The World-Traveling Career of Jockey Anthony Hamilton

Jockey Anthony Hamilton, pictured aboard Pickpocket, dominated racing like few other riders.
Jockey Anthony Hamilton, pictured aboard Pickpocket, dominated racing like few other riders. (George D. Widener collection/BloodHorse)

During the late 1800s – before the Kentucky Derby had any special prestige, before the Triple Crown races had any significance, and before the Daily Racing Form had published its first issue – African-American jockey Anthony Hamilton was in the midst of dominating the sport of racing like few riders before or since.

His services were in demand from sportsmen across the nation. The list of his top mounts read like a “who’s who” of the era’s all-time greats. Such were his skills in the saddle that toward the end of his career, he was able to find success halfway across the world in Europe.

Born in 1866, Anthony Hamilton – frequently referred to as Tony Hamilton – hailed from South Carolina, but it was New York where he would achieve his greatest successes in racing. From an early age, he showed talent as both a jockey and an exercise rider, forging his skills at Brighton Beach racetrack in Brooklyn, N.Y. There, he found work with William “Billy” Lakeland, a rider-turned-trainer who would eventually gain renown as the conditioner of Domino and Hamburg.

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The simple things made Hamilton a natural as a jockey. “He had a good knowledge of pace and a capital seat in the saddle,” opined the Jan. 27, 1891 edition of the St. Louis Post-Dispatch, highlighting two traits that are a prerequisite for any top jockey.

In Hamilton, Lakeland recognized a star in the making, and he took an active interest in helping Hamilton rise to the highest heights of the sport. As described in the May 18, 1895 edition of the Louisville Courier-Journal, Lakeland employed Hamilton for two years before concluding that “he could not afford to pay [Hamilton] the salary that he was really worth” and proceeding to secure Hamilton “a contract to ride for [James Ben Ali] Haggin.”

It was then that Hamilton’s career really took off. Starting at a salary of $3,000 per year, Hamilton had an opportunity to ride Haggin’s future Hall of Fame runners Salvator and Firenze, among others, and his skill in the saddle quickly earned him praise. “It is on a horse’s back and in a driving finish that Hamilton shows to advantage,” reported the July 29, 1888 edition of the Buffalo Sunday Morning News, “There … his painstaking and powerful methods of developing every particle of speed are apparent.”

It was during his days riding for Haggin that Hamilton first met his future bride, Anna L. Messley. Their wedding in St. Louis attracted high-profile attention in newspapers of the day, in part because it was such a lavish and impressive affair. The Jan. 12, 1891 edition of the New York Times published a short notice from St. Louis explaining that: “Nearly two hundred invitations have been issued, and many guests from New York and other cities are coming. ... Hamilton is said to be wealthy, and it is known that he has spent $1,000 in one jewelry house here for presents.”

Hamilton and Messley were married on Jan. 22, with the three-time Kentucky Derby-winning rider Isaac Murphy serving as best man. The following day’s Pittsburgh Daily Post detailed the impressive scope of the event: “For the occasion this evening the whole of the upper floor of the building was secured for the wedding. A swell caterer furnished the supper, and a florist had given the grand reception hall the appearance of a tropical flower garden.”

Hamilton’s success aboard Haggin’s best horses soon placed his talents in great demand. By the beginning of 1893, Hamilton had essentially taken a tour of racing’s greatest stables, riding not only for Haggin but also such legendary sportsmen as August Belmont, Mike Dwyer, Foxhall Keene, and Pierre Lorrillard. Securing his first-call services required increasingly greater sums; 1893 saw Hamilton sign to ride for Belmont, and the Feb. 6 edition of the St. Louis Post-Dispatch outlined the details of the contract: Hamilton would “receive $10,000 and the usual $25 for winning and $15 for losing mounts.”

Although Hamilton never won a Triple Crown race – he only rode in the Belmont Stakes, with his best finish a runner-up effort in 1889 – he made his reputation by winning many of the most significant races in New York and New Jersey. At one time or another, Hamilton nabbed victories in all three legs of the old “New York Handicap Triple Crown,” winning the 1896 Metropolitan Handicap aboard Counter Tenor, the 1895 Suburban Handicap aboard Lazzarone, and the 1889 and 1895 Brooklyn Handicaps aboard Exile and Hornpipe, respectively. Kingston, Lamplighter, Potomac, and Tenny were other respected runners that Hamilton guided to victory in major races.

On one occasion, Hamilton was asked to speak about some of the great horses he had ridden, leading the jockey to reflect on the sheer number of them that he’d been involved with. “I have, I guess, had the mount at different periods on [all the greats], that is, of course, those that have become famous since I reached the top of the ladder,” said Hamilton in the Feb. 6, 1893, edition of the St. Louis Post-Dispatch.

Hamilton and Suburban Handicap winner Lazzarone
Hamilton and Suburban Handicap winner Lazzarone (George D. Widener collection/BloodHorse)

One horse Hamilton did single out was Raceland, who played a role in one of Hamilton’s most memorable rides. On that particular occasion, owner Joe Ullman presumably had a large wager on the outcome and offered Hamilton $1,000 – a huge sum for the era – to “win with Raceland and do so [by] as far as you can,” as recalled in the St. Louis Post-Dispatch. Hamilton followed orders and “got off in front with his mount and never let up driving him until the finish has been passed.” Raceland’s margin of victory was estimated at nearly a quarter of a mile.

But as time carried on, Hamilton’s dominance began to wane. Reuniting with Billy Lakeland in the mid-1890s sparked a few more big wins, including his score aboard Hornpipe the Brooklyn Handicap, but the general consensus among journalists of the day was that Hamilton was riding tentatively and no longer taking risks the way other jockeys did.

Then, toward the end of 1895, Hamilton’s wife unexpectedly passed away from tuberculosis, which seemed to further affect Hamilton’s career in the saddle. The following year, his riding suffered to the extent that he was suspended by the Brighton Beach Racing Association due to a series of unsatisfactory rides aboard Hornpipe, and on Jan. 22, 1897, Montana’s Anaconda Standard reported that Hamilton was “very ill with pneumonia.” This onslaught of obstacles seemed to take a toll, and Hamilton found few opportunities to ride during the late 1890s. At the time it seemed probable that his career was winding down.

But then Billy Lakeland gave Hamilton one more chance, and the May 2, 1900 edition of the Buffalo Enquirer praised the result. “It seems if as jockey Anthony Hamilton has been given a new lease of life in the saddle,” the paper explained. “He has displayed recently more energy in the saddle than has been noticed in some time … Just now he lacks confidence … But with time Hamilton will regain a portion, at least, of his old confidence and skill.”

The confidence seem to come after Hamilton made a bold decision in 1901 to pull up stakes and shift his riding tack to Europe, where several other American jockeys were enjoying widespread success. “Hamilton has signed a contract to ride this year for Baron John Harkyani, in Austria,” reported the Feb. 25, 1901 edition of the New York Times. This final stage of Hamilton’s career saw him rise to international prominence with major stakes victories in Austria, Hungary, and Poland; he was successful enough that he signed an $8,000 contract to ride in Russia for the 1902 season.

Sadly, while in Europe, Hamilton became ill with tuberculosis, and after a year-long battle he passed away in France on Feb. 21, 1904. Following his death, Hamilton's body was returned to New York and buried in Brooklyn, not far from Brighton Beach where he first rose to prominence as a jockey.

Hamilton’s career was one of ups and downs, but when he was at his peak, few could challenge his dominance. “He stands right at the top of the list among American jockeys,” wrote the Jan. 22, 1891 edition of the St. Louis Post-Dispatch at a time when many of Hamilton’s most significant victories were still ahead of him.

Maybe it isn’t a stretch to simply say that Anthony Hamilton was the best jockey of his era.

Fun Facts

  • Hamilton also rode the great Henry of Navarre on three occasions. Although he wasn’t in the saddle for any of the colt’s most memorable triumphs, Hamilton did guide Henry of Navarre to second-place finishes in the Sapling Stakes and Select Stakes, plus a win in an allowance race at the original Monmouth Park.
  • In 2012, Hamilton was inducted into the Racing Hall of Fame.
  • According to the National Museum of Racing and Hall of Fame website, Hamilton maintained a phenomenal 32.5% win rate throughout 1890 and 1891, a sustained level of success that is extraordinarily difficult for any jockey to achieve.

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