Central States Lawman and Outlaws Historic Assoc.
In the late 1800s - and early 1900s The River of humanity flowing west, was both wide and deep. Caught in the current of manifest destiny, were settlers, soldiers, business interests, and Outlaws. It was a perfect whirlwind of the Wild west.
G.C. Stevens
Wild West Purveyor's, Historians and Historic Sites
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Saturday, October 25, 2025
Jesse James Road Trip, Winston Train Robbery Site and Gallatin Missouri. By G.C. Stevens
Photo by the author (Jesse James on the inside of the Winston
Jesse James
Road Trip
Video
The train robbery in Winston, Missouri, occurred on July 15, 1881. The crime stands out as one of the most violent and infamous crimes attributed to Jesse and Frank James. It was one of the gang's final robberies before Jesse's assassination less than a year later. The murders committed that day intensified public outrage and law enforcement efforts against the outlaws. This event occurred during a period when the gang, composed of former Confederate guerrillas, was increasingly fractured after the disastrous 1876 Northfield bank robbery that decimated the Younger brothers' involvement.
By 1881, Jesse James (1847–1882) and his older brother Frank (1843–1915) had been operating as outlaws for over a decade, robbing banks, stagecoaches, and trains across the Midwest. The gang at this time included relatives and associates like Wood Hite (Jesse's cousin), Clarence Hite (Wood's brother), and Dick Liddil (a newer recruit). These new recruits in no way had the same experience or loyalty as the youngers had. The Winston robbery targeted the Chicago, Rock Island & Pacific Railroad, a line the gang had hit before with similar consequences, probably a product of disorganization.
A key motive appears to have been personal vengeance. In 1875, Pinkerton National Detective Agency agents raided the James family farm in Clay County, Missouri, using a bomb that killed Jesse's half-brother Archie Samuel (age 8) and severely injured their mother, Zerelda. Jesse mistakenly believed train conductor William Westfall (1843–1881) had been involved in transporting those agents, as Westfall had worked on similar routes. This grudge fueled the brutality of the attack.
The robbery unfolded at the small railroad depot in Winston (then a tiny Daviess County community about 50 miles north of Kansas City) around 7 p.m. As the eastbound passenger train—carrying about 30 passengers, crew, and an express car—pulled out of the station, five masked outlaws (Jesse, Frank, Wood Hite, Clarence Hite, and Dick Liddil) boarded the rear passenger car.
Jesse, being unmasked and bold as ever, immediately shot Westfall in the back without warning as the conductor collected tickets. Westfall, who had his back turned, died almost instantly and fell from the train near a section house just east of the depot. Eyewitness accounts describe Jesse declaring his identity to stunned passengers, heightening the terror.
Escalation and Second Murder: Chaos ensued as the robbers demanded valuables. Frank James shot and killed passenger John McCullough, a 35-year-old farmer from nearby Cobb, who was traveling with his family. McCullough's death was likely accidental or in the crossfire, but the killings turned public opinion against the outlaws.
The outlaws then forced their way into the express car, pistol-whipping messenger J.L. Penn unconscious when he resisted. They cracked the safe but found only about $900 in cash—far less than the $10,000 they expected—along with some gold dust. Frustrated, they rifled through passenger luggage for watches, jewelry, and small sums, netting perhaps another $200 total. Frank ordered the engineer to brake hard. The gang leaped from the slowing train into a nearby wooded area where they had stashed horses, vanishing into the night. They split up and evaded capture, with no immediate arrests. The entire holdup lasted less than 10 minutes, but the murders left a lasting scar on the rural community.
Aftermath and Legacy
Today, the site is a quiet historical landmark. The original Winston depot still stands at the intersection of Route Y and U.S. Highway 69, marked by plaques from the Daviess County Historical Society. A stone culvert a mile east, along the abandoned Rock Island railbed, commemorates the escape route. The event inspired depictions in art, like Thomas Hart Benton's 1936 mural in the Missouri State Capitol, blending myth with history. It's remembered as a grim chapter in the Old West, highlighting the gang's shift from daring exploits to desperate violence.
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