James R. Keene: Money King, Racing Tycoon

James R. Keene (middle) with son Foxhall Keene (left) and an unidentified man.
James R. Keene (middle) with son Foxhall Keene (left) and an unidentified man. (Keeneland Library)

An Englishman by birth, James R. Keene was a mercurial figure on Wall Street and a powerhouse owner in the sport of Thoroughbred racing.

Growing up in post-gold rush California, Keene purchased a few mules and entered the hauling trade. His customers included the Bonanza silver mines, where he piled up $6 million through bold and shrewd trading. Eventually, Keene was appointed president of the San Francisco Stock Exchange. In 1876, he traveled in a private Pullman car to the heart of the country's financial center in New York City in search of far greater scores.

James Robert Keene

Born: 1838

Birthplace:  London, England

Residence: Cedarhurst, Long Island

Died: Jan. 3, 1913

Hall of Famers: Bred Hall of Famer
Kingston and owned Domino, as well
as breeding Hall of Fame inductees
Colin, Peter Pan, Commando,
Maskette and Sysonby

Belmont winners: Spendthrift (1879),
Commando (1901), Delhi (1904),
Peter Pan (1907), Colin (1908)
and Sweep (1910)

A slightly built man who dressed in a black Victorian frock coat and derby hat, Keene sported a pointy beard and possessed cold, penetrating grey eyes. He had nerves of steel and an iron will. Chomping down on a dozen unsmoked cigars a day, Keene battled some of “Gilded Age’s” most powerful financiers, Russell Sage, Jay Gould and J.P. Morgan among them. Time and time again, Wall Street never saw Keene coming.

Wrote English turf writer Edward Moorehouse: “Though he repeatedly stood to lose a million pounds in five minutes, he never lost a night’s sleep. He was often defeated, but not for too long … he was probably the greatest stock-exchange strategist that the world has ever seen.

“He was the admired and envied and feared king of Wall Street. With nary a close friend, even his own son Foxhall called him ‘Mr. Keene.’ ”

Keene became a racing man in 1879 and is recognized as the most successful Thoroughbred owner and influential breeder of his era. Spendthrift carried Keene’s white and blue polka-dot colors to victory in the 1879 Belmont Stakes as well as the Jersey Derby, Champion Stakes and the Lorillard Stakes. A top-class stallion, Spendthrift is perhaps best remembered as the great grandsire of Man o’ War.

Spendthrift died at Castleton Stud, which Keene developed into one of the premier powerhouse breeding operations in the history of American horse racing.

From 1893 to 1912, the Thoroughbred nursery bred 113 stakes winners, among them four of the greatest to compete on American racetracks: Colin, Commando, Peter Pan and Sysonby.

More names on Keene’s roster of top-flight runners were Domino, Delhi, Kingston, Sweep, Voter, Cap and Bells, Celt, Ultimus, Ballot, Maskette, Black Toney, Ben Brush (1896 Kentucky Derby winner), and Penchant as well as others foaled on Castleton’s Lexington, Ky. soil.

In 1908, London Sportsman Magazine declared that Keene possessed “the greatest lot of racehorses ever owned by one man.”

Foxhall, named for Keene’s son, became the first American horse to win the Grand Prix de Paris in 1881, then the most influential race in France. The following year Foxhall won England's Ascot Gold Cup, the renowned English race.

The colt’s steely determination on the turf was equally matched on Wall Street by Keene, a master at buying stocks cheaply, then manipulating the share price upward until a crazed public snapped them up.

“Keene did not bet on fluctuations, he made them,” observed turf writer Moorehouse.

Keene twisted the stock market to fit his own purpose. Then in 1884, his gambling luck ran out when he went broke in an attempt to corner the Chicago grain market. Huge losses piled up and cost Keene everything he owned. Undeterred, a few years later he engineered a remarkable comeback after being hired by Wall Street investor William Havemeyer to manage a stock fund. Keene’s overarching skills of market manipulation soon brought J.P. Morgan and William Rockefeller into the fold and once again the “Silver Fox” emerged as a powerful titan in the New York financial community.

James R. Keene
James R. Keene (Keeneland Library)

After recovering from financial ruin in 1891, Keene was spending heavily on horses with a newly made fortune. Purchased for $3,000, Domino would mark Keene’s return to the sport. Known as the "Black Whirlwind,” Domino was a champion and the best sprinter of his time from 1893-1895. His name would become synonymous with speed on the racetrack.

Another top-class runner in the early 1900s was Sysonby. Named for a famous hunting lodge, his groom Ernest Shackleford described Sysonby as “a common, cheap-looking, lop-eared colt.” Standing only 15.1 hands as a 3-year-old, Sysonby won his first start by 10 lengths at Brighton Beach Racetrack in July 1904. He decisively whipped all his rivals in five more races that season.

Sysonby kicked off his 3-year old campaign in a dead heat for first with older horse Race King in the Metropolitan Handicap. It would be the last race where Sysonby was even challenged. He won the Great Republic and then won the Tidal Stakes, Lawrence Realization, Iroquois, Brighton Derby, and Century Stakes. Undefeated in nine races, he triumphed at distances from a mile to 2 1/4 miles. Sysonby was named 1905 Horse of the Year, as well as champion 3-year-old male, and earned $184,438 in his 15-race career.

In June 1906, the horse became the victim of smallpox, or possibly a liver disease, dying in his stall at Sheepshead Bay. More than 4,000 people turned out to attend his burial in front of Keene's stables and to pay tribute to the great horse. Sysonby was later exhumed, and his skeleton has been on display since 1907 at the American Museum of Natural History in New York City.

Another Keene mega-star was Colin, unbeaten during his 15-race career. Colin is revered as one of the greatest horses ever. Foaled in 1905, he was a son of Keene’s stallion Commando out of the mare Pastorella. At two, Colin won the Futurity, Great Trial (carrying 129 pounds), Saratoga Special, and Flatbush. Colin shattered Belmont's five-furlong track record in the winning the National Stallion and established a North American record for seven furlongs when winnning the Champagne. The only tough test he faced at two came in the Eclipse Stakes, which Colin won by a head. At three, Colin raced just three times winning the Withers and the Belmont Stakes. In his final race at three, Colin scored an easy win in the Tidal Stakes, covering the mile and a quarter in a swift 2:04.

Keene (right) with Harry Payne Whitney.
Keene (right) with Harry Payne Whitney. (Keeneland Library)

Afterward, Keene boasted that Colin could fill the grandstand at Sheepshead Bay even without the gambling that had recently been outlawed in New York. Colin was sent to England as a 4-year-old, but pulled up lame in a workout and was retired to stud and later returned home to Castleton Farm.

“At the time of his [retirement], Colin was the greatest racehorse in America,” Keene declared. “He could beat every horse he ever met without extending himself. Most of his races were mere gallops for him.”

As for Keene, he became a founding member of The Jockey Club in 1894 and demanded regulatory action in a sport where crooked jockeys and bookmakers drove race-fixing schemes that were sinking Thoroughbred racing. He invested part of his fortune in the construction of Belmont Park in 1905. His last winner was a colt named Helmet who carried Keene’s famed silks to the winners' circle in Saratoga on August 23, 1910.

At age 72, Keene sold Castleton and sailed to Europe. A stomach ailment brought him home in December of 1912. He died in New York City on Jan. 3, 1913.

On Wall Street. Keene was revered and feared as a spectacular risk-taker who rode the stock market to fame, fortune, and bankruptcy — and worked his magic to come back again. But his influence in U. S. racing and breeding is deemed his greatest accomplishment. In an interview with the New York Herald, Keene put his love for his racehorses this way:

“It is the gratification of possessing something that you know is a little better than that possessed by anybody else. Beyond that, it is a matter of intense personal pride. It is not the sum the horse may earn; it is not the possibility that he may be employed for speculation that makes him desirable, because racing for gaming is not sport.

“It is the fact that he is a wonderful work of nature, a fine, high-spirited, perhaps gentle and intelligent, animal that is a little superior to all others of his time, and whose courage is tested by races he runs and the results that follow.”

Fun Facts

  • His Wall Street bitter rival Jay Gould once quipped, “Keene arrived in New York by private railroad car, and [Gould] would send him home to California in a boxcar.”
  • When railroad strikes threatened the entire U. S. transportation system and the railroad market crashed, Keene bought up all the railroad stock and became known as the man who saved the industry.
  • Many turf writers mentioned Sysonby’s name alongside of Man o’ War as the best in the game during the first two decades of the 20th century.
  • Keene’s colt Foxhall shocked the European racing world when he won the Grand Prix de Paris in 1881.
  • Domino was Keene’s favorite runner. When the brilliant stallion died on July 29, 1897, Keene inscribed these words on his tombstone: “Here lies the fleetest runner the American turf has ever known, and one of the gamest and most generous of horses.”
  • Keene was one of the founding members of The Jockey Club and the Sheepshead Bay race track.

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