Jesse James: The Confederate Guerilla & Notorious Outlaw

Post-Civil War outlaw Jesse James made a career out of robbing banks and trains of tens of thousands of dollars alongside other bandits in the James-Younger gang.

May 14, 2023By Amy Hayes, BA History w/ English minor
outlaw jesse james portraits
Portraits of young Jesse James (left) and Jesse before his death (right) by B.J. George Sr. and Photo & View Company Photographs, via State Historical Society of Missouri


Outlaw Jesse James was one of the most notorious bandits of the late 19th century. Alongside his older brother and various other gang members, Jesse James led the James-Younger gang in a series of bank and train robberies. His violent criminal streak began after the end of the Civil War when he served as a Confederate guerilla. Part of Jesse James’ criminal activity stemmed from his hostility toward Union soldiers who treated his family poorly during the war. Despite close encounters with law enforcement, the James brothers managed to escape the scene of their crimes. After more than a decade of committing various robberies, the chase for the James boys was put to rest when Jesse was shot and killed.


Outlaw Jesse James & The Civil War

Photograph of Jesse James (right), Frank James (center), and Charles F. Taylor (left) as Confederate guerillas by Richard S. Brownlee, 1864, via State Historical Society of Missouri


Jesse James was born on September 5, 1847 in Clay County, Missouri. He had three other siblings, one of which died in infancy. Jesse’s father, Robert James, was a well-known Baptist minister who owned a farm and enslaved people. When Jesse was three years old, Robert left his children and wife, Zerelda Cole James, behind to preach to gold miners in California. He never returned to Missouri and was believed to have died in 1850 at a gold mining camp due to cholera. Zerelda James was left to care for a handful of enslaved people, her children, and a 100-acre farm as a widow.


Jesse’s family were strong supporters of the Confederacy as the Civil War began. Jesse’s older brother, Frank James, joined the Quantrill’s Raiders to support the Confederate cause. The Quantrill’s was a pro-Confederate guerilla group that fought against Union soldiers in the war. Missouri held a neutral military position in the Civil War, but it became a hostile stomping ground due to its close proximity to both Union and Confederate states. Issues between the James family and Union soldiers began in the midst of the war as they appeared at the James farm. The soldiers harassed and threatened the James family in an effort to get information about the Confederate guerillas.


Frank joined Quantrill’s guerilla group led by William “Bloody Bill” Anderson in 1862. Jesse attempted to join the guerilla unit alongside his brother when he was 14 years old, but he was rejected due to his young age. Jesse offered support in other ways by becoming a spy for the guerillas instead before he was recruited by the guerillas unit the following year. Jesse James’ involvement in the Confederate guerilla band helped him adopt some of the strategies he would later use as an outlaw.


Jesse James Begins His Outlaw Career

Photograph of outlaw Jesse James (seated left) and Frank James (seated right) with Bob and Cole Younger (standing), via Library of Congress, Washington DC

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Shortly after Robert E. Lee’s surrender, outlaw Jesse James suffered a gunshot wound to the chest in May 1865 during a guerilla raid known as the Centralia Massacre. The raid resulted in more than 100 Union soldiers being injured and killed by Confederate guerillas. Jesse spent the next year recovering from his gunshot wound and then began his life as an outlaw. In February 1866, outlaw Jesse James committed one of his first robberies at the Clay County Savings Association. He shot a bystander and robbed the bank of around $58,000. It was one of the first armed bank robberies in the United States.


Jesse traveled to Russellville, Kentucky in 1868 with Cole Younger, Al and George Shepherd, and Jim White to commit another bank robbery. Part of the crew guarded the outside and intimidated bystanders, while the others held up the bank and managed to get away with $14,000. After spending two years away from the states in Mexico on the Rio Grande frontier, Frank and Jesse James traveled to Corydon, Iowa, along with other bandits, to rob a bank. They escaped with $40,000, and Cole Younger made a mockery of the robbery by interrupting a nearby political meeting to announce the robbery during their getaway. Most of the robberies the James boys committed were alongside the Younger brothers, which consisted of Cole, Jim, and John Younger. The group became known as the James-Younger gang, and other bandits occasionally joined in their heists.


James-Younger Gang Robberies

Display of guns and other equipment used by the James-Younger gang, via Library of Congress, Washington DC


The James-Younger gang traveled throughout the United States to commit their robberies. They were most notorious in Missouri and its surrounding states and the Midwest. In 1872, they continued their heists in Columbia, Kentucky. Only the James and Younger boys were identified as the culprits in robbing a bank and shooting a cashier. This raid wasn’t nearly as successful as the others, as they only got away with $200. During the 1870s, train and bank robberies became more frequent.


The gang took over a Chicago, Rock Island, and Pacific Railroad train and wrecked it. The bandits robbed the express messenger and rode away with $6,000. They committed a number of stage robberies around the Hot Springs, Arkansas area following the train heist. It seemed that little was being done to hunt down the James-Younger gang. The bandits were getting away with thousands of dollars in almost every robbery they committed, amounts that would be the equivalent of tens of thousands of dollars today.


Pinkerton detectives were employed to try and catch the outlaws in 1874. However, their efforts fell short, and plans to capture the gang members using Pinkerton services were abandoned two years later. One of the attempts to capture the James boys took place at their farm in Missouri. Pinkerton detective Joseph W. Whicher visited the James property undercover as a farm hand looking for work. The James boys were home at the time Whicher visited the farm. This would ultimately be Whicher’s downfall, as the boys immediately suspected him of being trouble. Jesse and Frank held Whicher captive. They dragged Whicher by horse to the nearby city of Independence in Jackson County, where they shot him in the head three times.


Proclamation issued by Governor Thomas T. Crittenden for the capture of any or all James-Younger gang members, via State Historical Society of Missouri


Deputy Sheriff Ed McDaniels hired James Wright and Captain Tull of the Chicago police to go undercover as cattle buyers in Cass County to catch the Younger brothers. Wright, Tull, and McDaniels found the Younger brothers, but they had been discovered. The Younger boys followed the men, and the encounter ended with a gunfight. John Younger murdered McDaniels, and Captain Tull managed to shoot John in the neck, causing his death. In the midst of this quarrel, Jim Younger was following Wright but returned when he heard the shots fired by Tull. Jim shot Tull and left him for dead. However, Tull was found later that night and taken to a nearby town to receive treatment. Captain Tull died six weeks later due to his injuries.


New bandits joined Frank and Jesse James in a series of robberies in the mid-1870s. In December 1874, outlaw Jesse James robbed a Kansas Pacific Railroad train with the help of Clell Miller, Bud McDaniels, Jim Hinds, and Thompson. The group got away with more than $24,000 cash and a large amount of fine jewelry on its way to New York. McDaniels was arrested just days later, and some of the jewelry stolen on the train was found on him.


The gang targeted the Missouri Pacific Railroad in the summer of 1875. This heist consisted of Frank and Jesse James, the Younger brothers, Clell Miller, Charlie Pitts, Hobbs Kerry, and Bill Chadwell. Chadwell was a known horse thief outlaw from Minnesota. The gang managed to rob the train of $15,000 and then made their way to Huntington, West Virginia, where they stole $6,000 in another robbery.


The Northfield Bank Robbery

Photograph of the First National Bank in Northfield, Minnesota, via Northfield Historical Society


In August 1876, the James-Younger members, including Cole, Jim, and Bob Younger, Clell Miller, Charlie Pitts, Chadwell, and the James boys, traveled to Minnesota to stake out their next robbery location. The following month, the gang robbed a bank in Northfield, Minnesota. Although the James brothers managed to get away, Northfield was one of their most unsuccessful heists. The Younger brothers were arrested and sent to prison, and Pitts and Chadwell were killed by armed citizens. The James brothers were forced to flee the area. They spent some time in Nashville, Tennessee under fake identities. Frank’s fictitious name was B.J. Woodson, and Jesse’s alias was Thomas Howard.


Missouri Governor Thomas T. Crittenden issued a proclamation for the arrest of Frank or Jesse James in 1881 and a $5,000 reward for each bandit. The two brothers lay low for the next couple of years to avoid being captured. Jesse settled down with some family in St. Joseph, Missouri under his alias as a cattle buyer. However, his outlaw career wasn’t over. He recruited two new gang members, Robert and Charley Ford, to plan future robberies.


The End of Outlaw Jesse James

Photograph of dead outlaw Jesse James by R. Uhlman, 1882, via Library of Congress, Washington DC


Unbeknownst to Jesse, Robert Ford was working with Governor Crittenden to receive a reward for Jesse’s life. On April 3, 1882, Robert took his opportunity to shoot and kill Jesse James. Robert was tried for the murder of Jesse and found guilty. He was sentenced to death by hanging, but Crittenden pardoned him. The series of robberies and murders that took place across at least six states throughout the James-Younger gang’s criminal career was finally put to an end. The robberies took part in the devastation of Missouri’s economy and its surrounding states. Homesteaders who may have been interested in settling down in Missouri to start new businesses were reluctant to do so for fear of the notorious bandits.


Six months after the death of Jesse James, Frank James went to Governor Crittenden’s office to surrender himself on October 5, 1882. Frank James was put on trial for just two of the robberies and murders the James-Younger gang committed, a train robbery in Winston and a bank robbery in Gallatin, Missouri. His trial began on August 21, 1883 in Gallatin. Much of the evidence against Frank was circumstantial and didn’t hold up strongly. It only took the jury about three and a half hours to deliberate before they made their decision.


Frank James was acquitted of all charges against him. After his release, Frank abandoned his outlaw life for a number of odd jobs until he died on February 18, 1915 at the age of 72. Cole and Jim Younger served 25 years in prison and were released on parole in July 1901. Jesse James became the most well-known outlaw of the gang and has been referenced in various types of media, such as artworks, books, movies, and songs throughout the decades.

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By Amy HayesBA History w/ English minorAmy is a contributing writer with a passion for historical research and the written word. She holds a BA in history from Old Dominion University with a concentration in English. Amy grew up in the historic state of Virginia and quickly became fascinated by the intricate details of how people, places, and things came to be. She specializes in topics on American history, Ancient and Medieval England, law, and the environment.