Winfield was born in
Chilesburg, Kentucky (now part of
Lexington, Kentucky) and began his career as a jockey in 1898. His first racing start resulted in a four-horse accident right after the start, for which he was given a one-year suspension. He returned in 1900 to ride Thrive in the
Kentucky Derby, finishing third. He rode in the race again in 1901 and 1902, winning on
His Eminence and
Alan-a-Dale respectively. In 1901, he won 160 races. He competed in his final Derby in 1903, finishing second on Early. He won the
Russian Oaks five times, the four times, the Czar's Prize on three occasions, and the
Warsaw Derby twice. The
Russian Revolution caused him to leave the country in 1917, and he led an evacuation of 260 racehorses of the most valuable bloodlines from
Odesa, Ukraine, trekking for three months on horseback to Warsaw, about 1,000 miles. Only 8–10 horses were lost on the journey. Around 1920, he moved to
France where he resumed racing, scoring numerous wins including the 1922
Prix Eugène Adam, the 1922
Grand Prix de Deauville, and the 1923
Prix du Président de la République. Winkfield had successful racing careers in Poland, Russia, Germany, Austria, Hungary, and France. He raced until 1930 when—at the age of fifty and with more than 2,600 wins to his credit—he began a second successful career as a horse trainer in France. Winkfield lived on a farm near the
Maisons-Laffitte Racecourse on the outskirts of Paris. He remained there until 1941 when Nazis took over his horse farm, after which he traveled to Lisbon and then to New York. In 1953, he returned to the farm at Maisons-Laffitte where he lived until his death on March 23, 1974. == Legacy and honors ==