Jockey Willie Simms, having won the Kentucky Derby twice and the Belmont Stakes twice in the 1890s, capped off his Hall of Fame career by winning the Preakness aboard Sly Fox in 1898. He remains the only Black jockey over his career to have won all three races that make up what for decades has been recognized as the Triple Crown of U.S. horse racing.

Simms’ career spanned an era when Black jockeys dominated horse racing and were among the country’s highest-paid athletes. In 15 of the first 28 installments of the Kentucky Derby, the most prestigious American horse race, a Black jockey rode to victory.

“Although millions of Americans know nothing about it, African Americans were our first professional athletes,” author and journalist Edward Hotaling said in a 1999 interview with The Village Voice. Hotaling wrote “The Great Black Jockeys: The Lives and Times of the Men Who Dominated America’s First National Sport.”

Willie Simms and Lamplighter, circa 1893. (Keeneland Library Hemment Collection)

While working on an earlier book, “They’re Off! Horse Racing at Saratoga,” Hotaling uncovered history that corrected the long-held belief that Simms was the only Black jockey to ever win the Preakness.

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At the 1889 Preakness, George “Spider” Anderson, a Black jockey, arrived at the track with his mount, Buddhist, as the only entrant in the race. Anderson, who was born in Baltimore, had been a jockey since age 12, when, weighing 80 pounds, he rode in the 1883 spring meet in Baltimore, according to the Chronicle of African Americans in the Horse Industry. Within three years, T. B. Davis and Frank Hall hired Anderson to ride horses they owned. They stabled in Maryland at the Ivy City Colony, just outside Washington.

On that Preakness day, Maryland Gov. Owen Bowie, who had led in establishing the Preakness in 1873, learned that Anderson was about to win the race with Buddhist in a walkover. So, he sent his colt, Japhet, as competition.

Willie Simms, circa 1897. (Keeneland Library Hemment Collection)

The day’s events took a violent turn when Anderson went to Bowie’s stables and got into a fight with James Cook, a coachman. According to accounts, both men struck each other with their whips, and Cook suffered a deep cut to his head from Anderson’s lead-loaded whip handle. Anderson was facing prosecution at a court that was set up at the track during that time.

He was allowed to race, however, and Buddhist won in a romp against the overmatched Japhet. No record exists of Cook pressing charges against Anderson.

When Simms became the second Black jockey to win the Preakness, 125 years ago, he was adding to a long list of career triumphs while riding in the most prominent races.

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“Simms won many of the most prestigious races of his era, including the Suburban Handicap, Champagne Stakes, and Jerome Handicap. He won the Second Special four times; the Tidal Stakes and First Special three times each; and the Withers Stakes, Lawrence Realization, Brooklyn Derby, Spinaway Stakes, and Brighton Handicap twice each,” according to the National Museum of Racing and Hall of Fame.

He was among the Black jockeys who led all riders in victories during various years at the end of the 19th century.

“For the first 11 years of the publication of Goodwin’s annual turf guide, the leading rider spot was [held by] a Black jockey five times, with Simms picking up the title in 1893 and 1894,” Natalie Voss wrote in an October 2020 article in the Paulick Report, a publication that covers the horse racing industry.

Simms, born near Augusta, Georgia, in 1870, began racing at Northern racetracks in 1887. He adopted what would become the modern riding position, in which a jockey uses short stirrups and crouches low over the horse’s withers (the ridge between the horse’s shoulder bones).

Willie Simms, aboard Clifford, was in third place early in this race, but he would ride to victory. (Keeneland Library Hemment Collection)

He became a consistent winner using that riding position, as had Abe Hawkins, who had ridden while enslaved. After the Civil War, as horse racing grew in popularity nationally, many horse owners employed their former enslaved people as jockeys.

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Throughout the 18th and 19th centuries, enslaved men, the formerly enslaved and descendants of slaves were the leading jockeys and trainers in American horse racing. In the first Kentucky Derby, in 1875, 13 of the 15 jockeys were Black men, most of whom had been enslaved at birth.

“Willie Simms was part of the second wave of Black horsemen after the end of slavery,” Voss wrote.

The short-stirrup riding position and technique Simms used came more into favor after the white American jockey Tod Sloan used it successfully in England in 1897. It would become known as the “American seat” or the “monkey crouch.”

Simms was the first American jockey to win in England, in 1895. After a short stint there, he returned to the U.S., where he continued to ride for many of the most prominent owners. Those included Hall of Fame members August Belmont I and James R. Keene, as well as Mike and Phil Dwyer, Richard Coker and Pierre Lorillard, according to Simms’ biographical information at the Hall of Fame.

Simms won 182 races in 1893 and 228 from 688 mounts (33.1 percent) in 1894. He won consecutive editions of the Belmont in those years with Comanche and Hall of Fame member Henry of Navarre, respectively. He won the Derby in 1896 aboard Hall of Famer Ben Brush and in 1898 with Plaudit. Overall, based on available records, Simms won 1,173 races from 4,701 mounts (24.9 percent), according to the Hall of Fame.

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“Simms’s victories on the track paid him well — by one estimate, he’s thought to have raked in $20,000 a year at the height of his career (over $600,000 in today’s money),” Voss wrote.

His success, and that of other Black jockeys drew resentment from white riders, fans and writers covering the sport. Sports were in no way immune to the attitudes that led to the rise of Jim Crow laws and policies throughout the country. As Black jockeys solidified their dominance of American horse racing through the late 1800s, they found themselves subjected to more frequent racist behavior by their white competitors, others associated with the sport and fans. White sportswriters were among those who aired their racist sentiments.

From left, jockeys Sam Doggett, Willie Simms and Fred Taral. (Keeneland Library Hemment Collection)

“Turfwriter Hugh Keough was open about his hostility and discomfort with the rise of Black jockeys in the sport,” Voss wrote. She included an example in her Paulick Report article:

“`The praise that was bestowed upon the colored jockeys for their skill was accepted as a compliment to the entire race, and the porter that made up your berth took his share of it and assumed a perkiness that got on your nerves,’ [Keough] wrote.”

Black jockeys and their mounts were put at risk by the racist acts of some white jockeys.

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“White riders began targeting Black jockeys in races with dangerous crowding, boxing in, and other tactics they hoped would make their rivals give up, pull up or be injured or killed,” Voss wrote. “They began warning owners not to hire Black riders – a combination, perhaps, of racism and a desire to eliminate fearsome competitors.”

These incidents began to influence licensing decisions, and gradually, commissions stopped granting licenses to Black jockeys, thereby eliminating them from competition.

Racism and discrimination targeting Black Americans intensified in the 1890s and into the start of the 20th century, stemming from cultural, political and economic forces. The rise of Jim Crow was reflected in the expulsion of African American jockeys, as it was reflected in the expulsion of Black players from Major League Baseball about a decade earlier.

The history of hostility toward Black jockeys that resulted in their expulsion had a permanent impact. For more than a century, Black jockeys have remained largely non-existent in major stakes races in this country. Black men have always had a presence in the racing industry working as grooms and in other roles. But the roles African Americans played as leading jockeys and trainers ended following the era when men like Willie Simms rose to the top of the sport. Since the 1910s, aspiring Black jockeys haven’t been seen at the places that train and produce jockeys for U.S. race tracks.

A painting of Willie Simms can be found at the Pimlico Hall of Fame. Hall of Fame remembrances, old photographs and entries in record books are what’s left as reminders of when Black jockeys, barely one generation after slavery, reigned over America’s biggest sport.

Mark Williams is The Baltimore Banner’s opinion editor.

Mark Williams is Opinion Editor at the Baltimore Banner. He is responsible for selecting and editing opinion articles, essays, and letters to the editor. He also contributes essays that explore the culture and history of the Baltimore region and the people who live here.

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