The most notable of these was Asteroid, who went on to win all twelve of his career starts including multiple stakes races and was considered one of the best American racehorses of the nineteenth century.

[2] Robert Alexander died in 1867, and two years later Woodburn Stud manager Daniel Swigert left to establish Stockwood Farm.

However, as he developed into a young man his weight gain hampered his ability to successfully compete in flat racing and for a short time he switched to riding steeplechase horses.

Because he lacked the necessary capital to compete with the millionaires who dominated the sport, Brown used his limited funds to buy horses he believed had great potential, then trained and raced them to the point where their success attracted purchase offers from other wealthy owners.

Similarly, Brown purchased Plaudit from breeder Dr. J. D. Neet and trained the colt until reselling him to John E. Madden, who then won the 1898 Kentucky Derby.

Struggling with rheumatism and tuberculosis, Brown was forced to retire in 1903, reportedly one of the wealthiest African Americans in the state of Kentucky.