Chronicles of the Black Jockeys Volume I: When “Monkey Simon" dealt defeat to “Old Hickory”, General Andrew Jackson

Black Jockeys

The irony of the April 28th New York Times profile of jockey Kevin Krigger, “History Aside, Jockey is Just Out to Win,” is that with “history” truly “aside”, there would hardly be as compelling a story as Kevin Krigger’s, on the eve of the Kentucky Derby.  Krigger’s win at the Santa Anita Derby might not be as otherwise newsworthy were Kevin Krigger not African American and the sport not horseracing.  A win is a win, and a win is indicative of superior strategic and tactical execution by jockeys on superior horses.  So Mr. Krigger’s win is no doubt a superb achievement for which we should laud Kevin, as we cheer him on in Saturday’s Kentucky Derby.

To put ‘history aside’ in a story of American horseracing and the African American jockey would amount to a belief that Nero or Claudius acceded to the emperor’s throne without there having been a Tiberius, Augustus, or even the dictator Julius Caesar, to round out the legacies of the Julio-Claudio dynasties.  Putting “history aside” where the subject matter is the black jockey riding in America's biggest race, ignores the legacy of achievements, which existed before the American Revolution, achievements which evolved up to and after the Civil War, and achievements which continued up the point of the banishment of black jockeys at the dawn of the 20th century.

The legend of black jockeys at the Kentucky Derby was correctly pointed out by the Times: (a) Black jockeys won 8 of the first 16 Derbies and 15 of the first 28; (b) 13 of the 15 riders in the first Derby in 1875 were black, including the winning jockey, Oliver Lewis aboard his horse Aristides;  (c) Isaac Murphy became the first jockey to capture successive Kentucky Derbies in 1891 and the first to win a total of three; (d) James “Wink” Winkfield took third place in the 1900 Derby and came back to win the race  in 1901 and in 1902 with the horse Alan-a-Dale. 

So as we watch Kevin Krigger mount for the 139th Derby at Churchill Downs on Saturday, how then can “history” be truly put “aside” in that which historically, is one of the most monumental areas of achievements in the African American experience?  Austin CurtisParadoxically, the emphasis on Krigger’s accomplishment as the first black jockey to win at Santa Anita in its 78-year history then went on to 'bury' the “history aside” idea, since a ‘first’ by any definition generally means ‘history’ in the making.  

His win might seem less or maybe more jaw dropping if the writers had delineated the number of mounts and participation by black jockeys at Santa Anita in the last 78 years.  We know that the black jockeys were driven out of the race because of owners and trainers who approached the game with a racist view at the turn of the century.  Mr. Krigger himself intimated at the difficulties in getting mounts, which contributed to his movements west, and the affirmative irony here is that Santa Anita's 78 year history commenced only two years after the last great jockeys were driven from the sport.  Santa Anita, it seems, remained pure and free of black jockeys since its inception, in spite of roots which are founded in the legacy of Elias "Lucky" Baldwin, a man who made a fortune with early black jockeys such as Isaac Murphy and Tony Hamilton. 

The truth is that with his win at Santa Anita and his participation and potential success in this Saturday’s Derby, Kevin Krigger might just be putting history "in perspective” and not “aside.”

Horseracing in America commenced with black jockeys, evolved with black jockeys, matured with black jockeys, and became the first organized professional sporting event in America, all through the participation of black jockeys, until they were driven out of the for almost 80 years.  Black Jockeys such as Abe Hawkins rode alongside white jockeys such as the legendary Irish Jockey Gilbert Watson Patrick (‘Gilpatrick’) in a sporting tradition that lasted for more than two hundred years.  Not only were the jockeys African Americans, but so were groomsmen and the winning trainers from the mid 1600s.  The 17th and 18th centuries would see names like Simon, Chisholm, Dick, Charles, Monk, Albert, Cato, and Austin as top slave jockeys riding for southern masters.  The 19th century would see black jockeys like Abe Hawkins, Billy Walker, Oliver Lewis, pass the mantle to the great Isaac “Ike Murphy” who arrived with his good looks and talents in the late 1800s to further transform the sport into one of star power and celebrity, and eventual Kentucky Derby history.

The last great black Jockey, James “Wink” Winkfield who, like Isaac Murphy, had won back to back Kentucky Derby, was targeted and attacked in a Chicago race conflict that broke his horse’s ribs.  Author of The Great Black Jockeys, Edward Hotaling stated that Winkfield’s response to this attack was “simply to just to keep riding”.  Wink was then blacklisted by a powerful stable owner and in face of possible exiled from the game, he took his craft to czarist Russia where he became the Russian National Champion and according to Hotaling, lived a life of luxury. having “enjoyed a suite at the National Hotel in Moscow and caviar for breakfast.”

After leaving Russia, "Wink" would ride and train in other parts of Europe and eventually settled in France where he opened a stable, making Wink another of the pioneering African Americans in Paris during the time of Josephine Baker and WWI ace-pilot Eugene Bullard.  Wink's stable thrived until he had to flee the Nazis with the onset of World War II.   The New York Times lightly points out that on his return to the US, Wink was invited to a celebration in Louisville in 1961, as the guest of Sports Illustrated.  On arrival at the Brown Hotel, the pioneering jockey of the Derby and his daughter were denied entry because of the color of their skin.  What the Times did not mention however, that it took several hours of explanations and embarrassing interventions by the Sport Illustrated and Turf Writers staff before Wink and daughter were allowed to enter, to a segregated audience.  Racing by that time had become so white that no deference was to be given, even for the former champion of the sport.  

The Lost Two Centuries

Nearly 80 years after being banished, the fist black jockey, Marlon St. Julien (on the horse Carule), would mount for the 2000 Kentucky Derby.  What was referred to in the New Times’ article as a “Lost Century,” was in fact a “Lost two or maybe even three centuries.  Not only were black jockeys banished from the sport that they pioneered, but they were also largely written out of the history books.  For over two centuries, racing journals and newspapers such as The American Turf Register, The Sporting Times, Goodwin's Official Turf GuideThe New York Times, and numerous others, had carefully documented the sport, inclusive of the achievements of horses, champion jockeys, owners, and trainers (many of whom were African Americans).  Admittedly, in early days, black jockeys were rarely mentioned by names but only as the "boy of" the stable owner along with the name of the winning horse.  First names were written sometime later and then full names of the jockeys started to occur during the 1800s.  In either case, the documentation was there, yet the black jockeys were then written out of the history.

Horseracing in America did not commence with the Kentucky Derby, nor did it commence in the 1920s.  In fact, horseracing's movements westward towards Kentucky and Tennessee, from its origins on the Virginia-North Carolina border, would only start in the 1800s with the exploits of Tennessee's favorite son, the racing-obsessed Andrew Jackson.  Much later, after the civil war decimated many of the southern plantations, bluegrass horseracing then became a full reality.

According to In Edward Hotaling, some “two centuries before Jackie Robinson” integrated baseball, “blacks competed alongside whites in America’s first national pastime."  The sport that was imported from England was perfected in America by men some of whom originated from the Gambia River Valley region in West Africa where horsemen tended large herds of cattle, thereby already having inherent skills in horsemanship.  These jockeys thrilled hundreds of thousands of fans from New York to Pennsylvania, to Louisiana, to South and North Carolina, to Virginia, to Mississippi, to Tennessee, and Kentucky. 

Old Hickory and "Monkey Simon"

andrew jacksonOne snippet from the legacy of the black jockey and their achievements involve the story of the black jockey boy and his horse who became the principal distractions of a general, in the War of 1812, during his merciless expedition against the Creek Indians, and during his successful 'Battle of New Orleans' against the British.  The brilliance of the black jockey would lead to an obsession by Andrew Jackson out of his failure to triumph over "Monkey Simon" and his horse Maria, an obsession which continued to haunt Jackson, even as President of the United States, wherein he ran one of the biggest racing operations out of the White House.

At some point in the 1800s, the Sprit of the Times sporting weekly described jockey boy Simon (known then by the moniker “monkey” - usual moniker for jockeys of all color) as follows:  “He was not only able to hold a steady reign and maintain a graceful easy seat, but no emergency ever came upon him so suddenly, so unexpectedly, as to cause him to lose his presence of mind or disturb his equanimity.  No danger, no peril was too great for his courage to encounter, and he moved with steady nerve in the face of the most appalling and threatening conflicts.  His integrity was as pure as his courage was firm.  To conquer, was the motto emblazoned by nature upon his mind and heart”

Riding Captain Jesse Haynie’s horse Maria, black jockey Simon would deny General Andrew Jackson victory during what turned out to be many years of battle, and the only defeats to be realized by "Old Hickory.”  The years of duel between the African American jockey and the former senator, judge, then present-day general and future President, would be reported on in the American Turf Register, the Spirit of the Times, as well as from Jackson’s friend Balie Peyton and Judge Tomas Barry, a friend Captain Haynie, the owner of Simon’s horse.  According to Hotaling’s “Great Black Jockeys”, the chronology of events were as follows:

General Jackson invested heavily in acquiring horses to beat Simon and Maria.  In the fall of 1811, he put up his horse, Decatur against jockey boy Simon and Maria.  The general issued the following order to the black jockey, “Now Simon, when my horse comes up and is about to pass you, don’t spit your tobacco juice in his eyes and in the eyes of his rider, as you sometimes do.”  Four-feet six inch Simon was known for his wit and sarcasm for which he got a 'pass' because of his celebrated talents as a rider.  He was a celebrity on the circuit.  He replied to the general, “Well Gineral, I’ve rode a good deal against your horses but (swear) none were ever near enough to catch my spit.”

Simon and Maria won by such a length over Decatur that General Jackson’s horse was disqualified.  Jackson’s friend Balie Peyton would write of his friend, “This defeat aroused the ire and combative spirit of Gen. Jackson almost as much as did his defeat by Mr. Adams (John Quincy) for the presidency, and he swore, ‘by the eternal’ he would beat her if a horse could be found in the United States, able to do it.”   

The next year, in 1812, Jackson bought shares in another horse, Dungannon, which was Maria’s Cato and Wagnerprincipal rival.  With six thoroughbreds running two four-mile distances, Simon led Maria to defeat Dungannon by an even bigger margin than the defeat dealt to Decatur.   Again, Jackson’s friend Balie Peyton wrote, “After the second defeat, Gen. Jackson became terribly in earnest, and before he gave up the effort to beat Maria, he ransacked Virginia, South Carolina, Georgia, and Kentucky.  He was almost as clamorous for a horse as was Richard in the battle of Bosworth Field.”

Jackson then bought four-mile champion Pacolet for three thousand dollars and in the fall of 1813 Pacolet met Simon and Maria in a four-mile heat.  Again, Simon and Maria prevailed.  One writer then wrote of Jackson, “At first he became a very madman. He sent forth torrents of threats, bitter oaths, and declared that he would conquer Haynie’s Maria.  He spent his money like water to obtain success, for he had never known defeat and could not brook it.  Some may think this was a small affair.   Not so with General Jackson.  He regarded nothing as a small affair…”

In the meantime, wisecracking Simon stumbled on General Jackson in a crowd and without fear, proceeded to ridicule the general.  Balie Peyton wrote in the aftermath of Pacolet’s defeat that, “When no friend dared to take liberty with him, Simon met Jackson in crowd and said, ‘Gineral, you were always ugly, but now you’re a show.  I could make a fortune by showing you as you now look, if I had you in a cage where you could not hurt the people who came to look at you.”  This was remarkable in that Simon was a slave and slaves were punished and sometimes killed for perceived disrespect.  But this was also, as his friend Balie Peyton pointed out, the feared General Andrew Jackson who had killed (in a duel) the owner of the horse Ploughboy for failing to pay the forfeiture fee after withdrawing from a race against Jackson’s horse Truxton, only a short time before.

When word came from Virginia that there were horses there that could defeat Simon and Maria, Maria’s owner Captain Haynie offered his horse for a four thousand dollar against any potential competitor.  “Make the race $50,000 if she can beat anything in God’s whole creation,” was Andrew Jackson's response to Captain Haynie.  This led the banjo playing sarcastic jockey Simon to improvise songs aimed at ridiculing the war hero and feared man, General Andrew Jackson. 

Around this time, the expedition against the Creek Indians intervened but in the immediate aftermath of suppressing the Creek Indians, General Jackson would write from Mobile Alabama to his racing affairs manager in 1814, requesting that the manager saddle up Pacolet again to defeat black jockey Simon and Maria once and for all.   Jackson's mind was still obsessed with defeating Monkey Simon.  His people circulated the news that in Pacolet’s last meet with Maria, Pacolet was hurt before the finish line, which led to his defeat.  The meet was set but Jackson would later have to withdraw and pay the forfeiture fee, on realizing that Pacolet was in no shape to race.  Balie Peyton stated, “These repeated failures only made the General more inflexible.  He sent to South Carolina and bought Tam O’Shanter.”

grey eagleSimon, riding Maria, would beat Jackson’s Tam O’Shanter in the fall of 1814 for the Nashville Jockey Club purse.  General Jackson then became even more single-mindedly obsessed with defeating Simon and Maria.  He sent to Kentucky for a horse known to be the fastest mile horse in the United States.  Again, for the fifth time, Simon and Maria defeated Jackson’s horse at Clover Bottom.  Yet another war broke out and General Jackson rode to hastened success, this time against the British in the 'Battle of New Orleans.'  He hurried back to Nashville in no time to try to find yet another horse to defeat Simon and Maria.  

In 1815 the war hero Jackson sought and received a re-match with Simon and Maria against the horse from Kentucky, only to see Simon lead Maria all the way.  A week later, the general found another horse, Western Light, and wavered it against Simon and Maria.  Again, the general saw his horse defeated.  Finally, the general, still convinced that his Kentucky horse could defeat Simon and Maria, got the owner to place the horse a third time against Maria, ridden by Monkey Simon.  This would mark the general’s ninth confrontation with the black jockey and his horse.  Simon’s riding to Jackson’s final defeat at McNary’s Bottom near Sulphur Springs, would be described by witnesses many years later, as an event in which they had never seen such a burst of speed at the end by any jockey and horse before nor since then. 

The famed six-feet one inch general and hero of all wars was defeated by a determined and skilled four-feet six inch black jockey, which sent him into a rage in which he sold his entire stable of horses at his Hermitage stall, with the exception of one.  Jackson then quit the sport of racing which he so loved and obsessed.  It would not be until Andrew Jackson had reached the White House as President that he would resume his horseracing passion, running one of the largest horseracing operations out of Pennsylvania Avenue.  One writer then concluded of Jackson, “Upon the turf, he never met a conqueror, except Berry Williams (black trainer), Monkey Simon, and Hanie’s Maria, and it took the combined three to accomplish what so many had fought for.” 

Years later while President Andrew Jackson sat in the White House as a political warrior, the Turf Jockey LouRegister, described then as the 'Bible' of horseracing, would not let him forget his defeats at the hand of Maria, ridden by Monkey Simon.  It wrote, “General Jackson has conquered all his known and his country’s enemies – except Maria.”  His friend Balie Peyton would embellish: “Although Gen. Jackson conquered the Indians, defeated Packenham (at the Battle of New Orleans), beat Adams, and Clay (for the presidency), crushed the monster bank (the Bank of the United States) under the heel of his military boot, he could not beat Maria in the hands of Uncle Berry (black trainer).”  The Spirit of the Times would conclude that, “In a life crowned with the rarest and most brilliant achievements, Jackson had to face the history of his overthrow by Hanie’s Maria, Uncle Berry, and Monkey Simon.” 

Next: Abe Hawkins

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.) 

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