Winfield "Winnie" O'Connor

Biography

Winfield “Winnie” O’Connor was a runaway boy who learned to ride under the guidance of trainer W. C. “Father Bill” Daly, who also tutored Hall of Fame jockeys James McLaughlin, Danny Maher, and Edward Garrison in the art of race riding.

O’Connor, who rode his first winner in 1896, was a sensation within a few years. He won 117 races in 1900 to rank seventh in North America, and the following year won 253 races to top the standings.

In an era when jockeys would perhaps receive a $50 gratuity for winning an important races, Hall of Fame trainer John E. Madden paid O’Connor $10,000, win or lose, just to ride Yankee in the 1901 Futurity, which he won.

After finishing fifth in the rider standings with 141 wins in 1902, O’Connor signed a lucrative contract to ride in France for Alphonso Rothschild. During the next nine years, he won 340 races on the flat before increasing weight necessitated him transitioning to riding steeplechasers.

O’Connor returned to America in 1924 and spent some time as a trainer.

Achievements

North America's leading rider in wins — 1901

Other Highlights

Won the Autumn Stakes — 1899, 1901
Won the Brooklyn Handicap — 1901, 1902
Won the New Rochelle Handicap — 1901, 1902
Won the Champagne Stakes — 1901
Won the Futurity Stakes — 1901
Won the Prix du Cadran — 1903
Won the Grand Prix Cercle International — 1905
Won the Grand Prix de Deauville — 1911
Won the Prix du Conseil de Municipal — 1911