The shot came from behind, fired while Jesse James stood on a chair adjusting a picture frame in his own home. Robert Ford, a young man who had joined the outlaw’s inner circle, pulled the trigger on April 3, 1882, collecting the $10,000 bounty that Missouri’s governor had placed on the notorious bandit’s head. Jesse James was 34 years old. The man who had terrorized banks and railroads for nearly two decades was dead, but the legend was only beginning to take shape.
Jesse James was born on September 5, 1847, in Clay County, Missouri. His father, a Baptist minister, died during the California Gold Rush when Jesse was just three years old. During the Civil War, Jesse and his brother Frank rode with Confederate guerrillas under William Quantrill and “Bloody Bill” Anderson, commanders known for their brutality along the Missouri-Kansas border. The war ended, but the violence did not.
On February 13, 1866, Jesse, Frank, and eight other men robbed a bank in Liberty, Missouri, escaping with $57,000 in the first daylight bank robbery in United States history. Over the next decade and a half, the James-Younger Gang pulled off more than 20 bank and train robberies, committed numerous murders, and stole roughly $200,000. The Pinkerton Detective Agency could not catch them, and for more than ten years the gang outran every lawman sent against them. The mythmaking began almost immediately.
A newspaper editor named John Newman Edwards, campaigning to return former Confederates to power in Missouri, wrote about Jesse James as a Robin Hood figure who stole from wealthy Yankee banks and gave to poor southern farmers. There was one problem: there is zero evidence Jesse ever shared a dime of his stolen money with anyone. His crimes hurt ordinary people as much as the rich. A little girl was shot in the leg during a botched robbery at the Kansas City Fair.
A train engineer was killed when the gang derailed his locomotive. Dozens of innocent bystanders were caught in the crossfire. The Robin Hood image was pure fiction. The beginning of the end came on September 7, 1876, when the gang attempted to rob the First National Bank in Northfield, Minnesota.
It was a disaster. Townspeople fought back, and of the $12,000 in the vault, the robbers grabbed exactly $26. Several gang members were killed or captured. Jesse kept going, but his circle was shrinking.
In 1881, the governor of Missouri posted a $10,000 reward for the capture of Jesse or Frank James. That bounty proved irresistible to Robert Ford. The aftermath was stranger than the crime career itself. Ford toured the country reenacting the killing, and audiences despised him for it.
Jesse’s mother charged tourists a quarter for pebbles from her son’s grave. Rumors spread for decades that Jesse had faked his own death. It was not until 1995 that scientists exhumed the body and used DNA from maternal relatives to confirm that Jesse James lay in that grave. A missing fingertip, the result of an accidental shooting while he cleaned his pistol, helped seal the identification.
His son later starred in two silent films about his father’s life in 1921, playing both himself and Jesse. Around the same time, in New Mexico Territory, another outlaw was building a legend that would outgrow even Jesse James. Billy the Kid, born Henry McCarty in 1859, has been portrayed in more motion pictures than any other single person ever. The real Billy was nothing like most portrayals.
He was slim, charming, fluent in Spanish, and popular with locals. He avoided drinking and smoking but loved singing, dancing, and gambling, especially cards. His first run-in with the law came at age 16 when he was arrested for stealing food and escaped jail by shimmying up a chimney. His real troubles began with the Lincoln County War in 1878.
After his employer, rancher John Tunstall, was murdered by men allied with a rival faction, Billy joined a group of vigilantes calling themselves the Regulators. On April 1, 1878, they ambushed and killed Sheriff William Brady in the street. The war climaxed in a five-day battle in Lincoln that July. The legend says Billy killed 21 men, one for each year of his life.
The truth is closer to four men he killed personally, with a hand in dispatching five others. Still plenty dead, but far from the myth. In December 1880, Sheriff Pat Garrett captured Billy. He was convicted of murder and sentenced to hang.
But on April 28, 1881, Billy wrestled a gun away from a guard, shot both deputies dead, and walked out of jail. The escape deepened his legend and sealed his fate. Garrett tracked him down and shot him dead on July 14, 1881, in Fort Sumner, New Mexico. For over a century, a single authenticated photograph misled people into thinking Billy was left-handed, because tintypes produce mirror images.
He was right-handed all along. That photograph sold at auction in June 2011 for $2. 3 million. A steady parade of newly discovered Billy the Kid photos has followed, and nearly all have been debunked, including a famous one supposedly showing him playing croquet.
One other figure from the Wild West deserves mention. Belle Starr, dubbed the bandit queen by the newspapers of her day, ran with outlaw gangs across Indian Territory in the 1880s, harbored rustlers and bandits, and became one of the few women of the era to earn her own wanted poster. She is often overlooked in favor of the male outlaws, but she formed a direct link between the Jesse James era and the outlaw women who would follow. Jump forward about fifty years to the Great Depression, and a different breed of outlaw captured the American imagination.
Bonnie Elizabeth Parker was born on October 1, 1910, in Rowena, Texas. She stood four feet eleven inches tall, weighed ninety pounds, and had strawberry blonde curls. Clyde Barrow was born March 24, 1909, in Ellis County, Texas. They met in January 1930 when Bonnie was 19 and still married to a man serving time for murder.
Over the next two years, the Barrow Gang robbed gas stations, restaurants, and small town banks across Texas, Oklahoma, New Mexico, and Missouri. Their biggest single haul was about $1,900, roughly $39,000 in today’s money. These were not criminal masterminds pulling off sophisticated heists. They were desperate, violent, and constantly on the run.
During their 21-month crime spree, gang members were responsible for 12 murders, most of them law enforcement officers. By the time of her death, there were no outstanding warrants against Bonnie Parker alleging murder, and there is very little reliable evidence she ever shot anyone. It did not matter. Texas Ranger Frank Hamer was on the trail, and on May 23, 1934, a team of officers set up an ambush on a rural road near Sailes, Louisiana.
They opened fire, and Bonnie and Clyde died in a hail of bullets. Tens of thousands of people lined up to view their bodies at separate funeral homes. The famous photo of Bonnie smoking a cigar was staged, a joke according to a wounded hostage she released, and she hated that image right to the end. Then there was John Dillinger, born June 22, 1903.
He became the most wanted man in America during a crime spree that lasted barely thirteen months, from June 1933 to July 1934. In that time, his gang robbed 24 banks and four police stations, and he escaped from prison twice. The most famous escape involved a fake gun he reportedly carved from a piece of wood shelving using a razor and darkened with shoe polish. He bluffed his way past guards and walked out the front door, a story backed up by a jail trustee he took hostage.
J. Edgar Hoover labeled Dillinger public enemy number one, and through him the FBI grew into a federal powerhouse. Pretty Boy Floyd was terrorizing the Midwest at the same time, and Machine Gun Kelly, whose real name was George Kelly Barnes, had just been captured after a high-profile kidnapping case that gave Hoover’s young bureau a badly needed public relations victory. Baby Face Nelson, whose real name was Lester Gillis, ran with Dillinger’s own gang and was arguably more violent than Dillinger himself.
Still, Dillinger slipped away, most spectacularly at the Little Bohemia lodge in April 1934, where agents botched the raid so badly that Dillinger escaped while an FBI agent was killed in the chaos. It took a tip from Anna Sage, a Romanian-born brothel madam facing deportation, to finally bring him down. She agreed to accompany him to the movies and wear a distinctive outfit so agents could spot him. She became known as the woman in red, even though she was actually wearing an orange skirt that night.
On July 22, 1934, FBI agents shot Dillinger dead outside the Biograph Theater in Chicago. An estimated 15,000 people filed past his body at the Cook County Morgue, and his gravestone has been replaced multiple times because visitors kept chipping off pieces as souvenirs. The outlaw era extends back west one more time with Butch Cassidy and the Sundance Kid. Robert Leroy Parker, born April 13, 1866, took the name Cassidy in honor of a cowboy mentor named Mike Cassidy.
Henry Longabaugh earned the name Sundance after a stint in Sundance, Wyoming. Together they led a gang called the Wild Bunch. When the law pressed in too close, they retreated to their hideout at Hole in the Wall, a remote canyon in Johnson County, Wyoming, so rugged that posses rarely dared follow. Their robberies were significantly more profitable than most.
They hit the San Miguel Valley Bank in Telluride, Colorado for $20,000, a Union Pacific train near Wilcox, Wyoming in June 1899 for somewhere between $30,000 and $60,000, another train near Tipton in August 1900 for about $55,000, and a train near Wagner, Montana in July 1901 for an estimated $40,000. With rewards climbing as high as $30,000, Butch and Sundance made a decision most outlaws never consider. They left. In early 1901, Cassidy, Longabaugh, and Sundance’s girlfriend sailed to Argentina and set up a ranch in Patagonia.
For a while, it seemed they had pulled off the ultimate escape. But old habits die hard. On November 7, 1908, two men believed to be Butch and Sundance were killed in a shootout with Bolivian soldiers. Or were they?
Members of Cassidy’s family always insisted he survived and came home. In 1991, forensic anthropologists tried to find and test remains in Bolivia but found nothing that matched DNA from living relatives of either man. The mystery may never be solved. The Dalton brothers followed a different path to infamy.
Grant, Bob, Bill, and Emmett Dalton started out as lawmen. Their older brother Frank, a federal deputy marshal, was killed by whiskey runners in 1887, and the surviving brothers pinned on badges in his honor. But somewhere along the way, they crossed to the other side of the law. By 1890, they had formed their own gang.
Bob Dalton reportedly declared the gang would beat anything Jesse James ever did by robbing two banks at once in broad daylight. On October 5, 1892, they tried exactly that in Coffeyville, Kansas. It was a bloodbath. Grant and Bob Dalton were killed, along with two other gang members.
Four townspeople died defending their city. Only Emmett survived, riddled with bullets. He was sentenced to life in prison, served fourteen and a half years as a model prisoner, received a pardon, and then moved to Los Angeles, got into real estate, wrote two books about his outlaw days, and even acted in a few movies. Every one of these outlaws lived fast, died young, or spent years in prison, and left behind a legend that grew far larger than the truth.
Jesse James never gave a penny to the poor. Billy the Kid killed four men, not 21. Bonnie Parker may have never fired a shot. Butch Cassidy might have died peacefully in bed somewhere in the American West decades after the history books said he was gone.
The people who actually lived through those times, the bank tellers, the train passengers, and the small town sheriffs, did not see Robin Hoods. They saw danger and death. The truth lies somewhere between the legend and the grave.