Boston (1833–1850), a chestnut with a white nose (and often called "Damn his eyes" because no one could beat him), was born in Richmond, Virginia. Boston was the sire of a horse that would become America's leading stud for many years, the brilliant Lexington, but before that day Boston himself was a great—if tempestuous— race horse.
Either cut or shot
As a two-year-old, Boston was won in a card game. Lost by his breeder, the Virginia attorney John Wickham (who had been Aaron Burr's counsel in his trial for treason), he was won by Wickham's friend Nathaniel Rives. Named for the card game and the son of the very good Timoleon (by the great Sir Archy) out of Sister of Tuckahoe (going back on both sides to Diomed and Eclipse as well as, as named, sister to the great Tuckahoe), Boston was willful, and untrainable. Sent to the stable of John Belcher, and then to the trainer L. White, and then back to Belcher, White said, "The horse should either be castrated or shot—perferably the latter."
Belcher trained him with a whip. On April 20, 1836, he was entered into a match in Richmond against a colt of White's. Boston ran away with the race, gaining a long lead, only to stop and sulk. In response, Belcher turned him out as a common hack on the streets of Richmond.
Man vs Horse
Back under saddle, Boston won fifteen races in succession. From Georgia to New York, he raced until he was a ten-year-old, winning 40 of his 45 starts. In those days, races weren't stakes, graded or otherwise, and they weren't run on tidy ovals. They were heats across open country and could be four miles long. Thirty of Boston's wins were at that distance. More than once, his then owner (Colonel W.R. Johnson, called the "Napoleon of the Turf") was paid good money not to race, in order to encourage other owners to enter their horses in an event.
The accepted wisdom is that Boston lost on his merit only once. In May 1842, he met the filly Fashion, the daughter of Trustee and Bonnets o' Blue, in a well touted match race at the Union Course on Long Island, New York. 70,000 people witnessed the event. In the first heat, the nine-year-old Boston (carrying 126 pounds) cut open a long jagged gash on his hip against a rail and both he and five-year-old Fashion (carrying 111 pounds) were upset by the crowd often surging onto the track. Boston led for three miles, but in the end Fashion won it by 60 yards setting a new world record of 7:32½ for a four-mile heat.
A sire of sires
The white nosed "Damn his eyes" went blind as he grew older. Even so, he was leading sire in 1841, 1842 and 1843, beginning his stud career even before he raced against Fashion. (He'd covered 42 mares before the match at $100 each.) He stood, at first, in Hanover County, Virginia, then in Washington, D. C., and was then led over the mountains to Kentucky where he spent his last seasons in Woodford County, Kentucky. It was in Kentucky that he was finally bred with mares of good quality which enabled him to become a leading sire. He was also a noted sire of trotters.
By 1849, Boston was in such poor health he could stand only with the aid of a harness. He was found dead in his stall on January 31, 1850, blind and emaciated from illness. His two best sons, Lexington and Lecomte were born in the Spring after his death.
Boston was one of the first handful of horses inducted into the National Museum of Racing and Hall of Fame in 1955.