Henry Skillman, military scout, pioneer mail carrier, and stage driver, was born in New Jersey in late 1813 or early 1814, according to the El Paso County census of 1860. He probably grew up in Kentucky and came west in his twenties. He first appears in written accounts as a courier on the old Santa Fe Trail in 1842, and he later drove the Santa Fe-to-Chihuahua route as a trader. When the Mexican War broke out, Skillman served as wagonmaster in the Doniphan expedition into Mexico in 1846–47, and at the battle of Sacramento in 1847 he distinguished himself as captain of Company B, the Traders Battalion. Later that year he was interpreter and guide for American troops in Mexico. Upon Skillman's return to Santa Fe, he was chosen by Col. Sterling Price to command a party of scouts that traveled from El Paso toward Chihuahua ahead of the American forces.
In 1849 and 1850 Skillman was among the first horseback mail carriers between San Antonio and El Paso. In 1851 the United States postmaster general awarded him the first contract for mail delivery between Santa Fe and San Antonio. He ran the route bimonthly until March 1852, when it became a monthly run. That first run was made with six mules and a Concord coach and was accompanied by eighteen well-armed mounted men, but as time went on the route utilized freight wagons, often accompanied by horsemen leading pack mules. Although there was little call for passenger service initially, the postmaster general began to insist that the service be offered on a regular basis. Skillman could not afford to build and provision the stage stations required for such service. Evidence indicates that he tried to maintain his contract under the new orders, for he had an announcement printed (dated December 6, 1851, but not published until September 1852) offering bimonthly passenger service on the Santa Fe-San Antonio route. Passengers could endure a nineteen-day journey in makeshift canvas-topped farm wagons for twenty-five dollars. But improvements were too little and too late, and in 1854 the postmaster general awarded Skillman's contract to David Wasson. Skillman was residing in Concordia at that time and continued to drive the route occasionally for Wasson. His name appears only sporadically in the logs until the late summer of 1857, when he is recorded as the supervisor of the first coach mail delivery route from San Antonio to San Diego, California. Henry Skillman is remembered as the driver of the first west-bound Butterfield Overland Mail stage, which arrived in El Paso on Thursday, September 30, 1858. Skillman took over the reins of the stage at the Horsehead Crossing station on Sunday morning and arrived in El Paso before dawn on Thursday, having spent ninety-six hours at his position, with no rest or relief.
When the Civil War erupted, Skillman ran espionage for the Confederate forces between old El Paso del Norte and San Antonio. After several successful trips he was tracked and killed on April 15, 1864, at Spencer's Ranch, near Presidio, by a detachment from Company A, First California Cavalry, led by Albert H. French.