9 Wild West Outlaws Who Wreaked Havoc Across The American Frontier

Published September 5, 2022
Updated May 14, 2025

Jesse James: The Confederate Guerrilla Turned Wild West Outlaw

Wild West Outlaw Jesse James

Library of CongressA young Jesse James.

Like many Wild West outlaws, the life of Jesse James was shaped by the Civil War. Born on September 5, 1847, in Clay County, Missouri, Jesse James was just a young teen when the conflict first broke out in 1861.

Though Jesse was too young to enlist, like his brother Frank James, the Civil War soon showed up at his doorstep. According to PBS, Union militiamen came to the James’ home and roughed up Jesse and his stepfather. Then, Jesse joined a Confederate guerrilla group led by “Bloody Bill” Anderson.

Jesse James — and his brother Frank James — joined Anderson on brutal raids against Union soldiers. In 1864, they participated in a raid on Centralia, Missouri, where guerrillas executed 22 Union soldiers in a “carnival of blood.” Shortly thereafter, Jesse and Frank James helped kill some 100 federal troops who were attempting to catch the guerrilla group.

But once the war ended, Jesse James didn’t hang up his guns. Instead, he and his brother formed the infamous James-Younger gang.

Last Photo Of Jesse James

Public DomainThe last known photo of Jesse James alive.

According to Biography, Jesse James and his gang wreaked havoc across the Wild West. They robbed more than 20 banks and trains, stole some $200,000, and murdered anyone who got in their way. While Jesse James often implied that his gang robbed to avenge the fallen South and to give their loot to the poor, there’s no proof they actually distributed any money.

In any case, Jesse James’ criminal ways soon caught up to him. Though he escaped capture during a foiled bank robbery in Northfield, Minnesota, in 1876, the failed heist resulted in the arrests or deaths of many of his gang members. Jesse and Frank James then started to associate with brothers Charlie and Bob Ford — but Bob Ford would betray Jesse James.

On April 3, 1882, Bob Ford, hoping to collect a $5,000 bounty, fatally shot Jesse James as the Wild West outlaw straightened a painting on the wall. In the end, Ford only got a fraction of the reward that he was promised.

author
Kaleena Fraga
author
A senior staff writer for All That's Interesting since 2021 and co-host of the History Uncovered Podcast, Kaleena Fraga graduated with a dual degree in American History and French Language and Literature from Oberlin College. She previously ran the presidential history blog History First, and has had work published in The Washington Post, Gastro Obscura, and elsewhere. She has published more than 1,200 pieces on topics including history and archaeology. She is based in Brooklyn, New York.
editor
Jaclyn Anglis
editor
Based in Brooklyn, New York, Jaclyn Anglis is the senior managing editor at All That's Interesting, where she has worked since 2019. She holds a Master's degree in journalism from the City University of New York and a dual Bachelor's degree in English writing and history from DePauw University. In a career that spans 11 years, she has also worked with the New York Daily News, Bustle, and Bauer Xcel Media. Her interests include American history, true crime, modern history, and science.
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Fraga, Kaleena. "9 Wild West Outlaws Who Wreaked Havoc Across The American Frontier." AllThatsInteresting.com, September 5, 2022, https://allthatsinteresting.com/wild-west-outlaws. Accessed August 26, 2025.