Story Time: Jimmy Winkfield, the Craziest Life You Don’t Know About

The name might be familiar, James “Jimmy” Winkfield is a dual-Kentucky Derby winner after all. In fact, he is the last African-American jockey to win the race! He rode His Eminence, and Alan-a-Dale to victory in 1901 and 1902. So he was a jockey more than 100 years ago, and died when he was 93 in 1974. Okay, so what makes this jockey’s story cool enough to talk about 113 years after his last Kentucky Derby win? Buckle your seatbelt because this is going to get intense real quick.

James Winkfield aboard the 1902 Kentucky Derby winner, Alan-a-Dale
James Winkfield aboard the 1902 Kentucky Derby winner, Alan-a-Dale

The year is 1901 and Jimmy Winkfield, a native of Kentucky, had won more than 160 races including the Kentucky Derby on His Eminence. This is post-Civil War America where racism was still a big part of the fiber of much of the country, with the Courier Journal referring to Winkfield as “a little chocolate colored negro.” With all the racing success that year, the Annual Official Guide to the Turf  from that did not include him, due to his skin color. In those days, most of the top jockeys were African American so it was a huge omission. In 1902 on Alan-a-Dale, he became the second jockey to win back-to-back runnings of the Derby after Isaac Murphy. This time, the Courier Journal called him as “black as an ace of spades.” Something interesting with Alan-a-Dale is that the horse was trained by a grandson of statesman Henry Clay, and Winkfield’s mother Victoria was a slave owned by Henry Clay.

The recession of that time really took its toll on racing, as attendance fell and racetracks folded, many white jockeys began replacing black jockeys on the horses, sometimes by force if necessary, and if a white jockey hurt a black one no one cared too much in those days, as was the case with any other white on black crime. There were even riots at racetracks near Chicago over black jockeys getting the mount over white jockeys. With Jim Crowe laws in full effect, and while receiving death threats from the Ku Klux Klan, Winkfield had enough and in 1904 decided to leave his home country for somewhere completely different… Russia.

Winkfield had finally reached the fame he had always dreamed of in Russia. The story goes that he was the personal jockey for Czar Nicholas, but in the Baltimore Afro-American from April 22, 1952 Winkfield says, “they say I rode for the Czar, but I never did. The Czar had a few little horses but I rode and trained for Montichev.” Regardless of the owners he rode for, his skin color had no impact on him getting mounts or the respect and admiration from horsemen and fans. During his time in Russia Winkfield won Russian Champion Jockey three times, the Russian Oaks five times, the Russian Derby four times, the Czar’s Purse three times, and the Warsaw Derby twice. He even won “Czarist Triple Crown”—the Moscow Derby, St. Petersburg Derby, and Warsaw Derby. All over Europe he was a first-call rider for such noble people as a German Baron and a Polish Prince. Not only did he earn 10% of all purses he won, but he was receiving 25,000 rubles a year. At one point was earning 100,000 rubles a year.

James Winkfield with his son George whose mother, Alexandra, was a Russian baroness.
James Winkfield with his son George whose mother, Alexandra, was a Russian baroness.

Finally, he was getting the recognition he deserved–not just as a top African-American jockey, but as an internationally renowned jockey of any color. Unfortunately for Winkfield, all good things must come to an end and so did his success in Russia with a resounding halt. In 1917 the Russian Revolution began and once again, he had to move yet again to a new country. But the trip was not an easy one, him and a few other trainers and owners took 260 horses to Poland. The journey was so treacherous and long–over one thousand miles over the Transylvanian Alps–that at points the group was so low on food that they had to resort to eating their own horses. All humans, and most horses, arrived safely but Winkfield did not end his journey in Poland, he continued on until he reached France.

In France he saw similar success as he did in Russia. He won such races as the now-Grand Prix de Saint-Cloud, the Grand Prix de Deauville, and the Prix Eugène Adam and was a celebrity among the French racing community. The Afro-American newspaper from July 13, 1923 commented, “whenever [Winkfield] showed himself on the thorofares, jubilant natives insisted on saluting him and drinking to his health.” Needless to say, his treatment here was very different than what he was getting back home. After about a decade in France he had 2,600  total wins in his career, and in 1930 retired from riding at the age of 48. Free from racism, he stayed in France on a farm near the Hippodrome de Maisons-Laffitte where he bred and trained racehorses. Unfortunately for Winkfield, he still could not catch a break when in 1940 the Nazi’s had seizes his farm and he had no choice but to move back to the United States where little had changed for him.

In Paris, Winkfield was a celebrity as he is seen here rubbing elbows with Bing Crosby
In Paris, Winkfield was a celebrity as he is seen here rubbing elbows with Bing Crosby

He spent his days in the USA at Aiken training center in South Carolina as well as at Bowie Racetrack in Maryland until 1953 when he returned back to Maisons-Laffitte. In 1961 he was invited to come back to Louisville, KY for a dinner at the Brown Hotel for the National Turf Writers convention. Unfortunately, he still found respect hard to come by in the USA as the hotel staff refused him entry until writers from Sports Illustrated confirmed that he was a guest.

He never came to the USA again, and passed away in France at the age of 93, a celebrity in Europe but almost forgotten in the United States.

In 2004, 30 years after his death he was elected to the National Museum of Racing and Hall of Fame in Saratoga Springs, NY.


The Kentucky Derby: How the Run for the Roses became America’s Premier Sporting Event by James C. Nicholson

2012 Kentucky Derby Media Guide


Dubai World Cup: Is it worth it for Americans?

It’s that time of year! The $10,000,000 Dubai World Cup is right around the corner. With so much money on the line it is no wonder why California Chrome and a few others are going to make the journey. Many people say the trip is too much on the horse and they never come back the same. Is there any base in that?

Here are all of the past American-based runners in the DWC, and what they did after the race when they returned to the USA. If the horse retired after the World Cup, or did not return to race in the USA they were taken off, so some obvious horses (such as Animal Kingdom) are not included.


Cigar (1st)

  • With the Dubai World Cup as his 14th win of his 16 race win streak, three months later he won the Massachusetts Handicap and Arlington Citation Challenge. His streak broke in the Pacific Classic, he came back and won the G1 Woodward and finished his career with a second in the Jockey Club Gold Cup and a third in the Classic.
  • Did Dubai impact his racing? Maybe. Being a 6-year-old horse, its hard to say if his decline in performance was due to the trip to Dubai or his age.

L’Carriere (3rd)

  • Didn’t step up to graded stakes until August ’95, he had decent performances at the Grade 1 level both before, and after Dubai. Third in his first race back (Suburban, a G1) after about four months off.
  • Did Dubai impact his racing? Unlikely.


Siphon (2nd)

  • Winner of the Hollywood Gold Cup and Santa Anita Handicap with a few other seconds and thirds in G1 company before shipping over. After coming home he didn’t race until the end of June and had two seconds, the Hollywood Gold Cup and the Pacific Classic (both to the same horse who won by open lengths), and a fourth in the Jockey Club.
  • Did Dubai impact his racing? Maybe, but probably not.

Sandpit (3rd)

  • He was 8 going into the DWC, with many good performances under his belt both in Brazil and the USA. Leading up he seemed to be at the top of his game. After coming home he spent almost two months off and returned on the turf finishing 6th in the G1 Hollywood Turf ‘Cap, third in the Gold Cup, second in the Arlington Million, third in the Oak Tree Turf Championship and finished his career fourth in the Hollywood Turf Cup.
  • Did Dubai impact his racing? Probably, being eight didn’t help either.

Formal Gold (5th)

  • Before Dubai he was inconsistent sometimes winning sometimes losing both G1 and G3 races. After Dubai, he was the same.
  • Did Dubai impact his racing? Unlikely.


Silver Charm (1st)

  • Before Dubai he finished first or second in all 12 of his races. He returned home with a second place finish three months later in the Stephen Foster. Besides the San Diego Handicap, he continued to only finish first and second. He went to Dubai the next year after doing just okay in 1999, finished sixth, returned in the Stephen Foster then was retired.
  • Did either trip to Dubai impact his racing? Unlikely first time, maybe second.

Malek (4th)

  • A very good Chilean runner, he won the Santa Anita Handicap and finished fourth in Dubai. Came back to the USA and after nearly a year off he had two seconds, then went to Dubai again and was second at six years old. This time he returned just okay, winning only an ungraded stakes at Del Mar. He was going to run in a third DWC in 2000 but was injured and retired.
  • Did Dubai impact his racing? Likely, both times.

Behrens (5th)

  • An okay three year old, his performance declined when going up against older horses. After Dubai he had a couple months off and finished 9th int he Brooklyn Handicap. After that he took the rest of the year off and did much better in 1999 and even won a couple grade ones until his performance plateaued towards the end of the year. Ran in the DWC again in 2000, recovered from the race better than in 1998.
  • Did Dubai impact his racing? Definitely the first time, unlikely the second time.


Malek (2nd)

  • See above

Victory Gallop (3rd)

  • A top level three year old, did very well against older horses in one of the best fields ever assembled in the 1998 Classic. After finishing third in Dubai, he was the first horse since Cigar to win his first race back in America in the G2 Stephen Foster, and won again that August in the G1 Whitney.
  • Did Dubai impact his racing? Unlikely.

Silver Charm (6th)

  • See above

Running Stag (7th)

  • Before Dubai, was a decent runner on dirt but nothing amazing. Lost his comeback race about a month later in England, as well as his return to the USA in the Mass Cap (second both times) and continued to be decent with a few wins in there. The next year, he won his comeback race from Dubai winning an allowance at Belmont and then continued to be an okay runner.
  • Did Dubai impact his racing? Unlikely.


Behrens (2nd)

  • See above

Puerto Madero (4th)

  • Originally from Chile, he ran very well in the USA but would throw in a clunker every now and then. After Dubai he ran two more times, in May and October, and finished 7th and 4th.
  • Did Dubai impact his racing? Likely.

Ecton Park (5th)

  • Did okay against the three year olds. Won his first race back from Dubai in an ungraded staks at Pimlico, and continued to be an okay horse.
  • Did Dubai impact his racing? Unlikely.

Running Stag (7th)

  • See above


Captain Steve (1st)

  • Had only a few impressive wins but many solid performances. Came in 2nd in the Foster after returning home, and finished 3rd and 4th in his last three races.
  • Did Dubai impact his racing? Unlikely.

Aptitude (6th)

  • A good runner, but no good wins to his name before Dubai. Came in third in his first race back, then won multiple Grade Ones.
  • Did Dubai impact his racing? Unlikely.


*Street Cry (1st)

  • Kind of was a US horse, kind of wasn’t. He was pretty good in both the USA and UAE. After the World Cup he came back and won the Foster and was second in the Whitney.
  • Did Dubai impact his racing? Unlikely.

Western Pride (9th)

  • No big wow races, but could hold his own. After Dubai, he came in 11th in the Singapore Airlines International Cup. He won his return race to the USA almost a year after Singapore in the San Bernando, but his performance took a bit of a nose dive afterwards.
  • Did Dubai impact his racing? Can’t say, he put on a lot of miles between March 2002 and April 2003.


Harlan’s Holiday (2nd)

  • Good early on at three, he seemed to get a little worse as time went on. After Dubai, his performances seemed to be the same, after finishing 5th in his comeback race.
  • Did Dubai impact his racing? Unlikely.


Pleasantly Perfect (1st)

  • Multiple graded stakes winner going into Dubai, lost his comeback race after five months off, but won another Grade 1.
  • Did Dubai impact his racing? Maybe

Domestic Dispute (6th)

  • Won a few Grade 2s, but threw in a lot of bad races. After Dubai, never won again but still performed well in Grade 2 races.
  • Did Dubai impact his racing? Unlikely.


Choctaw Nation (3rd)

  • Before Dubai he could hold his own at the top level, and could still hold it after his 5th place finish in his return race. Continued to do well in 2005, ran in Dubai again, sold to Saudi Arabia, and only raced once and finished 8th.
  • Did Dubai impact his racing? Unlikely first time, unknown second.

Congrats (5th)

  • A really good runner but couldnt quite get the win when in graded stakes except for once. After Dubai, he had three months off and raced two more times that year finishing second and third. As a six year old the next year he really declined.
  • Did Dubai impact his racing? Unlikely.

*Lundy’s Liability (7th)

  • Kind of an American horse, but mostly not. Ran four times in the USA before Dubai and won two G2s and also had a 5th and 6th place finish. After the World Cup he stayed in Dubai and never won again.
  • Did Dubai impact his racing? Probably

Ruler’s Court (10th)

  • As a horse who only had a single G2 win, the World Cup seemed too much for him anyways. He won his comeback race, though it was an allowance. Raced once more in an optional claimer and was second.
  • Did Dubai impact his racing? Likely, but he was probably pushed too hard by his connections.


Wilko (2nd)

  • Besides his Breeders’ Cup Juvenile win, he was a horse who could hole his own but was never all that great. His performances consistently got worse as he got older, regardless of how trip to Dubai (which was his best performance besides his Breeders’ Cup).
  • Did Dubai impact his racing? Unlikely.

Magna Graduate (3rd)

  • Overall, he was a very good G2 or G3 horse who would sometimes fire at the G1 level. After Dubai he bounced pretty hard in the Ack Ack (after eight months off), but then got back to his usual performances.
  • Did Dubai impact his racing? Unlikely, he just started to get old towards the end of his career.

Super Frolic (8th)

  • Never was good at even the G2 level, let alone G1. Before Dubai, he was alright. After Dubai, it looks like he actually started to do better.
  • Did Dubai impact his racing? Unlikely.

Choctaw Nation (9th)

  • See above

Brass Hat (DQ)

  • Finished second, later disqualified due to a positive drug test. Before Dubai, he was a very good horse. Occasionally he would throw out a random clunker, but could show up when he needed to. After Dubai, he had a lot of time off finishing pretty poorly in his return race three months later. He would race for four years after Dubai!
  • Did Dubai impact his racing? Maybe, definitely impacted his schedule.


Discreet Cat (7th)

  • Going in he was on a 7-race win streak, but only one of which was a G1. After he came back, he had two races and came in third in both. He had run in Dubai in the past, and came back and ran fine
  • Did Dubai impact his racing? Likely


Curlin (1st)

  • Unlike other USA runners, he went to Dubai early and had a prep race at Nad Al Sheba before the World Cup. Before heading out though, he stamped himself as the best horse in the country. Afterwards, he spent 2008 defending that title and only finished of the board in the Classic. He won his return race to the USA in the G1 Stephen Foster.
  • Did Dubai impact his racing? Unlikely.

Well Armed (3rd)

  • Came to the USA late in 2007, ran in a few graded races and did quite well. After Dubai, he came back and won his return race in July in the San Diego Handicap. He continued to have success in graded races in the USA. Returned to Dubai the next year, and dominated. After his second World Cup, he raced one more time and finished 8th.
  • Did Dubai impact his racing? Not the first time, likely the second time.

A P Arrow (4th)

  • In 2007 he spent the year always showing up and doing well, only getting a few wins. After Dubai he only raced at a higher level than he had before, and his performances declined.
  • Did Dubai impact his racing? Unlikely

Great Hunter (5th)

  • A very promising two year old who got worse as time went on. Before and after Dubai is no real difference.
  • Did Dubai impact his racing? Unlikely.


Well Armed (1st)

  • See above

Arson Squad (11th)

  • Would hit often at the G2 level, and did well at G1 but didn’t win. After Dubai, he dropped a bit and would win G3 and not doing much else.
  • Did Dubai impact his racing? Likely.

Anak Nakal (14th)

  • Before Dubai he won a few G2s and did only okay in his other races. After Dubai he had seven months off and only raced twice. After that he rarely ran in stakes races.
  • Did Dubai impact his racing? Likely.

Race moved to Meydan on the Tapeta racing surface.


Gio Ponti (4th)

  • In 2009, he really started to hit his stride at the G1 turf and synthetic level. After Dubai, he continued that success and ran in Dubai a second time. His performances took a bit of a drop after his second trip, but he was also six years old.
  • Did Dubai impact his racing? Unlikely on his first trip, maybe after his second.

Richard’s Kid (7th)

  • After a few years in maidens and allowances, he hit his stride in 2009 doing well at the top level while winning a G1 and a G2. After Dubai, he lost his first two races and then won two G1s in a row. Spent about a year in Dubai doing terribly, and then returned to the USA again winning a few graded stakes but definitely wasn’t the same horse.
  • Did Dubai impact his racing? In regards to the World Cup, unlikely.

Furthest Land (14th)

  • Didn’t really hit his stride until he was four, and was very good on the turf and synthetic winning the Breeders Cup “Dirt” Mile (run on synthetic). After Dubai, he was definitely not he same horse and did not run anywhere near his pre-Dubai ability.
  • Did Dubai impact his racing? Likely.


Gio Ponti (5th)

  • See above


Royal Delta (9th)

  • Before Dubai she ran exclusively against fillies and was one of the top females in the country. After coming back, she continued on and was the top female performer. Went to Dubai a second time, she came back and still won two G1s but wasn’t as dominant.
  • Did Dubai impact his racing? Unlikely the first time, maybe the second time.

Game On Dude (12th)

  • Before Dubai, he was a top level performer especially when it was in California. After Dubai, he was miles away even more dominant.
  • Did Dubai impact his racing? Unlikely.


Royal Delta (10th)

  • See above

Dullahan (11th)

  • With his best races on synthetic, Dubai seemed like a logical move. Like Curlin he went to Dubai early and raced over the track before the World Cup and did not do well in either race. When he returned to the US, he was not quite as good as he had been.
  • Did Dubai impact his racing? Maybe.


No US-based runners competed

A total of 39 individual US-based horses have competed in Dubai, and then come back to the states to resume their racing career with some who made tried the World Cup multiple times. Of those 39 horses, the ones who seemed to be impacted the most from the trip were Sandpit, Malek (both times), Behrens (first time), Puerto Madero, Lundy’s Liability, Discreet Cat, Well Armed (second time), Arson Squad, Anak Nakal, and Furthest Land. One common theme among these horses however is that many seemed to have been in over their heads anyway.

The horses who seemed to have little to no impact on their racing careers were L’Carriere, Formal Gold, Silver Charm (first time), Behrens (second time), Victory Gallop, Running Stag (both times, Ecton Park, Captain Steve, Aptitude, Harlan’s Holiday, Domestic Dispute, Choctaw Nation (first time), Congrats, Wilko, Magna Graduate, Super Frolic, Curlin, Well Armed (first time), AP Arrow, Great Hunter, Gio Ponti, Rickards Kid, Game On Dude, and Royal Delta (first time).

There were some horses who it was hard to tell, whether or not age was a big factor in their decline or if it was from the trip to Dubai, or hey maybe even a combo. These horses were Cigar, Siphon, Silver Charm (second time) Western Price, Pleasantly Perfect, Brass Hat, Gio Ponti (second time), Royal Delta (second time) and Dullahan.

This is obviously an imperfect list, there are many factors that play into a horse’s decline in performance be it age, miles traveled, or something else. But one thing that shocked me is just how many horses were maybe impacted negatively by their trip to Dubai, with 19 horses on either their first or second trip out.

Definitely makes you wonder, if you don’t win the race, with flights, quarantine and interruption of training, is it true? Is the trip as a whole really not worth it? Sure seems like it, for many runners.