Will Grant, Pony Express History, and the Stories That Shaped the Cowboy Myth
Myth, legend and the real Old West. That as well as a discussion about how adventures, people met along the way, and insatiable curiosity ensure that we live life instead of simply biding time made for a lively episode of Coffee With Jim. Our guest on the March 15, 2026 episode of our weekly podcast was adventurer Will Grant, author of The Last Ride of the Pony Express: My 2,000 Mile Horseback Journey Into The Old West.
As my childhood passion for books by Zane Grey, exploring ghost towns, family trips in the southwest, and stories of colorful characters led to a John Wayne period in my youth that I never outgrew, the time spent with Will went way to fast. It was a wide ranging conversation about Old West myths and reality, Pony Express history, Karl May western novels, dime novels and the Wyatt Earp legend. François Xavier Aubry and the Santa Fe Trail, Jeff Milton and the Fairbank, Arizona train robbery, and some wild Mongolian equestrian events were also a part of our wide ranging conversation.
If you are like me and grew up immersed in the myth and legend of the Old West you will really enjoy our conversation. Pull up a chair. The coffee’s hot and the history is even hotter. Take a listen, pick up a copy of Will’s book, and find inspiration for an adventure filled life.
Riding Into the Past: Will Grant and the Pony Express Legacy
Grant is not the kind of writer content to study the history of the west from the comfort of dusty archives. He is a lifelong horseman who has worked as a cowboy and trainer across Colorado, Wyoming, and Texas. That skill set adds a level of authenticity to his book that tells the story of a quest to understand the Pony Express and the history of the western frontier the old-fashioned way.
He experienced the cold, heat and rain, tasted the dust, and with two trusted horses as companions immersed himself in the vast landscapes. In The Last Ride of the Pony Express, Grant retraced the historic Pony Express route from Missouri to California through some of the most rugged country in North America.
Grant’s journey took far longer, months rather than the ten days of hardy Pony Express riders, but the slower pace allowed him to experience the diverse landscapes, communities, and traditions where the spirit of the western frontier lives on.
His book blends travel writing, deep historic insight and personal reflection. Grant masterfully offers a vivid look at both the historic Pony Express and the modern American West.
Dime Novels, Karl May, and the Birth of the Western Myth
During the conversation, we explored how the image of the Old West most people recognize today was shaped less by history and more by storytelling. We delved deep into the myth, legend and the real Old West.
Beginning in the 1860s, inexpensive dime novels became wildly popular across the United States. These cheap pamphlet-style books told sensational stories, often with a modicum of truth, of heroic lawmen, daring scouts, and ruthless outlaws.
They sold by the millions and introduced many of the archetypes still associated with Westerns today. The stoic heroes, dramatic gunfights, villains in black hats, and justice riding in on horseback. The stories soon crossed the Atlantic.
German novelist Karl May wrote hugely popular Western frontier novels despite never visiting America. His characters Old Shatterhand and Winnetou became legendary throughout Europe and helped cement the romantic image of the frontier for generations of readers. Even Adolf Hitler was a fan.
Those romanticized stories influenced early Western films, pulp magazines, radio shows, and eventually television programs that carried the mythic cowboy around the world.
Wyatt Earp: From Frontier Lawman to Western Legend
Few figures demonstrate the power of myth-making better than Wyatt Earp. His involvement in the famous Gunfight at the O.K. Corral lasted less than a minute, yet it became one of the most famous events in Western lore.
Through dime novels, biographies, and later Hollywood Westerns, Earp was transformed into the archetypal frontier lawman. But the Old West was full of equally remarkable figures whose stories rarely made it into popular mythology. And some of their adventures make even the most dramatic movie scenes seem tame.
François Xavier Aubry: The “Skimmer of the Plains”
One such overlooked figure is François Xavier Aubry, one of the greatest trail riders of the frontier era. Sadly, many horse most likely were lost during his legendary exploits.
Aubry gained fame along the Santa Fe Trail in 1848 when he rode from Santa Fe to Independence, Missouri in just five days and sixteen hours, an astonishing feat that earned him the nickname “Skimmer of the Plains.” Aubry also pioneered a shorter route along the Santa Fe Trail later known as the Aubry Cutoff, reducing travel distance by more than fifty miles and helping traders move goods faster across the plains.
His short life and tragic end reads like a Western adventure novel. But unlike many dime novel, Zane Grey novels, and countless western movie heroes, Aubry was very real.
Jeff Milton: The One-Armed Lawman of the Borderlands
Another extraordinary frontier figure is Jefferson Davis Milton. His career in law enforcement spanned the era of the western frontier and the first years of the 20th century. Incredibly his career continued even after he lost most of the use in one arm after a shootout.
Milton served with the Texas Rangers, worked as a deputy U.S. marshal, served as the El Paso Police Chief, guarded Wells Fargo express shipments, and was a U.S. Immigration Inspector that patrolled the Mexican border.
It was an incident in Fairbank, Arizona near Tombstone in 1900 that transformed him into a legendary figure. Milton was guarding the Wells Fargo express car when bandits attempted to rob the train. During the gunfight a bullet shattered his arm. He would never have full use of that arm again.
Despite the wound, Milton grabbed a shotgun and returned fire. He killed the wanted outlaw “Three-Fingered Jack” Dunlop and woundrd another. He tossed the safe eys into the desert, bolted the express car door shut, hid the safe keys, and tied a tourniquet around his arm. In spite of the injuries Milton worked as a lawman for decades afterward.
In an era already filled with remarkable frontier figures, a one-armed peace officer seems almost unbelievable. Milton’s story would make for quite a movie, even without exaggeration.
When Myth Meets Modern Tourism and the American West
The myth of the cowboy may have begun in dime novels and early movies, but its influence is still alive today. Across the West and Southwest, the imagery of the frontier continues to shape tourism, politics, heritage preservation, and community identity.
Historic towns, Route 66 communities, and museums often embrace the imagery of the Old West. Cowboy hats, dusty trails, rodeos, and legendary gunfighters translate into marketing. A savvy CVB director will build on the myths, share the real stories behind the legends and give their community a unique identity.
The Real West Is Even More Amazing Than the Myth
As the conversation with Will Grant revealed, the American West is more than a setting for movies and novels. It is a living and evolving story.
The myths of dime novels and Hollywood may pique the imagination. But the deeper history—the stories of Pony Express riders, the forgotten lawmen, the traders, scouts, the Indigenous peoples and pioneers—often turn out to be even more remarkable and inspiring.
So pour another cup of coffee and enjoy the ride. Because out here in the West, the story is far from over.
Thank you. Shared adventures are the best adventures.