Historic Town; Winterset Iowa

 

Winterset Iowa: I was on some business in the Winterset Iowa today. So I took the opportunity of grabbing some photos of the outside of the John Wayne Birthplace Museum and the local veteran's monument.

                                       

The John Wayne Birthplace Museum is surrounded by plaques honoring all of John Wayne's Movies.

 All Photos are by the author

Presentation at Boone & Scenic Valley Railroad & Museum

 

PLEASE JOIN ME ON FEBRUARY 14TH, 2026 AT

THE 

James H. Andrew Museum

in

Boone Iowa 

For a presentation on 

The Train Robbery That Shook the Nation!

Boone & Scenic Valley Railroad

Purchase My Book On Amazon 

The Central States Lawman and Outlaws Historic Association

 

SEE YOU ON THE DUSTY TRAIL!

Frontier and Wild West as Seen Through RPPC Post Cards. By G.C. Stevens

 

Over the last few years I have accumulated a huge amount of copies of famous western figures and RPPC Post Cards. The RPPC Post Cards are my favorite because the subject matter ranges from boots on the ground photos to possible unverified photos of western personalities such as Billy The Kid, Jesse James and Doc Holliday.  The above video features just a few cards from my vast collection.

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.

GALLATIN MISSOURI

Has an Amazing History

Frank James was Tried here for the Winston Train

 Robbery but was acquitted

public domain photo

Repro tintypes from the authors collection

Historical Marker Gallatin Mo

Photos by the author (c)