James E. "Sunny Jim" Fitzsimmons

Biography

Born in 1874 in Brooklyn, New York, on land where the Sheepshead Bay track was built, James “Sunny Jim” Fitzsimmons became a jockey at 15. For five years, he rode mostly at bush tracks, then began to combine riding and training when his jockey career failed to take off.

Fitzsimmons saddled his first stakes winner, Bartender, in the early 1890s and also rode the horse to victory in the Brewers’ Handicap at Pimlico. In 1923, Fitzsimmons got the break which launched him to a career with high-class horses, taking over the stable of Hall of Fame member William Woodward, Sr. Later that decade, Fitzsimmons began training for the Phipps family. That association lasted until Fitzsimmons retired in 1963.

For Woodward’s Belair Stud, he trained Hall of Fame members Gallant Fox and his son Omaha, winners of the Triple Crown in 1930 and 1935, respectively; Horses of the Year Granville in 1936 and Nashua in 1955, both Hall of Famers; plus champions Vagrancy, Faireno, and Happy Gal.

For the Wheatley Stable of Gladys Mills Phipps, Fitzsimmons conditioned Hall of Famer and 1957 Horse of the Year Bold Ruler, plus champions High Voltage, Misty Morn, Castle Forbes, Diavolo, and Dice.

Fitzsimmons won the Belmont six times, the Preakness four times, and the Kentucky Derby three times. His 13 victories in the Triple Crown series stood as the record for 56 years until D. Wayne Lukas won his 14^th Triple Crown race in 2013.

Among the verified 2,275 races won by Fitzsimmons-trained horses were records for the most wins in the Saratoga Cup (10), Dwyer Stakes (nine), Alabama Stakes (eight), Lawrence Realization (eight), Wood Memorial (eight), and Jockey Club Gold Cup (seven), among others. He conditioned 149 stakes winners that won a total of 470 stakes, including eight champions, and seven members of the Hall of Fame.

Shortly after his retirement, Fitzsimmons enjoyed Saratoga’s grand centennial celebration in 1963. The Saratoga racing season was always memorable for Fitzsimmons and his family. Fitzsimmons, who had 17 grandchildren, owned property on Lake Desolation north of Saratoga and the family’s gatherings at “Fitzsimmonsville” were an annual rite of summer. 

Fitzsimmons died on March 11, 1966, in Miami, where he spent his winter months, at the age of 91. He was buried at Holy Cross Cemetery in Brooklyn.

Famed sportswriter Red Smith wrote of Fitzsimmons: “Although he knew a great deal about many things, he knew very little about the stature of James E. Fitzsimmons and the deep and abiding affection he inspired in everybody lucky enough to be touched by his sweetness.”

Achievements

North America's leading trainer in earnings — 1930, 1932, 1936, 1939, 1955

Triple Crown Highlights

Won the 1930 Kentucky Derby — Gallant Fox
Won the 1935 Kentucky Derby — Omaha
Won the 1939 Kentucky Derby — Johnstown
Won the 1930 Preakness Stakes — Gallant Fox
Won the 1935 Preakness Stakes — Omaha
Won the 1955 Preakness Stakes — Nashua
Won the 1957 Preakness Stakes — Bold Ruler
Won the 1930 Belmont Stakes — Gallant Fox
Won the 1932 Belmont Stakes — Faireno
Won the 1935 Belmont Stakes — Omaha
Won the 1936 Belmont Stakes — Granville
Won the 1939 Belmont Stakes — Johnstown
Won the 1955 Belmont Stakes — Nashua

Other Highlights

Won the Saratoga Cup — 1914, 1929, 1930, 1934, 1936, 1939, 1940, 1951, 1952, 1954
Won the Dwyer Stakes — 1922, 1930, 1932, 1935, 1939, 1949, 1955, 1957, 1961
Won the Lawrence Realization — 1924, 1925, 1930, 1932, 1934, 1936, 1938, 1940
Won the Alabama Stakes — 1924, 1928, 1942, 1944, 1946, 1950, 1953, 1959
Won the Babylon Handicap — 1922, 1929, 1930, 1931, 1932, 1938, 1940
Won the Jockey Club Gold Cup — 1929, 1930, 1933, 1934, 1944, 1955, 1956
Won the Wood Memorial Stakes — 1928, 1930, 1936, 1937, 1938, 1939, 1955, 1957
Won the Empire City Handicap — 1930, 1932, 1934, 1940, 1942, 1946
Won the Acorn Stakes — 1933, 1934, 1936, 1939, 1955, 1960
Won the Suburban Handicap — 1922, 1938, 1951, 1956, 1958
Won the Gazelle Stakes — 1924, 1927, 1929, 1930, 1942
Won the Flash Stakes — 1927, 1929, 1932, 1934, 1954
Won the Test Stakes — 1928, 1942, 1951, 1956, 1963
Won the Schuylerville Stakes — 1929, 1933, 1949, 1959, 1962
Won the Coaching Club American Oaks — 1933, 1934, 1942, 1946, 1955