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When Andrew Jackson moved into the White House in 1829, he brought with him from Tennessee a string of race horses and jockeys and a reputation as a leading western turfman. The White House stables were hardly adequate for his prize Thoroughbreds, and Jackson spent thousands of dollars rebuilding them.
Horses had been his passion since boyhood, and by the time he was 15 he was considered a shrewd horse trader. Later, as a lawyer in Nashville, tall, white-haired Jackson had operated the western country's foremost racing stable and stud farm at his home, the Hermitage, a baronial mansion and plantation. At one time he had 16 horses in training there and was part owner of Clover Bottom, a race track.
Some of his Thoroughbreds he trained himself, demanding of them the same relentless determination and physical stamina that were his own chief characteristics. "He worked a horse to the limit of endurance," the late Marquis James said in his Pulitzer Prizewinning biography, "but somehow implanted in the animal a will to win, a circumstance which epitomizes the character and elucidates the singular attainments of Andrew Jackson."
Of the horses Jackson trained, his favorite was Truxton, a big Virginia-bred bay stallion, sired by Diomed, the famous English import whose get sired many top American horses ( Lexington was one). The General had bought Truxton for $1,170 shortly after the stallion's defeat in 1805 by Greyhound, an unbeaten gelding. Convinced that he could win a return match, Jackson vigorously threw himself into training Truxton and raising the $5,000 to cover the side bet.
Interest in the race was so high that people were literally betting their shirts. Jackson accepted $1,500 wagers in wearing apparel, and his friend Patton Anderson put up money, his horse and 15 horses belonging to other people. Many of the 15 had ladies' saddles on their backs, and Jackson, making a fine moral distinction, commented: "Now, I would not have done that." But it is likely that the horses of Mrs. Jackson and her niece, Rachel Hays, were there too.
Truxton won many more races wearing Jackson's colors. The greatest was against Ploughboy, owned by Captain Joseph Erwin of Nashville. The contest between these rival stables grew so heated that later a duel was fought to settle the matter.
The horses had been matched once, but Erwin had called off the race and paid the forfeit.
When the race did run, a contemporary account in the Nashville Impartial Review and Cumberland Repository announced it as follows: "On Thursday the 3rd of April next  will be run the greatest and most interesting race ever run in the Western country between Gen. Jackson's horse TRUXTON, 6 years old carrying 124 pounds, and Capt. Joseph Erwin's horse PLOUGHBOY, 8 years old carrying 130 pounds.... For the sum of 3,000 dollars."
The announcement attracted at Clover Bottom "the largest concourse of people I ever saw assembled, unless in the army," said Jackson. As was then the custom, the match was for the best two of three two-mile heats, horse against horse, winner take all.