 Mary moved with her son and new husband Benjamin Wells to Rushville, Missouri around 1857.Fry, who weighed less than 120 pounds, was assigned to the first leg of the westbound route of the Pony Express delivering it from the stables in St. Joseph, Missouri a few blocks to a ferry across the Missouri River before carrying it on to Seneca, Kansas.Ads for the Pony Express said, "Wiry young men, preferably orphans to ride 20 miles..."

While there are no photographs of the start of the Pony Express, the old tin-type of Johnny Fry standing next to Johnson William Richardson in a sailor's hat and jacket, with Charlie Cliff and his brother Gus Cliff pictures the riders hired by Lewis for Russell, Majors, and Waddell.