When the James Gang Ruled the Rails

 | Wild West  | one comment  |  Print This Post  |  Email This Post

At 8 p.m., Jesse and company halted the eastbound train and fired enough shots to keep the passengers inside. The express messenger, William Grimes, filled a satchel with money from the U.S. Express Company’s safe and tried to escape out the back of the express car. Anticipating this move, a gang member intercepted Grimes and struck him on the back of the head with the butt of a revolver, knocking him unconscious. Some 30 minutes later, the outlaws rode off uttering wild whoops of exultation, according to one account. Estimates of the take ranged from $6,000 to as much as $50,000.

Jesse James returned to Nashville after the Glendale robbery, but he was heard from twice in September 1880 in Kentucky–holding up a Mammoth Cave tourist stage and then a Dovey Cove Mine payroll in Mercer. Jesse had a nice haul at Muscle Shoals, Ala., on March 11, 1881, when he robbed paymaster Alex Smith of $5,000. But things took a downturn two weeks later when one of his gang members, Bill Ryan, was arrested in Tennessee. Ryan was eventually convicted for his role in the Glendale train robbery after another of Jesse’s recruits, Tucker Basham, testified against Ryan in Missouri. Basham also mentioned Jesse James as an accomplice, which caused James confederates to burn Basham’s Jackson County home. Basham fled the area.

The James Gang wasn’t through with trains yet. In fact, Frank James returned to contribute his expertise. On the evening of July 15, 1881, a Chicago, Rock Island & Pacific train stopped at Cameron, Mo., and was boarded by two gang members wearing dark suits of clothes [and] high caps, according to the Kansas City Evening Star. A few miles to the northeast, at Winston, Jesse and Frank James and their cousin Wood Hite boarded the train and put on masks. As the train proceeded, William Westfall, the same conductor who had brought the Pinkertons to the Samuels’ farm back in January 1875, collected fares in the smoking car. Suddenly, a tall man with black whiskers and wearing a linen duster (probably Jesse James) yelled, Stop! and ordered the conductor to raise his hands. Instead, Westfall crouched and raced for the back of the car. One of the bandits then shot him in the back. Westfall reeled onto the back platform and tumbled dead off the moving train. The bandits then cut the bell rope, signaling the engineer to stop the train.

Meanwhile, gang members Dick Liddil and Clarence Hite, another James cousin, fired into the locomotive, shattering its windows and ensuring that the engineer pulled onto a siding at Little Dog Creek Bridge. As the outlaws robbed the express car, a curious passenger, Frank McMillan, gaped at them from the platform. A bandit shot him in the head, and McMillan rolled from the train. In the express car, bandits had pistol-whipped the two messengers and robbed the express safe. Exactly how much money was taken is uncertain. The Kansas City Evening Star on July 16 called the crime the most daring, reckless, and cold-blooded murder and robbery ever enacted in the country. Liddil later confessed to participating in the Winston train robbery and said that Jesse shot Westfall and Frank shot McMillan.

Missouri Governor Thomas Crittenden was determined to stop the James Gang once and for all. The governor was under considerable pressure, since Missouri was trying to cast off its reputation as the Robber State. With the aid of Colonel Wells H. Blodgett, attorney for the Wabash Railroad, he called a meeting of railroad and express company executives in St. Louis on July 26, 1881. The officials promised to pay $5,000 each for the delivery of Frank and Jesse James. Another $5,000 each would be offered for their convictions.

The James Gang was not quite done. On September 7, 1881, exactly five years after the failed bank robbery in Northfield, the outlaws stopped a Chicago & Alton train where the tracks ran through Blue Cut, some two miles west of Glendale. Along with Jesse and Frank, participants likely included Clarence Hite, Dick Liddil and a new recruit, Charlie Ford. They used a red lantern to get the train to stop, broke open the express car and struck messenger H.A. Fox with a pistol butt. The gang leader not only didn’t wear a mask but also announced that he was Jesse James. Engineer Choppey Foote later said that the bandits took all the money they could but that the leader gave him $2 to use to drink the health of Jesse James tomorrow morning. The outlaws collected $1,000 at most, as well as jewelry. They made a clean getaway, but there would be no more robberies for the James Gang.

In February 1882, Clarence Hite was arrested in Kentucky and extradited to Missouri, where he pleaded guilty to involvement in the Winston robbery and was sentenced to 25 years in prison. Another cousin of the Jameses, Wood Hite, died early that same year at the hands of Dick Liddil and Bob Ford, Charlie Ford’s younger brother. Apparently, both Liddil and Wood Hite had been vying for the attentions of the attractive widow Martha Bolton, the sister of the Ford brothers. Liddil turned himself in and told all he knew about the James Gang’s robberies.

On Monday, April 3, 1882, Bob and Charles Ford were visiting with Jesse James in his St. Joseph, Mo., home when Bob shot the famous outlaw in the back of the head. Two weeks later, the Fords were indicted on murder charges, found guilty and sentenced to hang. Governor Crittenden granted them full pardons that very afternoon. Many people assumed there had been a conspiracy involving the governor to eliminate Jesse James. In a letter to the Missouri Republican that he supposedly wrote in February 1884, Bob Ford said that he had not been hired by Crittenden or anyone else.

On October 5, 1882, Frank James, with no desire to return to outlawry and fearing the same treatment as Jesse, personally surrendered to Crittenden in Jefferson City. Frank’s wife later said that her husband could not even cut a stick of wood without looking around to see if someone was slipping up behind him to kill him.

In August 1883, Frank James stood trial for the murder of train passenger Frank McMillan during the 1881 Winston robbery. Frank’s star-studded troop of lawyers got him off, overcoming the testimony of a gang member turned informer, Dick Liddil. They got a boost from the governor himself, who testified that Liddil initially told him that Jesse James was the one who had shot McMillan. Furthermore, in February 1884, Crittenden dismissed all other charges against Frank James in Missouri.

That April, Frank did have to stand trial in Alabama for the 1881 Muscle Shoals robbery, but he was found not guilty. By the middle of 1884, 41-year-old Frank James could begin to pursue honest work under his real name. The first bank robbery at Liberty in 1866 and that first train robbery at Adair in 1873 no doubt were impossible to forget, but at least they could now be dusty, distant memories for Jesse’s big brother.

This article was written by Donald L. Gilmore and originally appeared in the August 2000 issue of Wild West magazine. For more great articles be sure to subscribe to Wild West magazine today!

Help HistoryNet by bookmarking to

Tags: Historical Figures, The Wild West, Wild West

You can follow any responses to this entry through the RSS 2.0 feed. You can leave a comment, or trackback from your own site.