There have been a great many outlaws throughout the course of history, but most of them weren’t memorable enough for us to make note of them while the lived, much less a hundred years after their death. Some were interesting people who were thrust into a life of crime, others were less than admirable; either way, these are 15 of the most notorious outlaws and fugitives throughout recent history.
The Barefoot Bandit
We start this list off with the youngest and most recent of the bunch: Colton Harris-Moore a.k.a. “The Barefoot Bandit.” This 19-year-old kid has been all over the news lately for having finally been apprehended in the Bahamas (after a high-speed boat chase). He’s famous not just for his loathing of shoes, but also for his love of shenanigans and ability to elude the police for two years — going on the run at only age 17 after escaping from a halfway-house in Washington State. During his fugitive run, he’s believed to have stolen 5 planes, multiple automobiles, several boats, and cash from more than 100 robberies. He attributes his success to information available on the Internet, as well as the very well-written technical manuals that accompany most planes, cars and boats.
Frank Abagnale, Jr.
If the name seems familiar but doesn’t quite pop out at you, just think Catch Me if You Can and replace Leonardo DiCaprio with this guy — because the story was based on him. While he spends his time today living the high life as a security consultant and celebrity, he was a fugitive of epic proportions back in the 60s. At age 17, he managed to grab $2.5 million by passing forged checks to 26 different countries over the course of 5 years. In that time, he created at least 8 false identities and successfully impersonated an airline pilot, a lawyer, a prison inspector, and a doctor. It’s pretty obvious who Colton Harris-Moore’s role-model has been all this time, but it’s equally obvious that old Frank was a far better criminal.
In the dawning of the 20th century, Butch Cassidy was a man who robbed trains — and he did it well. He and his now-infamous gang, the “Wild Bunch,” pulled off dozens of robberies along the budding railways, nabbing thousands of dollars (just imagine the inflation rates). Butch, or as his mother knew him, Robert LeRoy Parker, made a smart move when he and his gang realized that the cops were gaining on them — he and his buddy, the Sundance Kid, fled to South America. While there are many versions of what happened to them after that, the one most widely-accepted is that they both died in a shootout over a mule in Bolivia, just a couple of years later.
While most outlaws have indeed been men, there have been a few notable women in the field. Belle Starr, born Myra Maybelle Shirley Reed Starr (now we understand the name choice), was a wild woman fit for the Wild West, and she earned herself quite the reputation in the post-war years of the late 1800s. She was a childhood friend of Jesse James, and ran in the same circles throughout her life. She was always, and we mean literally always, attached to outlaw men. One after another was gunned down, as she moved on to the next and continued on in her own stylish and brazen ways. While she managed to slip away from the cops (or bribe her way out of jails) for years, she was finally gunned down herself in 1889. That murder was never solved.
Bonnie and Clyde
No couple outside the realm of Shakespeare has ever attained the infamy of Bonnie Parker and Clyde Barrow. The handsome couple of outlaws left a trail of death everywhere they went, along with empty bank vaults, cash registers, and wallets. At one point they kidnapped a police chief. In 1934, after a 21-month-long spree of love and crime, Bonnie and Clyde were gunned down in their car after being ambushed by police in Louisiana.
Back in the days when the Internet was in its infancy and cable TV was still a luxury, John Gotti was America’s most famous modern outlaw. He had nicknames like “the Dapper Don” and “the Teflon Don” because of his debonair demeanor and his penchant for making charges brought against him slide right off. He was head of the Gambino crime family in New York City, and during the 70′s and 80′s that was a pretty rough time to be in any crime family in New York City. Unlucky for the Don, FBI monitors caught him on tape discussing crimes ranging from murder to tax evasion, and he was finally brought down. He died of cancer, in prison back in 2002.
Machine Gun Kelly
Born George Kelly Barnes, “Machine Gun” Kelly was a notorious and feared man during the days of prohibition. There was a lot of crime back in prohibition, but Kelly didn’t earn his name by hiding booze really well, he earned it by making gratuitous use of a Thompson submachine gun. Kelly and his gang bit off more than they could chew when they kidnapped a wealthy man from Oklahoma City. They got their $200,000 ransom, but the man was able to give enough information to the FBI upon his return that the gang was tracked down. Kelly was arrested, and spent 17 years in Alkatraz. He later died in Leavenworth on his 59th birthday, in 1954.
Our second Kelly on this list is Ned Kelly, and he was a different sort of criminal who lived in a different sort of land. In Victorian Australia, Ned Kelly and his gang ripped through the countryside while on the run from the police for a string of bank robberies. Instead of the usual run-and-hide methodology of escape, Kelly and the boys went all steampunk (appropriate to the era) and created hulking suits of iron armor made out of ploughs and whatever else they could get their hands on. When the police caught up to them, their bullets bounced right off Kelly and his men. Unfortunately, the suit wasn’t quite full-coverage, and Kelly was captured after getting shot in the leg. He was hanged in Melbourne in 1880.
Al Capone was, and likely remains to be, America’s most notorious and infamous outlaw. Back in the days of prohibition, he was considered the most feared man in America, and for people living anywhere within a hundred miles of Chicago, he was also the most powerful. Capone ran an empire of casinos, restaurants, hotels, and countless other businesses in the greater Chicago area that served as fronts for his equally vast empire of crime. He ran underground breweries and speakeasies, bootlegging routes, police precincts — you name it, he had a finger in it. The feds were unable to pin anything on him, despite the fact that everybody knew he was behind countless murders and other sorted crimes. In 1931, they finally got him on tax evasion of all things, and he spent 7 years in prison. He died shortly after release, in Florida.
Jesse James, easily one of the most recognizable names to come out of the fabled Wild West of the 1800s, was an outlaw who proved to be notoriously hard to kill. He and his gang began as Confederate guerillas, who because of their irregular status were branded as fugitives and war-criminals after the war. Wasting no time, he and what became the James-Younger gang started their decade-long spree of bank robberies, stagecoach hold-ups, railroad robberies, and general shenanigans and thievery. While always on the run, James managed to outsmart the law for years, but he was betrayed and shot by a fellow criminal for reward money in 1882.
Sam Bass and his gang were responsible for what is to this day the largest single robbery of the Union Pacific rail line. Bass hit the gold transport train while enroute from San Francisco, making off with $60,000 in gold (that’s about $1,194,276 in today’s dollars). Bass and his gang roamed about, performing robbery after robbery, until he was shot in a gunfight by a Texas Ranger in 1878. He was found dead in a nearby pasture later that very day.
John Dillinger was an outlaw who was loved almost as much as he was wanted. He was known for his polite, even friendly nonchalance while robbing people of everything they owned, and he once escaped from prison using a fake gun made out of wood (and that was just one of two jailbreaks). In the course of his spree, he robbed over two dozen banks, four police stations, and killed several policemen. He was smart, funny, deadly, and handsome, but he was betrayed by a local prostitute. She tipped off the authorities to his location in the hope that she wouldn’t be deported back to Romania, but after the cops ambushed and killed Dillinger, she was shipped back anyway.
Now 80 years-old — if he’s still alive — is the oldest man to ever make the FBI’s Ten Most Wanted list. James “Whitey” Bulger was added to the list in 1999 at age 69, and he’s been on it ever since. He was one of Boston’s most infamous gangsters, an Irish mob boss known for his ruthlessness, and the charges racked-up against him include murder, conspiracy to commit murder, extortion, conspiracy to commit extortion, money laundering, conspiracy to commit money laundering and narcotics distribution. That’s quite a list, and the old man still managed to get away.
Billy the Kid
A man of many names, Billy the Kid is as much legend as historical fact. He dove into crime at a young age, first arrested at around age 15 for stealing a basket of laundry. From there it was horse-theft, then cattle rustling, and finally to murder. He gambled and fought his way across the west, killing as many as 20 men in his short lifetime. He was caught a second time, but escaped from jail — only to be gunned down by a sheriff just months later in 1881.
Donald Eugene Webb has been on the FBI’s Top Ten list for longer than any other individual in history, and he’s still at large. His name was taken off the list in 2007 because authorities figured that the chances of his still being alive were slimmer than anybody actually catching him. Webb is wanted for killing a Pennsylvania police chief in 1980, after which he fled and managed to outsmart the cops at every turn. To this day, nobody knows where he is, or even if he’s still alive — but he was never caught.