Jimmy Winkfield: An Amazing Jockey.

Jimmy W on Alan-a-Dale.jpg

I’m in a play called “Jockey Jim” by Larry Muhammad, and I must share Jimmy Winkfield’s extraordinary story with you. He was an extraordinary man, an African American man, born in 1882, in a family of 17 brothers and sisters, in rural Kentucky. He went from earning $8/month to commanding $1000 per race! He  became one of the greatest African American jockeys ever. He started racing in 1898. And won two straight Kentucky Derbies, in 1901 and 1902. And in the next two Derbies, he came second and third!

In the early 1900’s, he was blacklisted because he “changed his mind” about riding a horse. As well, there was intimidation by the Ku Klux Klan, violence by white jockeys, and the involvement of big money, not conditions conducive for African American jockeys to race. So he accepted an invitation to race in Russia for Czar Nicholas II and became a big star in Russia. He regularly rode winners in Russia, Poland, France, Austria, Hungary, England, Spain and Italy! But by 1917, with the Bolshevik revolution and the rise of the Communists, racing in Russia was done. 

He then led 250 top tier thoroughbreds on a 1,100 mile journey from Russia to Warsaw. He resurrected his career in France in 1922. Also marrying a Russian Baroness named Lydia de Minkiwitz. They lived in a farm near Maison Lafitte, 11 miles outside of Paris. They lived like royalty, hobnobbed with the likes of Josephine Baker, Paul Robeson, Bing Crosby, and Ernest Hemingway!

He earned $100,000, which at the time was an enormous amount of money!

After he retired from horse racing at 48 years of age, he became a celebrated horse trainer in France.

As a result of the Nazis coming into power, he and Lyddy moved back to the USA in 1941.

Back to segregation, discrimination, back to a time when blacks were called darkies, and much worse. He had to become a hired hand on a horse ranch and Lyddy had to clean people’s houses. They lived through it.

They moved back to Maison Lafitte in 1953 and they operated one of the most successful racing stables till the 1960’s.

Lyddy died in 1958, and Jimmy in 1974 at age 92.

What a dashing and debonair man, what a gifted horseman! And to what success he and his wife rose and to what depths did they sink in racist America. And then again rose up in Europe!

Jimmy  (and Lyddy) had to be an amazingly strong person to have withstood all that life threw his way and to come out of it victorious and on top. I respect this man so much, and by the end of the play, when Lyddy and Jimmy walk into the Brown Hotel, I am almost crying, even though I am playing Lyddy and am not supposed to cry, but it is such an emotional moment! And Gary Brice who plays Jimmy, plays him to the nines! Perfect in his understated acting and emotions. Understated, something I don’t do so well, garners a lot of pathos. If Jimmy Winkfield were here today, I would certainly tell him how much I admired his strength, his intelligence and his resilience. And that I am so proud to be doing this play about his life!

Jockey Jim review in Arts-Louisville

Me melodramatic?!? Never!!!

 Rediscovering the Past

Gary Brice as JImmy Winkfield and Samina Raza as his wife Lyddy rehearsing play JOCKEY JIM. photo by Bud Dorsey

Gary Brice & Samina Raza in Jockey Jim.
Photo by Bud Dorsey.

Jockey Jim

By Larry Muhammad
Directed by William P. Bradford II

Reviewed by Keith Waits

Entire contents copyright © 2016 by Keith Waits. All rights reserved.

When the Kentucky Derby rolls around, most theatres in the Louisville area close up shop, the assumption being that audiences will be otherwise occupied with Derby Festival events. So Kentucky Black Repertory bucks the odds with a new production of Jockey Jim, a play that ties into the history of “The Greatest Two Minutes in Sports.”

Jimmy Winkfield (1882 – 1974) was one of the great jockeys in thoroughbred racing, winning two consecutive Kentucky Derbies in 1901 and 1902. It is his journey after those victories, however, that is the compelling story of Larry Muhammad’s script: a lucrative career in Russia before and during the Bolshevik Revolution; a rich life in Paris with his wife, Lydie de Minkwitz; and an ignoble return to the United States, confronting Jim Crow segregation.

The structure of the play is roughly chronological, although some nonlinear juxtaposition early on felt confusing and seemed to lack any real purpose. The real draw of Winkfield’s story is that a sharecropper’s son became such a cosmopolitan figure, hobnobbing with celebrities and living on the periphery of pivotal moments in 20th century history. It is especially intriguing that Muhammad shows Winkfield on somewhat agreeable terms with Communists and Nazis without calling into question his loyalty as an American. Much is made of the contrast in attitude toward Negroes in Europe as opposed to America, although the Nazis are openly racist, just highly pragmatic about Winkfield’s usefulness.

The scenes that play best find Winkfield struggling with the latter part of his life in the United States. As the title character, Gary Brice is a young actor playing the aging horse expert with notable grace and care. He sidesteps cliché with wisdom and observation and establishes the character’s dignity with confidence. As Lydie, Samina Raza lends the Russian heiress a melodramatic quality that pushes the envelope a bit, but it is a quality that speaks to the character’s background and how emblematic it is of the peaks in Winkfield’s life in Europe.

Ernie Adams gives Winkfield’s employer, the casually racist Beauchamp, an easy, vile authority that still allows for some small but significant shifts in the audience’s perception of his character. Marcus Orton and Joe Monroe provide scene-stealing comic energy as two of Jimmy’s buddies — ne’er-do-well knuckleheads who do little to develop the plot but inject worthwhile color into the mostly sober-minded material. Francisco Juarez does a fine job as Milo, the Hispanic jockey who rides Winkfield’s horse in the 1950s. In its inclusion and treatment of this character, Muhammad’s text is fully aware of yet another shift in opportunities for minorities in thoroughbred racing.

Winkfield’s European adventures are generally more serious in tone, with a host of supporting characters who are notably less developed. Francis Whitaker and Spencer Korcz are professional as Russian compatriots, two limited roles that never rise above narrative necessity in the text. Better impact comes from a charismatic Sidney Edwards and Tyler Madden as Josephine Baker and Paul Robeson. These characters exist only as brief thumbnails of the iconic figures from Winkfield’s Paris life, but the actors occupy that territory with the presence and glamour befitting the two famed entertainers. In the same mold, Patrick Alred is miscast as an avuncular Bing Crosby, but he does yeoman’s work in this and other small roles. Tom Pettey wisely underplays Von Oppenheim, the German officer who is Winkfield’s contact, proving it is best to not push too hard when wearing a swastika on your arm. Tom Luce, Owen Kane, and Tim Stone fill out the ensemble with skill.

Jimmy Winkfield’s story is certainly worth exploring, and Mr. Muhammad works hard to investigate its social ramifications. Winkfield’s position as a man without a country is effectively mined to investigate the subversion of African-American history in the 20th century. Jockey Jim restores Winkfield to his rightful place in history.

Jockey Jim

April 30, May 1-6, 8:00 pmTickets: $20 cash at the door

Kentucky Black Repertory
at the Henry Clay Theatre
604 South Third Street
Louisville, KY 40203

Jockey Jim Almost in the Home Stretch!

Seems like all I’ve been doing is learning my lines for “Jockey Jim”or going to rehearsal at the Henry Clay. This play is written by my friend and great playwright Larry Muhammad, (  and I have the female lead, Lydia de Minkiwitz, James Winkfield’s wife who was a Russian baroness, so I have my share of lines, and I have learned them, YES! And I’m saying them all with a Russian accent, ha! I have five costume changes, below is a picture of my favorite costume, haha, you guessed it, it’s glam!

(See more about the truly amazing Jimmy Winkfield here:

We’re in tech and dress rehearsal week, which means 5+ hour long rehearsals everyday this week. We open on Saturday. It is amazing to see how far we’ve come, from “No way. This is never going to get done!” to “Hey we’re doing it!” to “No (ok, not many) problem, we’ve got this!” This happens every time a play is put on, every time I’ve been in a play I’ve started with “Are you kidding me?! How many lines do you want me to learn? Yeah right!” and ended with “Wow, I learned ALL the lines!” And all the stage directions, and all the smiles, and hugs, tears, pouts, and champagne toasts (we’re actually doing all that in Jockey Jim.) And so it is with “Jockey Jim.”

Annoying, exhilarating, amazing, heart in your throat process, that finally yields one hell of a performance and one hell of a good play. We’re getting there, it’s all coming together. Today we had our first dress rehearsal, and from now on, they’re all dress rehearsals. Tomorrow, we add makeup and hair too. I have to wear a gray wig for the older scenes, oh well…

My character’s age goes from 30’s – 70’s. Difficult for me to do aged, struggling with that. I keep forgetting I’m supposed to be 65 years old, oops… hope I don’t give the director a conniption…

I hope all my Louisville friends come to see us, it’s going to be one fine play!

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In the dressing room, with my favorite costume, of course! 🙂


Dialogue from my play “Jockey Jim” by Larry Muhammad.

I play Jimmy Winkfield’s wife, Lydia de Minkiwitz, a Russian Baroness! This dialogue is from when we move to the US and are not doing very well. I’m doing my best Russian accent while still trying to be intelligible at the same time hahaha.

James Winkfield was the last of the African American great jockeys, he won the Kentucky Derby in 1901 and 1902! But after his retirement he was largely forgotten. A fascinating story!

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