H. S. P. (Stump) Ashby was born to Benjamin F. and Martina Virginia (Walton) Ashby on May 18, 1848, on their farm in Chariton County, Missouri. He served in Gen. Joseph O. Shelby's command in the last part of the Civil War (see SHELBY EXPEDITION), immediately after settling in Texas, where in turn he was an actor, cattle driver, farmer, and schoolteacher. He was converted to Methodism at the age of twenty and, after a theological reading course, was licensed as a preacher in 1872. He spent the next fifteen years in rural Texas pastorates in Belton, Lancaster, Weston, Stephenville, Rice, and finally Grapevine, Tarrant County, where in 1888 he was apparently removed from the itinerant ministry for his political activities, his criticism of the church's failure to support reform, and an alleged fondness for the bottle.
In 1871 Ashby married Sara Sophia Wisdom in Cooke County, Texas. Before she died in 1876 they had four children. On January 12, 1879, he married Amanda Elizabeth Ray (Wray) at Belton, Texas. They had five children, two of whom died in infancy. Ben, one of his children, had by the time of Ashby's death achieved county political office in Oklahoma.
Ashby's interest in politics began through his acquaintance with Judge Thomas L. Nugent, a member of his Stephenville congregation, who twice ran for governor on the Populist ticket. Ashby was one of the first Farmers' Alliance speakers and organizers in Texas. With Evan Jones, James M. Perdue of Mineola, R. M. Humphrey (white founder of the Colored Farmers' Alliance), William R. Lamb, Harry Tracy, and a few others, Ashby led the antimonopoly, Greenback wing of the Texas Farmers' Alliance. As an early supporter within the alliance of independent political action, he helped lead an independent political movement in Fort Worth that succeeded, in the midst of the Great Southwest Strike of 1886, in electing the mayor of the city. In Waco in May 1888 he helped organize a convention of farmers, laborers, and stockraisers, which led directly to a state Union Labor party convention in July, the first statewide independent political effort in which large numbers of Farmers' Alliance men were involved. As one of the Texas alliance's first district lecturers, Ashby helped pioneer the radicals' tactics of using Democratic hostility to the Sub-Treasury plan of 1889 to split the Farmers' Alliance membership from their traditional Democratic loyalty.
Ashby's Populist career began officially when, with Thomas Gaines of Comanche County and William R. Lamb, he organized the founding state People's party convention, held August 17, 1891, in Dallas; this convention was coordinated with the state Farmers' Alliance meeting in the same city. As state party chairman in 1892 and 1894, Ashby organized the increasingly successful Populist state campaigns. Here his organizational skills and his ability to work with and for his black colleagues counted as much as his effective speaking ability, for which he gained his nickname, "Stump." Ashby was a delegate to the organizing convention of the national Populist party in St. Louis in 1892. During his Populist career he remained active in the Texas Farmers' Alliance; he was state lecturer from 1892 to 1894. In 1896 he ran unsuccessfully for lieutenant governor on the Populist ticket.
That year ended Ashby's public prominence for a while, but he had returned to public activity as a Populist by 1900, when he campaigned in North Carolina for Marion Butler in the latter's efforts to retain his United States Senate seat. In 1902 Ashby attended the Texas state Populist convention as a delegate from Smithfield for the purpose of blocking a prohibition plank in the party's platform.
Soon after this he moved to Mannsville, Indian Territory, where he farmed quite successfully and eventually became president of his local farmers' union. He also returned to politics, this time as a supporter of Democrats William H. (Alfalfa Bill) Murray and Charles N. Haskell. Ashby served in the Oklahoma House of Representatives as a representative of Marshall County to the First Legislature in 1907 and to the Third and Fourth legislatures from Pushmataha County. He died in Octavia, Oklahoma, in May 1923, as well known in Oklahoma as he had been in Texas for his politics and speaking ability.