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  • Michael Consani

Consani’s Corner- The Greatest Jockey You've Never Heard Of

Jimmy Winkfield.

That is the answer to the question who is the

most outstanding jockey most people have never heard of.

Most horseplayers have heard of Bill Shoemaker, Pat Day,

Laffit Pincay is regarded as the best jockeys in the history

of horse racing. Today’s generation looks to Mike Smith, Johnny

Velazquez and Joel Rosario have the top pilots going today.

But the name that almost no one mentions is Jimmy Winkfield.

Jimmy Winkfield was born in 1880. He grew up around horses

near Lexington, Kentucky, the youngest of 17 children. He

began riding at the age of 16, probably to get away from all the

work on his family’s farm.

As an African American jockey, he started to earn $8 a month

from the trainers who spotted his talent but did not want to pay

him anything close to his Caucasian brethren who were not as


Winkfield’s first taste of significant success came in 1900 when he

was allowed to ride the horse Thrive in the

Kentucky Derby. The horse finished third, and Winkfield

became a much sought-after jockey who was finally recognized

for his racing abilities. He returned to the Kentucky Derby in 1901, this time winning the race aboard His Eminence and finishing a length and half ahead of the place horse Sannazarro. The Derby win was the

topper for a great year in 1901 as he won 220 races that year.

1902 was an even better year as he successfully defended his

Derby win by also winning the 1902 Kentucky Derby riding

Alan-a-Dale. By finishing first, Winkfield became one of only

four jockeys ever to win the Derby in back-to-back years.

Despite his unparalleled success, he only was awarded a $1000

bonus for the second Derby win, a figure much lower than those

who had won the race previously.

Winkfield returned for what would be his final Derby in 1903

where he finished second riding the great racehorse Early who

finished just ¾ of a length behind Judge Himes.

Winkfield started to feel growing resentment in the jockey

colony amongst his white brethren. During a race at Churchill

Downs, his home track, Winkfield’s horse was crowded against

a fence by white jockeys, and he was injured in another incident.

Winkfield began to believe that the best horses were being

reserved for whites.

Winkfield decided to leave the United States for Europe. He had

several reasons: a dispute with a top American breeder,

frustration over the 1903 loss, and threats from the KKK all

played a role. For a time, Winkfield lived in Poland and trained

horses owned by an American tycoon there.

In 1904, he won significant races in Moscow, St. Petersburg and

Warsaw, Eastern Europe’s version of the Triple Crown. His

success translated to earning $100,000 a year and granted him

celebrity status in Russia. Amongst his success was winning the

Russian Oaks five times, the Russian Derby four times and the

Warsaw Derby twice.

The Russian revolution of 1917 caused Winkfield to flee the country with his family for France, where he was also successful

in winning numerous races, including the Prix du President de la

Republique, one of France’s major races.

Winkfield enjoyed the French countryside and raised his

children until once again having to flee his home. This time

because the Nazis overtook his town as they occupied

France during World War Two. After the war, Winkfield

returned to his horse farm, and after amassing 2500 career

victories, he began his second career of training horses until he died in 1974.

While he found civility once he left America, not much changed

in later years on return visits. When he was invited back by

Sports Illustrated in 1961 for a reception in Kentucky honoring

living Derby winners, Winkfield was not allowed to enter the

hotel with everyone else but had to enter by a backdoor


It wasn’t until 2004 when he was inducted posthumously into

The National Museum of Racing and Hall of Fame.

The Jimmy Winkfield Stakes at Aqueduct racetrack in New

York is run in his honor. To this day, Winkfield remains the last

African American jockey to win the Kentucky Derby.

Please follow me on my Twitter page @WireAtthe

-Michael Consani

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