Sunny Jim: A beloved great of the game

James "Sunny Jim" Fitzsimmons (Maryland Jockey Club)

James “Sunny Jim” Fitzsimmons won 13 Triple Crown races en route to becoming one of the most respected and beloved trainers in American racing history

By Brien Bouyea
Hall of Fame and Communications Director 

It had the audacity to rain throughout the afternoon James “Sunny Jim” Fitzsimmons retired from thoroughbred racing after a 78-year association and love affair with the sport.

The rain, however, mattered little on this day. Nothing was going to dampen the celebration that took place on June 15, 1963, at Aqueduct. A life’s work was complete, an enduring legacy was assured, and it was time to pay homage to one of the most esteemed individuals in the history of American thoroughbred racing. A crowd of 48,160 disregarded the raindrops and gathered at Aqueduct to honor the grand old man of racing, the 88-year-old legend, Mr. Fitz.

When he finally decided it was time to retire, Fitzsimmons had crafted an extraordinary body of work. He won a documented 2,275 races, including 13 Triple Crown events (a record that stood unsurpassed for 56 years until D. Wayne Lukas won his 14th Triple Crown race in 2013). Along with training two Triple Crown winners — Gallant Fox and Omaha — Fitzsimmons set records for the most victories in the Saratoga Cup (10), Dwyer Stakes (9), Wood Memorial (8), Alabama Stakes (8), Lawrence Realization (8), and Jockey Club Gold Cup (7), among others. He conditioned 149 stakes winners, of which eight were recognized as champions. seven of those champions were inducted into the National Museum of Racing’s Hall of Fame.

Success, however, did not come quickly or easily for Fitzsimmons. He was not born into a life of privilege and his association with racing yielded nothing of significant distinction until he was well into his 40s. Sunny Jim mucked stalls in his youth and failed as a jockey long before he ever achieved anything of note in racing. After already having spent decades in the sport, Fitzsimmons seemed an unlikely candidate to emerge as a master conditioner of elite racehorses, but that is precisely what he became.

James Edward Fitzsimmons was born July 23, 1874, in his family’s cottage in Brooklyn. Five years later, the land on which the residence was situated was purchased by Leonard Jerome and his partners and became the home of the Coney Island Jockey Club’s splendid Sheepshead Bay racetrack. Around 1885, Fitzsimmons secured his first job in racing at Sheepshead Bay doing stable and kitchen chores for the Brennan brothers’ stable.

It wasn’t long before Fitzsimmons went to work for prominent owners Mike and Phil Dwyer. At the time, the Dwyers were campaigning some of the greatest horses in the sport, including Hanover and Miss Woodford. Fitzsimmons worked and slept in the stables for the Dwyers and eventually was given an opportunity as a jockey at the age of 15 at New York’s Brighton Beach racetrack on Aug. 7, 1889. He finished fourth with his first mount, a colt named Newburg. It took him more than a year to win his first race.

At 17, Fitzsimmons married Jennie Harvey and together they raised five sons and a daughter. Two of Fitzsimmons’ sons, James and John, eventually because assistant trainers with the stable.

Fitzsimmons was never able to get a leg up on the top Dwyer horses. The stable used the best riders in the sport, including the great Jimmy McLaughlin, one of the top jockeys of his era. Recognizing he would pilot only second-string horses for the Dwyer brothers, Fitzsimmons decided to make a go of it on his own.

Throughout the 1890s, Fitzsimmons was a nomad, competing for meager purses at various “outlaw” tracks such as Gloucester and Guttenberg in New Jersey; Saint Asaph and Alexander Island in Virginia; Elkton, Marcus Hook, and Sunny Side in Maryland; and Maspeth on Long Island. Fitzsimmons was far from the big money and glamour of the sport. As a rider, Sunny Jim was never able to distinguish himself. He described his abilities in the irons as “pretty mediocre.”

“I was riding at Guttenberg when they first held night racing under the lights,” Fitzsimmons recalled in a 1963 interview in The BloodHorse. “I hadn’t had a winner in some time. When I got a chance to win one I was halfway down the stretch when I saw something coming at me and I went to a drive. I needed that winner. When we pulled up I found out we had won by 10 lengths. The other horse was my shadow chasing me. I knew enough to outride my shadow.”

Recognizing he would never be able to adequately support his family as a jockey, Fitzsimmons decided to give up riding and attempt a transition to training racehorses.

“I once walked a horse 15 miles to a racetrack, rode him in two heats and walked him back,” Fitzsimmons said of another experience during his days as a jockey. “The purse was $5 and I earned 25 cents.”

Fitzsimmons began training in the final years of the 19th century. He won his first race as a trainer on Aug. 7, 1900, with Agnes D. at Brighton Beach. Fitzsimmons formerly rode as a jockey. A moderate success early on, Fitzsimmons led the trainer standings at Maryland’s Pimlico Race Course for a meeting in 1904. It was about this time that Fitzsimmons was tagged with the moniker “Sunny Jim” by New York World sports editor George Dailey, who likened Fitzsimmons’ cheery disposition to a popular cartoon character.

The early clients Fitzsimmons trained for were an interesting mix of characters from all walks of life. They included Johnson N. Camden, a senator from Kentucky; Herbert Pratt, president of Standard Oil; Vernon Castle, a famous stage dancer; Richard Croker, a Tammany Hall politician who slipped out of the country when the organization was accused of stealing public funds; and even Frank James, the notorious Civil War guerilla soldier who later made a living robbing banks, stagecoaches, and trains.

Although some of his owners were notable it did not lead to prosperity — or good horses to train — for Fitzsimmons. In 1906, Fitzsimmons established Aqueduct as the base for his public stable, but he continued to bounce around. He went north to Canada and later back to Maryland when New York racing was shut down by anti-gambling legislation in 1911 and 1912. Sunny Jim finally tasted some success on the big stage in 1922 when he won the Suburban Handicap for James F. Johnson’s Quincy Stable with Captain Alcock, who also defeated Kentucky Derby winners Exterminator and Paul Jones that year in the Pimlico Cup.

The following year, William Woodward, Sr. hired Fitzsimmons to train for his emerging Belair Stable. In 1926, Fitzsimmons added another prominent client, Gladys Mills Phipps, who was establishing Wheatley Stable at the time. In 1929, Fitzsimmons conditioned 4-year-old Diavolo to victories in the Jockey Club Gold Cup, Saratoga and Dixie handicaps, and the Saratoga and Pimlico cups for Wheatley, while also beginning his association with a Belair 2-year-old named Gallant Fox, who won the Flash and Junior Champion stakes that year and hinted at greater things to come.

With two rising stables as his main clients, Fitzsimmons was finally playing the game — and winning — at the highest level. In 1930, Fitzsimmons was so enamored with Gallant Fox’s potential that he convinced the distinguished former jockey Earl Sande to come out of retirement and return to the irons aboard the promising Belair colt. After winning the Wood Memorial, Gallant Fox was victorious in the Preakness Stakes, which was run before the Kentucky Derby that year. The “Fox of Belair,” as he became known, then won the Derby by three-quarters of a length before securing a three-length victory in the Belmont, replicating an accomplishment of Sir Barton 11 years before. The achievement was referred to as the “Triple Crown” by Bryan Field in the New York Times the day after the Belmont.

Gallant Fox was famously defeated that summer at Saratoga in the Travers by Jim Dandy, but he added victories in the Dwyer, Arlington Classic, Saratoga Cup, Lawrence Realization, and Jockey Club Gold Cup to his 1930 ledger to finish his 3-year-old campaign 9-1-0 from 10 starts.

In 1934, Fitzsimmons began conditioning a 2-year-old colt from Gallant Fox’s first crop of offspring. Omaha, a Belair homebred, grew to 16.3 hands and weighed 1,300 pounds. He needed time to develop, which was demonstrated by the fact he won only one of nine starts at 2, but, like his sire, Omaha showed flashes of potential brilliance.

That potential turned into production in 1935, as Omaha became the second Belair runner to annex the Triple Crown. He remains the only son of a Triple Crown winner to duplicate the feat. Ben Jones and Bob Baffert are the only trainers since Fitzsimmons to win the Triple Crown twice.

Fitzsimmons continued to thrive throughout the 1930s. He was America’s leading trainer by earnings in 1930, 1932, 1936, and 1939. Fitzsimmons won a third Derby during the decade with Johnstown in 1939, while also adding the Belmont in 1932 (Faireno), 1936 (Granville), and 1939 (Johnstown). All of Sunny Jim’s 10 classic winners during the decade hailed from Belair Stable.

Success in the Triple Crown events eluded Fitzsimmons in the 1940s, but he was still at the top of the game. In 1940, Sunny Jim trained Fenelon to victories in the Travers, Jockey Club Gold Cup, Lawrence Realization, and Empire City Handicap. The following year, Fenelon added the Brooklyn, Manhattan, and Whitney handicaps. In 1942, Fitzsimmons sent out Vagrancy to 11 wins, including the Coaching Club American Oaks, Alabama, Beldame, Test, Delaware Oaks, and Pimlico Oaks. Although the remainder of the decade was not barren for Fitzsimmons, it certainly paled in comparison to his success in the 1930s.

In the late 1940s, Fitzsimmons began training for Mrs. Phipps’ son, Ogden Phipps, who purchased a major portion of the breeding operation of Col. E. R. Bradley. One of the early success stories for Ogden Phipps was the distaffer Busanda, who won the Alabama, Suburban Handicap, Top Flight Handicap, Diana, and two editions of the Saratoga Cup under the care of Fitzsimmons.

William Woodward, Sr. died in 1953, passing his racing stable on to his son, William, Jr. The year before he died, Woodward, Sr. bred the great Nashua. Sunny Jim celebrated his 80th birthday during Nashua’s 2-year-old season in 1954 — and what a year it was! Nashua won the Juvenile, Grand Union Hotel, Hopeful, and Futurity at 2 to cement his status as the best of his crop. In 1955, Nashua set a track record of 1:54⅗ in the Preakness and won the Belmont by nine lengths. He also won the Florida Derby, Wood Memorial, Dwyer, Arlington Classic, Jockey Club Gold Cup, and a $100,000 match race vs. Kentucky Derby winner Swaps.

At the same time he had Nashua on his shedrow, Fitzsimmons also conditioned champion fillies High Voltage and Misty Morn for Wheatley Stable. With Nashua, High Voltage, and Misty Morn leading his barn, Fitzsimmons was the country’s leading trainer by earnings for a fifth and final time in 1955 with purses totaling $1,270,055.

As Nashua went into retirement following his 1956 season, another standout emerged for Fitzsimmons in the form of Wheatley’s Bold Ruler. At 2, Bold Ruler won the Youthful, Juvenile, and Futurity. At 3, he provided Fitzsimmons with his fourth Preakness victory and his 13th and final win in the Triple Crown series.

After being named co-Horse of the Year along with Dedicate in 1957, Bold Ruler returned the following year as a 4-year-old to win the Suburban, Carter, Stymie, and Toboggan handicaps. Fitzsimmons still had some good years as a trainer ahead of him, but the culmination of his superlative career took place in 1958 when he was inducted into the National Museum of Racing’s Hall of Fame. As usual, Sunny Jim remained humble.

“Nobody can make a bad horse good. The main object is to avoid making a good horse bad, and a lot of it is just a matter of luck,” Fitzsimmons said. “I came into this game with nothing to give it. Racing gave me the happiest life you could want. Racing doesn’t owe me a thing, but I owe the game a hell of a lot.”

Fitzsimmons had developed arthritis in his spine, which significantly bent his frame in his later years, but he soldiered on and went about his work with his trademark passion and persistence. In his final few years as a trainer, Fitzsimmons won the Alabama in 1959 with High Bid; the Spinaway, Demoiselle, Fashion, and a division of the Schuylerville with Irish Jay in 1959; and the Mother Goose and Black-Eyed Susan in 1961 with Funloving. On the day he was honored at Aqueduct in 1963, Fitzsimmons won the Miss Woodford at Monmouth Park with the Bold Ruler filly King’s Story.

From 1907 through 1963, Fitzsimmons won 2,275 races. Since there are no accurate records from his days at the outlaw tracks a complete record of Sunny Jim’s training ledger does not exist. However, it has been documented that his 149 stakes-winning horses won a total of 470 stakes.

Ogden Phipps said his family had “such a wonderful association with Mr. Fitz for 38 years. The record speaks for his skill as a trainer, but what has been more important to us has been Mr. Fitz the man, a man of great character whose outlook on life and concern for his fellow man endeared him to all fortunate enough to know him.”

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. Sunny Jim, who had 17 grandchildren, owned property on Lake Desolation in the hills above the Spa and the family’s gatherings at “Fitzsimmonsville” were an annual rite of summer. 

Fitzsimmons died 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.

“Mr. Fitz was associated with the best in racing during his brilliant career,” said James Cox Brady, chairman of the New York Racing Association at the time. “He was a credit to the sport in every sense.”

Famed sportswriter Red Smith wrote of Sunny Jim: “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.”

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