Jesse James: Rise of an American outlaw

The violence of the U.S. Civil War transformed Jesse James from Missouri farm boy to vicious killer.

Murderer and thief, Jesse James was heavily armed when he posed for this photograph in the 1860s.
Photograph by Bridgeman / ACI

In the words of the popular 19th-century ballad “Jesse James, ” the infamous Missouri outlaw "was a man that was knowed through all the land. For Jesse, he was bold and bad and brave." And, to a certain extent, Jesse James was all those things.

In the dozen years from 1869 to 1881, Jesse James may have taken part in as many as 19 robberies—banks, trains, and stagecoaches—stretching from Mississippi to West Virginia to Minnesota. Nearly 20 people died as a result, including seven of Jesse’s cohorts, yet the brazen holdups continued. Law enforcement and private detectives failed repeatedly to corral Jesse and his gang, and Missouri earned the epithet the “Robber State.”

But before there was the bold and bad and brave Jesse, and long before there was the mythic Jesse of song, dime novels, and films, there was a blue-eyed boy, son of a Baptist minister and a devoted mother, coming of age in a land torn apart over slavery and divided loyalties.

Jesse’s parents, Kentucky natives, met in the summer of 1841. His father, Robert, was a student at Georgetown College. His mother, Zerelda Cole, attended a Catholic school in nearby Lexington. A classmate remembered Robert as exceptionally bright, but “his awkwardness and gawky appearance caused him to be the victim of many practical jokes.” The easy-going Robert took the jokes in stride, however, and soon be- came one of the most well-liked men at the college. Zerelda seemed to have discovered Robert’s charms as well, and they were married in December. The groom was 23 and his bride was 16.

On a trip to visit Zerelda’s mother and stepfather in western Missouri the next year, the couple liked the fertile country, and the frontier could always use another man of God. Leaving Zerelda in Missouri, Robert returned to Kentucky to complete his coursework, graduating with a bachelor’s degree on June 23, 1843 (he would earn his master’s five years later). When he reunited with Zerelda that summer, she greeted him with their first child: Alexander Franklin James. Robert purchased a 225-acre farm in Clay County, Missouri, and it was on that farm that Jesse Woodson James was born on September 5, 1847. A daughter, Susan, followed in 1849.

Growing Up

The highly intelligent, once awkward college student became a powerful presence in the region. When Robert became pastor of the New Hope Baptist Church, its membership stood at 20; seven years later, that number had grown to almost 300. In 1849 he was a founding trustee of William Jewell College in Liberty, Missouri, which operates to this day. But in 1850, Robert chose to leave his family and parishioners behind to join a party of Clay Countians bound for California. Since the discovery of gold there two years earlier, dreams of quick fortunes had lured thousands over land and by sea to the new El Dorado. For Robert James, though, an even greater dream may have been the saving of men’s souls.

A story handed down in the family tells how little Jesse clung to his father and begged him not to leave. Once on his westward journey, Robert dutifully wrote home. “Give my love to all inquiring friends,” he ended one letter to Zerelda, “& take a portion of it to yourself & kiss Jesse for me & tell Franklin to be a good boy & learn fast. I must close by saying live prayerful & ask god to help you to train your children in the path of duty. Fare-ye-well till my next letter.” That fall, those loving letters stopped. Robert James had succumbed to an unknown illness in a California mining camp.

Despite the severe hardship of Robert’s death, and a brief second marriage to a man who was not fond of the children (he died after falling from his horse), Zerelda made sure that Jesse James and his siblings were well taken care of on the family farm—and that the farm remained under her control. She went so far as to insist on a prenuptial agreement with her third and last husband, Reuben Samuel, a doctor and fellow Kentuckian, whom she married in 1855.

The woods and fields of Clay County were the James boys’ playground, but there was a dark underside to life at that time and place. Slavery was everywhere in western Missouri, with its numerous tobacco and hemp farms. Clay County counted 2,742 slaves in 1850, and six of those belonged to Reverend James (Robert sold a young slave to help finance his trip to California). Only one of those six was an adult, a 30-year-old woman named Charlotte, whose work was likely confined to household chores and caring for the children, both free and enslaved.

The James Brothers’ Civil War

Although living less than 40 miles from the Kansas border, Jesse’s family was fairly insulated from the violence over whether the Kansas Territory would enter the Union as a free or a slave state. The outbreak of the Civil War in 1861, however, was another matter. “The people were all mixed up and Everybody was a spy for his side,” Frank James recalled about the atmosphere in Clay County during the war. “You were for the South and your neighbor was for Lincoln.” As slave owners with Kentucky roots, there was little question which side Jesse’s family would take. A neighbor recalled that when news of the war came, 18-year-old Frank James “was wild, shooting his pistol and hallooing for Jeff Davis.”

Jesse was far too young to enlist. Frank joined the pro-Southern Missouri State Guard and in less than five months’ time fought in two major Missouri battles, Wilson’s Creek and Lexington, both Confederate victories. But that winter he was a patient in a military hospital, laid low not by a bullet but by measles. Captured by Federal forces, Frank was subsequently paroled and sent home, bound by an oath not to take up arms again against the Union. Yet as the war in Missouri devolved into bloody atrocities and reprisals, it was impossible for any able-bodied young man to stay out of the fight.

In May 1863 Frank joined the command of Southern guerrilla leader William Clarke Quantrill. The guerrillas, also known as bushwhackers, acted as irregular cavalry, generally operating independently of the Confederate army and devising their own objectives as their leaders saw fit. They supported themselves through raiding and help from their kin, which is why Federal militia appeared at the James farm soon after Frank joined the guerrillas.

The militia believed Frank was hiding nearby with other bushwhackers and ordered young Jesse to tell them where they were. When Jesse refused to talk, the soldiers mercilessly beat and whipped him. Next they tortured Jesse’s stepfather, Reuben Samuel, stringing him up by the neck until the poor man agreed to lead them to the bushwhacker camp. The militia had not come to take prisoners and immediately opened fire on the guerrillas, killing two of them. Frank ran like hell, barely escaping as bullets whizzed around him. “After that day,” Frank would recall years later, “Jesse was out for blood.”

But Jesse’s vendetta ride would have to wait until the next year. He was only 15 and, more importantly, a valuable tobacco crop on the family farm required tending. Jesse raised and harvested that crop with the help of a slave. The following winter months found most of the Missouri guerrillas encamped in Texas, but they were back in the spring and looking for recruits. Crops or no crops, nothing was going to stop Jesse from enlisting this time. Like his big brother Frank before him, he “went to the brush.”

The James boys began exacting their revenge in June 1864. Accounts vary, but Jesse is reported to have killed Brantley Bond, one of the militiamen who had whipped him and hanged his stepfather. Bond surrendered to the bushwhackers and begged for his life, but Jesse, the story goes, reminded Bond of his deeds and then shot him dead. Another militia member, Alvis Dagley, was found the next day working in a field near his home. The guerrillas marched him to the road, where Frank put a bullet in him. “We did burn the houses of Yanks,” Frank admitted years later. “We shot spies. So does everybody. If we hadn’t we wouldn’t have lasted a week.”

Jesse was wounded twice that summer. The more serious of the two injuries came when he tried to steal a seemingly unattended saddle. The saddle’s owner, a German Unionist farmer, saw what was happening and got off a quick shot from the doorway of his home, hitting the young thief in the right chest. Jesse didn’t need a saddle for the next few weeks. The second wound occurred as Jesse was cleaning one of his revolvers. The gun suddenly went off, blowing away the tip of the middle finger on Jesse’s left hand.

As blood squirted everywhere, Jesse cried, “O, ding it! ding it! How it hurts!” From that day forward, Jesse James was known to family and close friends as “Dingus.”

September found Jesse and Frank riding with guerrilla leader “Bloody Bill” Anderson, whose men became infamous for taking the scalps of dead enemy soldiers. On the 27th, Anderson’s bushwhackers sacked the town of Centralia, Missouri, and murdered 24 Federals on furlough who had the misfortune of being on a train that arrived at the depot during the mayhem. Later that day, Anderson’s guerrillas routed a force of 115 Federals that had come in pursuit of the bushwhackers. Jesse, on a fleet horse at the head of the charge, galloped to within a few feet of the Union commander and knocked him out of his saddle with a pistol shot to the head. Only a handful of the Federals survived.

Jesse’s feat would become famous, but Centralia would be the bushwhackers’ last bloody hurrah Anderson died in a skirmish with militia the next month. After another winter in Texas, the guerrillas returned to Missouri in the spring for more looting of towns and killing of Unionists, but the Confederacy was finished. So was Jesse’s part in the war. In a May 15 firefight with a Federal patrol near Lexington, Missouri, a pistol ball ripped through Jesse’s right lung, in nearly the same place as his wound of the previous year. This time, however, the injury nearly killed him.

Jesse’s family claimed he was on his way to surrender when his party was attacked. Regardless, surrender he did after being wounded again. A week later, as he lay on a Lexington hotel bed slowly recuperating from the gunshot, Jesse James swore his allegiance to the United States. Brother Frank surrendered in Kentucky on July 26.

After the War

Jesse’s injury required several months to fully heal. When he returned to Clay County, he found many of his Unionist neighbors weren’t willing to let bygones be bygones. So, too, the Radical Republicans who made up the Missouri legislature. They drew up a new state constitution in 1865 that forbade slavery. It also forbade any citizen from voting, holding public office, or teaching school unless they took the notorious “Ironclad Oath.” This pledge was entirely different from the oath of allegiance required of former Rebel soldiers. A person taking the Ironclad swore that he or she had never fought for, supported, or even sympathized with the South. Because former guerrillas and their families could not legitimately make that pledge, they were, for a time, left with no voice or place in postwar Missouri.

Not unlike their old leaders Quantrill and Bloody Bill, a few of the disenfranchised chose to make their own rules. On February 13, 1866, 10 to 12 men rode into Liberty, Missouri, and robbed the Clay County Savings Association of $60,000 in gold, currency, and government bonds (largely the savings of Unionists) and shot dead a bystander. The local newspaper reported that the robbers were believed to be “a gang of old bushwhacking desperadoes. ”Jesse wasn’t involved in the holdup, but brother Frank likely was, along with another former guerrilla by the name of Cole Younger.

Why the Jameses and Youngers took up banditry following the Civil War when thousands of their fellow soldiers returned to their homes and pursued peaceful occupations has always been a question. The answer endlessly put forth by Jesse and Frank was that their enemies wouldn’t allow them to resume their old lives. “[M]y life was threatened daily,” Jesse later told a journalist about his return to the Clay County farm, “and I was forced to go heavily armed.” Frank argued, “We had as much chance of settling down, tilling our farms and being decent as a tallow dog chasin’ an asbestos cat through hell.”

Another answer Jesse and Frank might have given, perhaps one more readily believed, was that robbing banks and trains was easy money, and they were good at it.

Jesse’s First Robbery

There are many robberies in which Jesse was named as a participant, but hard evidence of his participation is often as elusive as the outlaw was himself. The first bank job in which Jesse James can positively be identified came three years after the Liberty affair, although the “robbery” may have actually been a planned assassination. On December 7, 1869, two men entered the Daviess County Savings Association in Gallatin, Missouri, killed the cashier for no apparent reason, and then grabbed a small metal box and fled. One of the robbers’ horses threw its rider, forcing the two to escape on a single mount. During their flight through the country, the robbers boasted to more than one person they met how they had slain Gallatin resident Maj. Samuel P. Cox. Cox was the commander of the militia that had killed Bloody Bill Anderson, and he was targeted so as to avenge their former leader.

Unfortunately for the dead cashier, it was a case of mistaken identity. Instead of Cox, the robbers had killed John W. Sheets. There was no mistake, however, in identifying the fine mare abandoned by the bandits: It was a champion racehorse named Kate, and its owner was one Jesse James.

A grand jury indicted both Jesse and Frank James for the murder of John W. Sheets the following May, prompting Jesse to write to the state’s governor to defend his case. In his letter, Jesse denied that he or Frank had anything to do with the holdup, and he assured the governor that he could prove his whereabouts on the day of the robbery by “some of the best men of Missouri.” “Governor,” he continued, “when I think I can get a fair trial, I will surrender myself to the civil authorities of Missouri. But I will never surrender myself to be mobbed by a set of bloodthirsty poltroons.”

Jesse James, age 22, was now an outlaw. Over the next 12 years there would be more hard riding, more robberies and more innocent victims, more letters denying involvement, and more offers of surrender in return for the guarantee of a fair trial. Jesse, his brother Frank, and their brothers in crime became the most wanted, the most despised, and the most celebrated outlaws in the nation. But on a spring day in 1882, Jesse’s run finally came to an end. With the promise of a large reward from Missouri’s governor, gang member Robert Ford fired one momentous shot into the back of the outlaw leader’s skull.

But the bullet that killed Jesse James had been fired years before Ford pulled the trigger on his revolver. While still a youth, Jesse’s life was dramatically upended by the violence of a horrendous civil war, which in turn had been brought about by the tragedy and violence of slavery. Like his fellow bushwhackers, many of them teenagers as well, Jesse became numb to the bloodshed and fixated on revenge. He killed men, and men tried to kill him. He learned to steal and pillage, justifying his actions with his own skewed moral code. Such are the things that make an outlaw.

Newspaperman and James brothers’ defender John Newman Edwards conceded that Jesse and Frank were “bad citizens.” But, he explained, “they are bad because they live out of their time.” More than 150 years later, Jesse James seems to have escaped time altogether, for the life and deeds of the Baptist minister’s son turned outlaw appear to be forever etched in the American consciousness.

Mark Lee Gardner, a Missouri native, is an award-winning author and historian living at the foot of Colorado’s Pikes Peak. He is currently writing a dual biography of Lakota leaders Crazy Horse and Sitting Bull.

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