The histories of Canada and the United States are so deeply connected that many Americans—about 30%—view Canada as the 51st state. The two nations share the longest international border, measuring 8,892 kilometres, with open air corridors and no restrictions on migration or free trade between them. This partnership could be referred to as the North American Commonwealth, a transnational entity shaped by the Free Trade Act of 1854, which established that commercial benefits and mutual interests serve as powerful unifying forces.
Both countries have significant similarities in their pasts, including similarities in population demographics, economies, cultures, sports, and, regrettably, experiences of racial segregation. The oppression faced by the Black population was rooted in the "Separate but equal" doctrine, which claimed to guarantee equal rights and opportunities for all North Americans, while in reality, racial divisions persisted in everyday life.
In actuality, this doctrine was misleading; Black individuals did not enjoy the same rights as their white counterparts. Applications for universities and higher learning were often denied based on race, and in all aspects of life—including employment, land ownership, military service, culture, and sports—Black citizens were treated as second-class citizens and had limited opportunities.
The realm of horse racing was no exception. By the early 20th century, African-American jockeys found it increasingly difficult to secure employment. This situation is effectively illustrated in the Canadian television series "The Murdoch Inquiry."
(Season 17, Episode 7) The prototype of the black hero in the film was Jimmy Winkfield, a legendary black jockey, the last of the black guys to win the Kentucky Derby twice in a row in 1901 and 1902. He later moved to Europe, where he continued his career as a jockey, and very successfully, and after its completion he became a trainer.
African American dominance on North American tracks in the 19th century
In antebellum colonial America, particularly in the southern states, the occupation of a jockey was viewed as lowly and associated with menial labour, primarily assigned to black individuals. Wealthy plantation owners frequently organised races on their estates, often employing black teenage slaves to ride the horses. It was believed that these young riders had an innate connection with the animals, allowing them to intuitively understand and control them. One notable jockey from the South was a slave named Simon, who was given the nickname "Monkey."
Following the Civil War, the majority of jockeys across the country were black, many of whom were former slaves. They gained a reputation for their integrity and honesty, qualities that became their enduring legacy and a form of capital that could not be taken from them. Abe Hawkins, a former slave, competed at Saratoga Race Course between 1864 and 1867, achieving 25 victories. He, alongside the white jockey Gilpatric, was regarded as one of the top riders in the nation during that period.
Edward Dudley Brown became the first black jockey to win the Belmont Stakes in 1870. Afterward, he transitioned to a trainer role for three decades, during which time his horses claimed victory at the Kentucky Derby. He was later honoured with induction into the American Racing Hall of Fame.
The inaugural Kentucky Derby took place in 1875, with 14 out of the 15 participating jockeys being African American. Black jockey Oliver Lewis rode Aristide to become the first winner of this prestigious event. In 1889, a remarkable occurrence in Brooklyn saw black jockeys triumph in all six races. Three particularly celebrated figures from that era included Isaac Burns Murphy, Willie Simms, and Jimmy Winkfield.
Isaac Murphy
The great American jockey Isaac Murphy, whose name is included in the American Racing Hall of Fame, began racing at the age of 12. Behind his back, he was called "Colored Archer", in honour of the British jockey Fred Archer. He is known for his running style, called the "grand finish", when he made a dash at the finish line, urging the horse not with a whip, but with words and spurs.
He participated in the Kentucky Derby 11 times and was the first to win this race three times in 1884, 1890 and 1891.
By 1882, he was earning $ 20,000 a year. From 1884 onwards, he won the American Derby in Chicago four times within a few years. Murphy himself claimed to have won 44% of his races (628 wins out of 1,412 races). Later calculations showed a different figure - 34% (530 wins out of 1,538 races). But even this understated figure remains unsurpassed by any jockey. His fame and authority were such that if he was replaced by another jockey, the betting odds dropped. In 1986, Isaac Murphy died of heart failure. His remains are buried at the entrance to the Kentucky Horse Park next to the remains of Man o' War.
Willie Simms
Willie Simms, regarded as the top jockey of the 1890s, stands out as the only African American rider to claim the Triple Crown in American horse racing. His accomplishments include victories in the Kentucky Derby in 1896 and 1898, the Belmont Stakes in 1893 and 1894, and the Preakness Stakes in 1898. In 1895, he earned $10,500 and made a notable trip to England, where he became the first African American jockey to secure a win in British racing.
Simms was known for his distinct riding style, characterised by short stirrups and a high seat, with a firm grip on his horse's head. This "crouched" position, which he learned from his mentor, antebellum slave and jockey Abe Hawkins, is now widely recognized as the most effective jockey posture for maintaining balance with the horse. Over his career, Simms achieved a remarkable victory rate of 25%, totalling 1,125 wins. He was honoured with induction into the American Racing Hall of Fame in 1977.
Jimmy Winkfield
The life of Jimmy Winkfield reads like an adventurous film or a fairy tale with no clear ending. Born in 1882 as the 17th child in a former slave family, he began his journey as a jockey in 1894. By 1900, he secured third place at the Kentucky Derby, and in 1901 and 1902, he claimed victory twice, becoming the last black man in history to win this prestigious race. That same year, Winkfield achieved an impressive 220 wins in American races.
However, during this time, black jockeys faced increasing discrimination, leading to fewer racing opportunities for Winkfield and a decline in his career. A fortunate turn came when Mikhail Lazarev, a prominent Russian thoroughbred owner visiting the U.S., discovered Winkfield and invited him to Russia, offering a lucrative contract. Without much hesitation, Winkfield accepted and relocated to Warsaw, then part of the Russian Empire. In Warsaw, he won the Warsaw Derby and earned the title "Black Maestro," amassing 67 victories in just one year.
Later, he moved to Moscow, where he was supported by oil tycoon Leon Mantashev. Here, Winkfield achieved further success, winning the Russian Oaks and Russian Derby four times each, along with the Tsar’s Prize three times and the Warsaw Derby twice. During this period, he married the stunning Alexandra Yalovitsyna.
In 1917, Winkfield left Russia for France, where he tragically lost track of his first wife. He then married Baroness Lydia de Minkwitz, and together they had two children. Unfortunately, Alexandra reappeared in 1926 with deteriorating mental health, ending her days in a costly clinic in the mountains. Their son George, aspiring to become a jockey, fell into gambling addiction and was found dead. These heartbreaking events deeply affected Winkfield, who found solace in his passion for racing.
By the time he turned 50, having won over 2,600 races, Winkfield transitioned from jockeying to training horses at his farm near Paris. In 1941, amidst the German occupation, he lost his farm to the Wehrmacht and faced challenges moving to the United States. Once there, finding work as an elderly black man proved difficult. After the war, the Winkfields returned to their estate in France, where Jimmy Winkfield passed away in 1974.
While Winkfield was celebrated as the Black Maestro in Europe, he remained largely unrecognised in America, where racial prejudice was deeply entrenched. In 1961, despite being invited to celebrations by Sports Illustrated at the Brown Hotel in Louisville, Kentucky, he was denied entry through the front door and directed to the back, an incident that attracted media attention and scandal. In 2004, Winkfield was finally honoured with a place in the National Museum of Racing and the American Racing Hall of Fame, acknowledging his remarkable legacy.
The exclusion of black jockeys from the sport
At the turn of the century, the number of black jockeys in North America began to decrease. The last known black jockey was Jimmy Lee, or “The Black Demon.” In 1907, he won four of the six races on the race card. And in 1908, he outdid himself and won all six races of the day.
The last black jockey to participate in the Kentucky Derby was Jess Conley. In 1911, he was third at Churchill Downs.
It was believed that the reason black jockeys were being replaced by whites was that whites no longer had prejudices against working as jockeys, and so they began to push coloured people off the tracks. In reality, of course, the reason is as old as the world, it was money. It turned out that “Negro work” was decently paid, a good jockey could earn up to $10,000, a lot of money at that time.
Discrimination in racing began, white jockeys created “anti-color unions”. Intoxicated by other people’s successes and money, whites harassed people of colour, deliberately organised intrigue during the race, knocking a black rider out of the saddle, surrounding his horse and not allowing him to break ahead, etc., all dirty tricks were used to ensure that the white man would be the first to finish. Seeing this, horse owners gradually stopped hiring coloured jockeys for their horses, since in this case their success was highly questionable. Racism in its purest form.
This is how the era of black jockey dominance on the North American tracks ended ugly. In recent years, history has slowly turned in the opposite direction.
Once expelled from the Churchill Downs racetrack, black jockeys are returning to the Kentucky Derby. The first to return in 2000 was Marlon St. Julien, who came in seventh. In 2013, Kevin Crigger was a Derby participant, and in 2021, Kendrick Carmouche.
In Canada, the situation is more favourable. The country welcomes migration, so the ethnic composition of the population is quite diverse. Black jockeys are not uncommon at the tracks. And since 2016, it has become widely known about a black woman - jockey Teneka Wolfe-Bell, who won a race at Woodbine Racetrack.