Jesse James and Other Outlaws Who Got Away (Until They Didn’t)

by Mark Lee Gardner for Bookish.com

"The Americans are certainly great hero-worshippers, and always take their heroes from the criminal classes." Those are the words of Oscar Wilde, who chanced to arrive in St. Joseph, Mo., just days after outlaw Jesse James was assassinated by gang members Bob and Charlie Ford in the spring of 1882. Not all Americans worshipped Jesse, of course--especially not the owners of the banks and express companies the infamous outlaw targeted. But it is true that we have long had a fascination for outlaws that stretches all the way back to Robin Hood.

It should come as no surprise that both Jesse James and Billy the Kid, the most well-known Old West outlaws, have often been compared to Robin Hood, with many believing even today that Jesse and Billy robbed the rich to give to the poor. They didn't, but just like the Robin Hood tale, those American outlaws who were able to elude and humiliate their pursuers again and again have remained the most popular. Here are some outlaws who fought the law and won--well, at least once.

Jesse and Frank James

Via esl-bits.net

With their pals the Younger brothers, Cole, Jim and Bob, the Jameses were the quintessential horseback outlaws, raking in tens of thousands of dollars from banks and trains across the Midwest and South. Until September 7, 1876, the James-Younger gang had never been challenged, denied or defeated. But on that day, when they attempted a bank robbery in the small town of Northfield, Minn., everything that could go wrong did. The townspeople fought back, killing two gang members in the street. The Younger brothers were captured two weeks later, but Jesse and Frank eluded one of the largest manhunts in U. S. history and made it back to their Missouri hideouts. Following Jesse's death six years later, Frank turned himself in and was acquitted in two criminal trials. He subsequently lived for more than 30 years a peaceable citizen and died on the family farm near Kearney, Mo., in 1915.

Billy the Kid, a.k.a. William H. Bonney

On April 28, 1881, Billy the Kid, who had a well-deserved reputation as an escape artist, single-handedly killed his two guards with their own weapons, stole a horse and rode away unmolested from the courthouse jail in Lincoln, N.M. His brazen daylight escape is by far the most famous and astonishing jailbreak in the history of the Old West. A key to Billy's success was the absence of Sheriff Pat Garrett, who was away collecting county taxes that day. Many, even Garrett, thought Billy would flee across the border to Mexico. But he didn't. Billy had a sweetheart in Fort Sumner, N.M., where Pat Garrett finally caught up to him around midnight on July 14, 1881. In a darkened bedroom, Garrett shot Billy dead. The Kid was all of 21.

Butch Cassidy and the Sundance Kid

Source: AP file photo/Nevada Historical Society / Via thewesternonline.com

Butch and Sundance, who became outlaw icons with the tremendously popular 1969 Western starring Paul Newman and Robert Redford, really did flee to South America in 1901 with a mysterious woman known as Ethel or Etta Place. They had gone there to elude the detectives of Chicago's Pinkerton Detective Agency, who, armed with a recent photograph of the pair and their cohorts (the gang was known as the Wild Bunch), were slowly but surely closing in on the outlaws. But while Butch and Sundance were able to escape the Pinkertons, they could not escape their nefarious ways. They were killed on November 6, 1908, in a shootout with three Bolivian soldiers and local officials (not the army as portrayed in the movie) following their robbery of a mining company's payroll.

Bonnie and Clyde

Via en.wikipedia.org

Another duo made popular by a hit movie (this one starring Warren Beatty and Faye Dunaway), Bonnie Parker and Clyde Barrow were among the "Public Enemies" of the 1930s, a small group of deadly criminals that included John Dillinger and Pretty Boy Floyd. Bonnie and Clyde committed numerous robberies, at least a dozen of them banks, and Clyde even pulled off a notorious jailbreak for several inmates at the Eastham state prison facility in Houston County, Texas, in January, 1934. Worse, though, was the Barrow gang's cold-blooded killing of as many as nine police officers over a span of years. Bonnie and Clyde looked to be unstoppable. And in a way, they were, at least with normal police tactics. The only way law enforcement was able to end their criminal career was through a horrific ambush (law officers fired over 130 shots into their car) near Sailes, La., on May 23, 1934.

D. B. Cooper

Via wired.com

That's not his real name, which we'll probably never know. But on November 24, 1971, a man holding an airplane ticket with the name Dan Cooper hijacked a Boeing 727 jet, claiming he had a bomb. Cooper demanded $200,000 in cash, which he was given. Then, as his jet flew over the forests of the Pacific Northwest, Cooper strapped on a parachute and jumped from the plane at 10,000 feet--he was never seen again. Some of his ill-gotten money was, though. In 1980, three packets of the ransom cash, amounting to $5,800, were found along the Columbia River downstream from Vancouver, Wash. The money revealed no clues about Cooper's fate. Many, including the FBI, believe he died during the jump, but until his remains are discovered, or someone is convicted of the crime, D. B. Cooper has truly gotten away with it.

Mark Lee Gardner is the author of "Shot All To Hell: Jesse James, the Northfield Raid, and the Wild West's Greatest Escape," a nonfiction book from William Morrow. Mark's previous book for Morrow is the critically acclaimed "To Hell on a Fast Horse," which tells the story of Billy the Kid and Sheriff Pat Garrett. An authority on the American West, he has appeared on PBS's "American Experience" and ABC's World News, as well as on the History Channel, the Encore Westerns channel, NPR and BBC Radio. Mark lives with his family in Cascade, Colo.