Jesse James & The Adair Train Robbery

Jesse James

The Civil War taught Jesse and Frank James a lot more than how to fight. It taught them how to rob, plan, and disappear. By 1873, they’d turned those wartime lessons into a cold, professional craft—bank robberies, stage holdups, and the occasional daylight shootout. Yet none of it compared to what happened on the night of July 21, 1873, along the lonely rails outside Adair, Iowa.

It was the first successful robbery of a moving train west of the Mississippi River. The Reno brothers in Indiana had done it seven years earlier, but Jesse and Frank were about to take it to another level.

Before Adair, the James-Younger Gang had tried their hand at a few banks. None paid off like they’d hoped. In Ste. Genevieve, Missouri, they expected $100,000 and left with less than $4,000. At Gallatin, they killed a cashier, nearly got killed themselves, and rode off with a pitiful $700. Jesse was tired of small change. This time, he promised, would be different.

He sent Frank and Cole Younger north to Omaha to scout a shipment of gold and silver—bullion from Cheyenne bound east. Meanwhile, Jesse, Clell Miller, Bill Chadwell, Jim Younger, and Bob Younger waited in the Iowa hills near Adair. The plan was bold and brutal: derail the train, rush the express car, and vanish before the law could even telegraph their names.

No one’s certain how Frank and Cole learned the train’s schedule, but word came that the bullion would pass through Iowa on July 21. Modern historians believe their intelligence was off—Jesse may have robbed the wrong train, missing the real shipment by a day. Either way, the gang wasn’t turning back.

The Atlantic Express left Council Bluffs that evening at 4:55 p.m., bound east on the Chicago, Rock Island & Pacific line. Four coaches, two sleeping cars, and an engine pulling a tinder car. Among the passengers were thirty upper-class Chinese students traveling to Springfield, Massachusetts. In the express car sat $2,000 in cash, a pile of mailbags, and—though the outlaws didn’t realize it—three tons of gold and silver bars sitting right on the floor.

Frank James

Earlier that day, Jesse’s men broke into a section house, stealing a spike maul and a crowbar. They pried loose the iron spikes on a curved stretch of track three miles outside Adair, tied a rope to the loosened rail, and hid in a ditch. When they heard the whistle, they pulled. The rail ripped free.

At 7:39 p.m., the train steamed through Anita at 25 miles an hour. Moments later, Engineer John Rafferty spotted the break—but too late. He slammed on the brakes and threw the engine into reverse. The locomotive and tinder tore off the track, tumbling down an embankment. Rafferty was crushed to death instantly.

Conductor Billy Smith, dazed and half-deaf from the crash, stumbled outside. Shots cracked around him. He thought the bandits were firing at random until two bullets sliced through his jacket. Nearby, fireman Dennis Foley crawled from the wreck, whispering, “Jack’s dead.” He had carried Rafferty’s lifeless body clear of the boiler, terrified the wreck would explode.

Then six men appeared, their faces masked in white cloth, “Ku Klux style.” They moved like soldiers, firing warning shots, shouting orders. “Get out of there, damn you! Get out of there!” Bullets riddled the express car. Messenger John Burgess felt one graze his scalp. Another nicked his partner’s head.

Three robbers burst through the door. One yanked off his mask. The witnesses later swore it was Jesse James—“red-faced, sandy-haired, five foot seven, well-built, with a vicious countenance.” He shoved a revolver in Burgess’s face. “Give me those keys, goddamn you! Give us the money or I’ll blow your brains out!”

Burgess opened the safe. Jesse scooped out $2,000 in bills but wasn’t satisfied. He kept demanding “the bullion,” not realizing the silver and gold bricks he stepped over were exactly that. “We don’t want them things,” he snapped. His ignorance cost him $50,000.

Outside, the other bandits paced the train, waving pistols and shouting at passengers to stay inside. Ten minutes after the wreck began, it was over. The gang melted into the darkness, crossing the open prairie to where their horses waited.

Route agent O.P. Killingsworth later gave the best account of what happened inside. “The express car was lifted, turned, and shoved forward,” he said. “We were tossed about with packages, bullion, and mailbags crashing into us.” When the masked leader entered, Killingsworth noticed he moved with confidence—too confident for a random bandit. “He tore off his mask,” Killingsworth recalled, “and gave orders like a commander.”

By midnight, Superintendent H.F. Royce had walked four miles to find a handcar, then rode another eight to the nearest telegraph office. Within hours, word flashed across Iowa. Two special trains left Omaha loaded with armed men and horses. By dawn, 500 men were in the field, scouring the countryside for the robbers. They found nothing.

Jesse James on horseback, overseeing his men

A week later, the St. Louis Republican reported the fugitives had crossed the Hannibal and St. Joe Railroad near Chillicothe, Missouri, trailed by a posse just three miles behind. Then the trail went cold. When authorities raided the Younger family home that September, they found only women and children.

By August, the Daily Morning Herald of St. Joseph declared the truth: Jesse James would never be caught. He had too many friends in Clay and Jackson counties—former rebels who still saw him as a hero. A month later, the Chicago Tribune warned that “the robbing of trains west of the Mississippi has become a regular profession.”

They were right. Adair wasn’t just a heist—it was a beginning. From that Iowa hillside, Jesse James and his gang wrote the next chapter of American outlaw history, with pistols, rail spikes, and the promise of easy money.