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
successful.
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
entrance.
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.
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-Michael Consani