Exterior of the First National Bank, Northfield, Minnesota

Based solely on longevity, Jesse James was one of America's most successful bank robbers; he eluded authorities for nearly 15 years. But in other respects, the operations didn't always go according to plan, as demonstrated by the very first robbery with which Jesse was publicly linked.

Gallatin
America's first daytime bank robbery during peacetime happened in the small town of Liberty, Missouri, on February 13, 1866. Bandits pistol-whipped a cashier at the Clay County Savings Association and made off with almost $60,000 in bonds, paper currency and gold and silver coin. The culprits, who got away after killing a passer-by, were assumed to be ex-bushwhackers, and the James brothers may have been among them. But Jesse's first publicly confirmed bank robbery wasn't nearly so lucrative, perhaps because its objectives weren't entirely financial.

Shortly after noon on December 7, 1869, Frank and Jesse James walked into the Daviess County Savings Association in Gallatin, Missouri. There were two men inside the modest one-story building; the bank cashier and a lawyer named William McDowell. One of the robbers, possibly Jesse, walked up to the cashier and asked to have a $100 banknote changed. As the cashier wrote out a receipt, the robber drew his revolver and fired two shots, one into the man's chest and another into his forehead. As McDowell ran for the door, he was shot in the arm. Jesse grabbed a portfolio of bank paper and raced outside. He and Frank rode out of town pursued by a posse, but they eventually escaped. The Gallatin robbery set the pattern for others to come. It was daring. It had motives beyond simple robbery, in this case the killing of the man who had hunted down Jesse's fellow bushwhacker "Bloody Bill" Anderson during the Civil War. It demanded attention. It resulted in the death of unarmed civilians. And it didn't go according to plan. In this case Jesse had snatched a collection of worthless paper from the bank, and the man he killed wasn't the intended target.

Croydon
But these failures didn't stop Jesse, and future robberies bore many of the same hallmarks as Gallatin. In June 1871, he and members of his gang robbed a bank in Croydon, Iowa, arriving during a speech by noted orator Henry Clay Dean that had drawn most of the town to the local Methodist church. Not content with stealing $6,000, the bandits went to the church and "shook the stolen money at the crowd," furious at being upstaged. The publicity-seeking continued when Jesse turned his attention to railroads; he left behind press releases boasting of the crimes. Another part of the Gallatin pattern was on display during an April 1872 robbery in Kentucky; the lead robber walked into the bank, said "good evening" to the unarmed cashier, and promptly shot him down. The Kentucky robbery netted little, as the mortally wounded cashier refused to open the bank vault. But whether he made much money or not, each robbery seemed to give Jesse a taste for more. In 1876, that taste would lead to his boldest expedition yet.

Northfield
Once again, Jesse's gang selected a bank for more than financial reasons. Northfield, Minnesota, was the new home of Mississippi's former Republican governor and former Union general Adelbert Ames, and he was a major depositor at its First National Bank. After two weeks of reconnaissance, eight bandits rode into Northfield on the afternoon of September 7. Then they split up: three waited by a nearby bridge, two others guarded the town square, and three more (including Jesse) walked into the bank. Once inside, they climbed over the counter, ordering the three employees to their knees. When the bank's bookkeeper told them the safe in the vault was on a time lock and couldn't be opened, they held a Bowie knife to his throat and cracked his skull with a pistol butt. But citizens outside had noticed the outlaws and begun arriving with guns. As shots rang out, Jesse and his comrades had to retreat. Several members of the gang would be cut down, others captured; in the end only Jesse and Frank would make it back the 500 miles to safety in Missouri. Their most ambitious operation ended in the greatest disaster. But before they left the bank that day, one of them, Frank or Jesse, did the one thing that more than any other defined their life of crime; he raised his revolver and shot the unarmed bookkeeper dead.

Train Robberies
When the transcontinental railroad joined East and West in 1869, opportunities for train robberies multiplied. Train heists were a new and particularly dramatic type of crime: a group of armed men taking control of a train, the symbol of modern life. It was a smart way to rob, since the perpetrators could pick their location, always somewhere remote, far from any pesky lawmen. The James gang was shrewd about the financial benefits and switched to robbing trains, for the most part, in the 1870s. They caught cash shipments on the move, usually emptying the safe in the express car and leaving passengers alone, which helped their image with the public.

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Since 1921, dozens of movies have featured a character based on Jesse James, depicting him in very different lights. Which portrayal do you think is the most historically accurate? Do you have a favorite?