were almost non-existent.  According to white jockey Bill Harmatz who mounted the first of his five Derbies in 1955, “When I was riding, there were a couple of black riders who tried to make it, and hell, they never got to first base.  No one would even give ‘em a shot.”

Winkfield left the US for France in 1953 to reclaim and resolve his property in Maisons-Lafitte.   His wife and friends in France convinced him to stay.  In France, he re-saddled his horse ‘Francillion,’ who won the ‘Prix de L’Elevage’ twice.  In 1960, he was back in America for an operation.  “I could have had just as good an operation in Paris, but I knew I was going to die and I wanted to die back in Kentucky.”  The imminence of his death, however, was not to be realized, and he instead visited his daughter to recuperate with his grandchildren in Cincinnati Ohio. 

Denied Entry to Louisville’s Brown Hotel

In 1961, Jimmy Winkfield had not seen a Kentucky Derby in over fifty-eight years.  “Winkfield the Great Wink1Jockey” which The Louisville Courier-Journal had once headlined, was no longer even a footnote in horseracing.  But he was not entirely forgotten by everyone.  Sports Illustrated had done a piece on him in the May issue that had alerted the Turf Writers Association of Winkfield’s return to America.  The Turf Writers Association then decided to honor Winkfield with a banquet at Louisville’s Brown Hotel for that year's Derby run.  Jimmy accepted the invitation in his honor and headed to Louisville.  When he showed up at the Brown Hotel for the function being held in his honor, he was denied entry because he was black.  At seventy-nine, the two time Kentucky Derby champion and last African American jockey to win at Louisville, was forced to wait for a long time outside, amidst the fuss and negotiations between his friends, the Turf writers, and the hotel management.  In the end, Wink was finally ushered in through a front door but not before the imposed embarrassment. 

A man who had counted the last czar of Russia as one of his biggest fans, and who had ridden for and spent much time in the company of European nobility, was denied entry to the very function being held in his honor, at racing venue on which he had left his stamp as a two time champion.  In the end, this must have changed his mind about wanting to die in his ‘beloved’ Kentucky.  The American horseracing champion with probably the most illustrious global career in the history of the sport, and who was the last African American jockey to win the Kentucky Derby, would return to France to live out his wonderful remaining years. 

Jimmy "Wink" Winkfield died in France in 1974, at the age of ninety-one.

Next: Conclusion 

For more on the black jockeys and jockey boy paintings for sale, see

Editors Note: In celebration of the history of black jockeys in the Kentucky Derby, we have spent a week chronicling the history of the great black jockeys who pioneered the sport but were then banished from the sport in the early 1900s, and from much of its history. Kentucky Derby Facts: Black jockeys won 8 of the first 16 Derbies and 15 of the first 28. 13 of the 15 jockeys in 1875's inaugural Derby were black, including the winning jockey, Oliver Lewis aboard his horse Aristides. Isaac "Ike" Murphy became the first jockey to capture successive Kentucky Derbies in 1891 and the first to win a total of three, and James “Wink” Winkfield would win successive races in 1901 and again in 1902 on his horse Alan-a-Dale. Other winners included Alonzo "Lonnie" Clayton, Babe Hurd, James "Soup" Perkins, Erskine Henderson, and Willie Simms.

(Sources include Edward Hotaling’s book, The Great Black Jockeys and The Library of Congress.)



Welcome to Ealy Mays Artworks

Celebration of over 150 years of Black Literary and Artistic development in Paris

Here you will find the works of one of the most prolific African American artists. Based in Paris, France, this selection includes current masterpieces as well retrospectives from a body of over 30 years as an ethnic artist painting in the United States, Latin America, the Caribbean, and Europe. Your choice of paintings, prints, posters, postcards, puzzles, memorabilia, T-shirts, collectibles, accessories,and more, is only a click away. Read more

It is the spectator and not life, that really mirrors art”  The Picture of Dorian Gray …Oscar Wilde

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