RIDGE RUNNER CHRONICLES: Perpetuating the Legend of Jesse James as the Ultimate Outlaw

By Editor | December 4, 2025 |

A friend sent me a story about Jesse James and the 1876 Northfield, Minnesota bank robbery in which several innocent persons were killed during the robbery. That story piqued my interest in Jesse James and the James Gang, who terrorized folks in the Mid-West from 1866 until 1882. Despite the fact that he was linked to numerous brazen robberies and some shooting deaths in connection with those robberies, some people still regard Jesse James in a favorable light as the ultimate outlaw and some even regard him as the “Robin Hood” of the West. Others say he was nothing but a thug.
Jesse James and his brother, Frank, had horrible, violent childhoods on a farm in Missouri preceding the Civil War. As a young man during the Civil War, Jesse joined up with the pro-southern “bushwhackers” known as Quantrill’s Raiders, who were implicated in a number of horrific killings in Missouri and Kansas. After the War was over, Jesse drifted into a life of crime in order to survive and became involved in multiple armed robberies from Alabama to Minnesota.
The robbery that resulted in Jesse ironically being being perceived as the Robin Hood of the West was a train robbery in January 1871 in the tiny settlement of Gads Hill, Missouri, when Jesse, Frank and his gang stopped a train bound from St. Louis to Little Rock and robbed the crew members and the passengers at gun point. No one was killed or injured in the robbery; surprisingly, the actions of the robbers were later characterized as polite and considerate by two St. Louis newspapers, the St. Louis Daily Globe and the St Louis Post Dispatch. They reported that during the robbery, Jesse and his gang refused to take money from women, nor did they rob those men who obviously had a working class background. One robber was allegedly quoting Shakespeare as he relieved the passengers of their money and jewelry. And instead of robbing a minister on the train, they agreed to leave him alone if he would say a prayer for the robbers, which he did before the men jumped off the train and rode away on their horses.
The ongoing string of armed robberies continued until 1882, when Jesse was shot and killed by a relative. But it did not end the perception of Jesse James as the ultimate outlaw. Once Hollywood realized the commercial value of projecting Jesse as that ultimate outlaw, the legend was revived with vigor starting in 1908. According to Ted Yeatman in his book, “Frank and Jesse James”, there were 38 movies produced between 1908 and 1995 about the life and times of Jesse James. And believe it or not, here are some of the famous actors who played the role of Jesse in some of these movies: Tyrone Power, Roy Rogers, Clayton Moore, Dale Robertson, Audie Murphy, Robert Wagner, Robert Duvall, Kris Kristofferson, Rob Lowe and Sam Shepard. But the fascination with Jesse James did not end there. There was a 1995 movie entitled “Alias Jesse James” that featured the following supporting cast: Bob Hope, Gary Cooper, Bing Crosby, James Arness, Gene Autry, Roy Rogers and Fess Parker. Obviously, this was not a movie that dared to suggest that Jesse was a thug.
And no list of Hollywood movies running a theme into the ground would be complete without these two gems: “Jesse James Meets Frankenstein’s Daughter” and my favorite (without ever seeing it), “The Outlaws and the Three Stooges”, staring—you guessed it—the Three Stooges.
Note: Brother Frank turned himself in to authorities after Jesse was killed. He was tried twice for murder and was acquitted both times. He later became a celebrity in a “Wild West Show” and in his final days, a tour guide at his family farm in Missouri.
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■ Bill Hoagland has practiced law in Alton for more than 50 years, but he has spent more than 70 years hunting, fishing and generally being in the great outdoors. His wife, Annie, shares his love of the outdoor life. Much of their spare time is spent on their farm in Calhoun County. Bill can be reached at [email protected].