Charles Littlefield

Hall of Fame Inductee, 2000

Legend – Jockey


The first running of the Queen’s Plate in 1860, staged at the Carleton course on a tract of land in the West Toronto Junction, was captured by Don Juan, a 5-year-old bay gelding, and his American-born jockey, Charles Littlefield. He was one of the elite horsemen of the 19th century and would also win the Plate in 1862 on Palermo.

After retiring from the saddle and taking up residence in Paterson, N.J., then a famous rendezvous for turfmen, Littlefield became one of the leading trainers in America. He managed the stables for prominent owners Milton H. Sanford and James Ben Ali Haggin. Among the outstanding horses in his care were Hira, later the dam of Himyar, Preakness, Monarchist and Salina, afterward the dam of Salvator. He won the 2nd running of the Belmont Stakes with General Duke in 1868 and the 1885 Preakness Stakes at Pimlico with Tecumseh.

In the 1850s and ’60s the services of Littlefield were in demand. Wiley and crafty were terms used to describe Littlefield. A Toronto newspaper, The Leader, said “To succeed in getting him to ride a horse is about half the battle won. He is certainly the most finished and masterly rider in Canada.”

In the inaugural Queen’s Plate Littlefield escaped injury when he was thrown off his mount, Paris, just after the start of the first heat. The 27-year-old rider from Rochester, N.Y., then reportedly replaced his brother, Nelson, on Don Juan for the second and third heats and handily won the “50 Guineas” and the Plate for owners James and John White of Milton, Ont. In 1863 it appeared that Charley’s tactics of “accidentally” falling out of the saddle in the first heat and then winning the next two heats on another horse would succeed. But a protest was lodged against his mount, Willie Wonder, who two weeks later was disqualified as it had previously earned public money.

Born in 1833, Littlefield had a seasonal residence in Toronto and later was one of the leading riders in North America. He began his riding career in Toronto as a teenager in the 1850s before accompanying the famed Ten Broeck stable to England in 1857, riding Prior, Prioress, Umpire, Starke and Lecomte for the famed gambler and horse owner. Littlefield rode Kentucky, who captured the Inauguration Stakes at four-mile heats at the opening meeting of Jerome Park, N.Y., in 1866.

Late in the 1880s he formed a partnership (it lasted until 1892) with Charles Boyle of Woodstock, who also would be inducted into Canada’s Horse Racing Hall of Fame. Lady Reel, afterward the dam of U.S. Hall of Fame great Hamburg, was a member of that stable.

In 1912 Littlefield visited Toronto to witness the 53rd running of the King’s Plate. His trip to Toronto enabled him to visit his son, Barry, who was in the midst of a brilliant career with the powerful Joseph E. Seagram Stable. Barry Littlefield trained five Plate winners for Seagram, including Hall of Fame great Inferno. Another of Charles’ sons, Fred Littlefield, won the 1888 Preakness Stakes, riding for his father-in-law, R.W. Walden, a famous trainer who was inducted into the U.S. National Hall of Fame at Saratoga, N.Y.

Littlefield died in July, 1915, in Brooklyn, N.Y., at the home of his son-in-law, Lawton Garside.