[11] He was then soon sold to Samuel S. Brown, a Pittsburgh, Pennsylvania coal mining magnate and the prominent owner/breeder of Senorita Stud Farm near Lexington, Kentucky.
Under his new owner, Troubadour's race conditioning was taken over by future Hall of Fame trainer, John W. Rogers.
[12] On June 29, in a special mile and a quarter race at Sheepshead Bay, he beat the great Miss Woodford by half a length.
In spite of his limited number of races, his dominating performances led to Troubadour being retrospectively rated American Champion Older Male Horse honors for 1886.
[17] In the Freehold Stakes on August 4, Troubadour suffered a career-ending injury while finishing third to The Bard and runner-up, Barnum.
In addition, in 1890 he sired a homebred for Samuel Brown named Daily America who won the 1893 Lawrence Realization Stakes.