Skillman came to the Southwest from Kentucky as a young man, though some accounts have him born in New Jersey in 1813. Henry Skillman wasn’t made for New Jersey.
One of our first glimpses of Skillman comes from Waterman L. Ormsby, a reporter for the New York Herald, who rode on the old Butterfield stage route. Ormsby describes Skillman, who was about 45 years old at the time, as “an old frontier man who was the first to run the San Antonio to Santa Fe mail at a time when a fight with Indians was considered in every contract.”
Ormsby compared Skillman’s appearance to portraits of the Wandering Jew, who taunted Jesus on the way to the Crucifixion and was then cursed to walk the earth until the Second Coming, “with the exception that he carries several revolvers and bowie knives, dresses in buckskin, and has a sandy head of hair and a beard. He loves hard work and adventures, and hates ‘Injuns’ and knows the country about here pretty well.”
Skillman’s prior experience included working as a trader in Santa Fe and Chihuahua and serving as a scout in the Mexican War, where he was part of the Doniphan Expedition that captured what is now Juarez on Christmas Day in 1848. That, combined with a reputation as fierce fighter of Apaches in northern Mexico, made Skillman a perfect candidate for the first U.S. contract to carry the mail horseback from San Antonio to Santa Fe by way of El Paso in 1850. One of the other riders was William “Bigfoot” Wallace. They were two of the lucky ones who lived to tell about it.
The government paid Skillman $12,500 for his services, which might have seemed a lot at the time of signing the contract, but the cost of hiring 18 armed men to make sure the mail made it through Apacheria and Comancheria, plus losses from the angry inhabitants of said regions, compelled him to Washington, D.C., where he lobbied the postmaster general for more money.
While he was there, Skillman met a representative of the Sharps Company, famous for its accurate long-range and high-caliber buffalo guns. Skillman bought 10 Sharps 1851 .52 caliber carbines and armed himself, his drivers and guards with them. Back on the job a few months later, Skillman supposedly shot an Apache warrior from either 200 or 300 yards away, depending on who tells the tale. All accounts end with the Apaches departing in hopes of living to fight another day.
Skillman wrote a letter to the Sharps Company praising the effectiveness of the weapon. The company used the unsolicited testimonial in its advertising. Meanwhile, the Apaches kept their distance. And the stage kept rolling.
In 1854, Skillman asked the government for $50,000 to continue the run. The government responded by awarding the contract to low bidder David Wasson for $16,760. Wasson didn’t last long. He sold it to George H. Giddings in 1854. Skillman continued to fill in on the route and may have partnered with Giddings in the 1850s.
Today, historians know Skillman best as the man who drove the first westbound Overland Butterfield Mail stage from Horsehead Crossing on the Pecos River to El Paso in 1858. A.C. Greene described the feat in his book “900 Miles on the Butterfield Trail.”
“He kept the reins on that first westbound stage from Horsehead Crossing all the way to El Paso, four days on the box without a break, behind four wild mules over 306 miles of the most twisted, nearly waterless, rock-strewn passage on the entire Butterfield trails — an almost superhuman feat of stage driving.”
In 1859, Skillman became the overland mail agent at El Paso. Some historians believe Skillman was not in complete sympathy with the Confederate cause, but when the Civil War started he signed on with the rebel army anyway. He hooked up with a Confederate group that had fled the U.S. and formed an émigré colony in Juarez with hopes of taking control of far West Texas from the California Cavalry column that controlled the region. Skillman knew the country as well as anybody — and better than most — and slipped back and forth from Texas to Mexico across the Rio Grande like a windblown shadow.
The U.S. commissioned Cap. Albert French of Company A of the First California Cavalry to capture its former mail carrier alive, but Skillman would have none of that. He fought to his death — killed through treachery, some say — at Spencer Ranch in what is now Presidio County in 1864.