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Wink: The Incredible Life and Epic Journey of Jimmy Winkfield

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Long before Jackie Robinson broke the race barrier and integrated major league baseball, black jockeys had raced side-by-side with whites for nearly two hundred years. Around the turn of the twentieth century, black jockeys were among the best in the horse racing business. Indeed, they became such a threat to their white counterparts that they were banned from racing and their accomplishments, names, and stories have been lost to history. One might ask: who is the latest of the great black jockeys to ride in and win one of our nation's premiere races? What black jockey last won one of America's famous Triple Crown events? Sadly, the answer to both questions is the same: Jimmy Winkfield, in 1902. For the record, he won the Kentucky Derby in 1901 and 1902 - one of only a handful of jockeys to ever win the coveted race in consecutive years. But Jimmy Winkfield's story didn't end in 1902. A jockey without a home, Wink claimed most of the major purses in continental Europe. The All-Russian Derby boasted a purse three times that of the Kentucky Derby, and Wink won it three times in a row.; He was internationally famous and a fabulously wealthy member of the Russian aristocracy when the Bolsheviks overthrew the czar in 1917. Leaving Moscow for Odessa with his Russain wife, Winkfield and others continued to race, then, with the Bolsheviks advancing, marched 200 thoroughbreds a thousand miles to Poland, surviving on horseflesh. By the late 1930s he was training horses on the expansive grounds of his villa outside Paris when German troops occupied his house and stables. After challenging a horse-beating Nazi with a pitchfork, he was forced to flee again. After the war, Jimmy returned to the US only once, in 1961. Invited to the Kentucky Derby banquet at the legendary Brown Hotel, he arrived with his daughter, but because they were black, they were told they couldn't use the front door. Once inside, they were ignored. Wink died in Paris in 1974, still homesick at 94 for the Kentucky bluegrass of his boyhood.

336 pages, ebook

First published October 1, 2004

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Displaying 1 - 12 of 12 reviews
Profile Image for Rena Sherwood.
Author 2 books51 followers
July 24, 2024
I read Hotaling's history of black jockies in America about nine years ago and wavered about reading another by him. So many times, I have been let down by an author's other books.

However, this was not the case. This was an absolute pleasure of a read. It's not only the biography of an unsung American sporting legend, but a good look at world history in the 20th century. Yes, a lot of this book is about horse racing and the people connected to it. But if you are looking for a book just about racing, this isn't it. World events like the Russian Revolution and two World Wars greatly impacted Wink's life, so had to be explained here.

This book was a massive undertaking, considering that not only was Wink dead, but that a lot of his records, such as his birth certificate, have not survived. News articles about Wink during his life were notoriously inaccurrate, including articles published in Sports Illustrated (a publication I personally despise, but that's another story.) The author was clear about what he could and couldn't find out for sure. Be sure to check out the Notes section for clarification, further sources, and some funny stories.

The Acknowledgements at the book's end was four pages long, including thanking the usual suspects like family and co-workers, but also nationally known television news reporters like Dan Rather, and the author of Seabiscuit. There is also an extensive index.

The thing that was most amazing about Wink to me was that, despite being treated like trash in America, he never renounced his American citizenship. The first time someone points a gun at me and says, "Renounce," I'm renouncing.

The second most amazing thing is that Wink rode Man o' War ... but not that Man o' War.

He also helped save over 200 Thoroughbreds from the soviets.

He's not portrayed as a saint or even as a good father, but just those three qualities make his story a riveting one. It's currently up on The Open Library.
Profile Image for Chris.
514 reviews55 followers
June 12, 2018
"Wink" is the bittersweet true story of African-American jockey Jimmy Winkfield who, if he had been born white would be considered one of the greatest jockeys ever along with the lines of Bill Shoemaker, Eddie Arcaro, Bill Hartack, and Johnny Longden. In the early 1900s he became the first jockey to win consecutive Kentucky Derbys. Riding the circuit from New York to New Orleans he won many other big races and prize money for race horse owners. His successes, however, brought envy from white jockeys and, because of his skin color, hatred from racists in America. Since jobs were drying up and gambling was also coming into disrepute in the country, Wink found it necessary to move overseas to race in Russia and Poland. There, because of his ability, he became an instant success winning accolades and prize money for wealthy owners. And amazingly he found respect in colorblind Europe and even rubbed elbows with elite society. As his fortunes grew the countries he rode in became more unstable and when the Czar of Russia was ousted and executed, Wink was lucky to escape with his family and his life. In the process though, and in certainly the most cinematic highpoint of the book, he was able to save hundreds of horses from certain slaughter, and lead them on a 1,000 mile trek to freedom in western Europe. He settled in France where, once again, he was able to build a solid racing career, enhance his reputation, and build a thriving training business. Only to have his horses and property seized when the Germans occupied France in the second world war. Wink's entire career was an epic of successes and confiscations but he was able to cobble together a brilliant racing career in several foreign countries. Which is the point of the book. What a disgrace to our country that so gifted a performer as Jimmy Winkfield was unable to race in his country of birth. "Wink" is a terrific read and a shining example of the heights the human spirit can reach under extremely adverse conditions.
Profile Image for Gabriel.
85 reviews2 followers
September 13, 2025
Incredible story of someone often overlooked in American history. If you loves horses this author goes heavy into detail on which race horses Jimmy Winkfield was accompanying. If you're not as big of a fan of those details then you can maybe skip this one. The protagonist's life story is WILD! He deserves a movie to chronicle all the things he lived through, but as far as the actual writing went I got bored at times with the heavy details related strictly to horse racing. That being said, still worth a read. :)

Profile Image for Constance.
264 reviews
October 25, 2025
I'm a horse racing fan and love bios as well as history so natch this was a very interesting read for myself.
An incredible, courageous life and spectacular career as a jockey and trainer,
this book was extensively researched by the author. Just a bit repetitive in the last chapters.
Lesson: said of someone else but certainly was true of Wink also:
"gifted with a serenity which enabled him to meet good and bad fortune with equal composure,
he rode past whatever challenges life threw at him.
Profile Image for Gary Lewis.
31 reviews1 follower
August 17, 2020
Books reminds us of the greatness and success of African American jockeys in the late 19th century.
The book goes into great detail on Winkfield riding exploits in the US, Western Europe and Eastern Europe.

Highly recommended as too many have tried to ignore the fact that black jockeys were top of the class back then.
4 reviews1 follower
May 14, 2009
I didn't know that African-Americans were prominent as owners, trainers, and jockeys in thoroughbred racing into the early 20th century. For example, in the first Kentucky Derby in 1875, all but one jockey was black. When Jim Crow laws forced them out of American racing some traveled overseas to ride. Jimmy, the star of this book, rides for European royalty and is involved in an incredible horse rescue during World War I. The tone of this book is lively and includes many colorful details. Big on horses, African Americans and history.
9 reviews
August 9, 2008
An unexpected surprise- even if you're not a fan of horses, the adventure of this man is amazing that he compacted all of his adventures into one lifetime... Also a refreshing honest account of how society "rewarded" their best athletes by discarding them due to racial conflict...
Profile Image for Jane.
87 reviews1 follower
February 21, 2013
An interesting story of forgotten and neglected history.
1 review
June 12, 2017
An international star with a heartstoppingly exciting Odyssian life. This story gives you skin chills. Wink only looked forward and up, he let nothing define him but his passions and excellence. Poignantly and grandly told, appropriately presenting a man who should be recognized as Americana royalty.
Displaying 1 - 12 of 12 reviews

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