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America’s 5 Favorite Old School Criminals

America’s 5 Favorite Old School Criminals

It’s no secret that criminals typically aren’t good guys. They rob trains, hold up banks, stick up average Joe’s, and do it all without any kind of fear of reprehension or guilt for their actions. Yet, the public always holds a peculiar preoccupation with the lives of these men (and sometimes women). There’s a certain level of romanticism attached to people so willing to break the rules and take chances. They’re exciting and dangerous, if even a little brave.

And while most criminals are feared for their reckless, wild behavior, there are a few stand-out, stand-up guys who are widely revered by the American public for their moral character (you know, outside of killing people or taking what doesn’t belong to them).

Here are 5 of America’s most revered criminals:

Jimmy Hoffa

Jimmy Hoffa was never officially outed as a legitimate gangster, but to say he had “friends in high places” all over the world would be an understatement. Hoffa found fame as an activist and labor organizer, and served as president of the International Brotherhood of Teamsters from 1958 to 1971. He helped literally thousands of the country’s hardest working men and women with their careers, and was known as the kind of guy who’d give a brother or sister in need the shirt off his back. He was a protector of working people everywhere. But in 1975, Hoffa mysteriously disappeared, and while a body was never found, several prominent mob hit men and associates have come forward throughout the years talking about who actually arranged the events that led to Hoffa’s death.

John Dillinger

We’ll be the first to admit that John Dillinger probably wasn’t the kind of guy who’d fund an orphanage or save a school bus full of kids from plunging off a cliff, sure. But the man makes our list because, for a thief, he was honest, compassionate, and as straight up as they come. He put his ass on the line to help bust fellow gangsters out of jail, he served in the U.S. Navy, and when the FBI put a $10,000 bounty on his head, people respected him enough not to snitch. In fact, Dillinger was so comfortable with not being ratted on that he went to professional baseball games, fancy restaurants, and movie theaters without any fear of being caught. That is, until Anna Sage, a woman whom Dillinger had been seeing, set him up with the FBI. He died in a hail of bullets (as any OG should), and over 10,000 people came to his funeral. You gotta respect a man who comes out swingin’ and goes down fightin’.

Theodore Roe

Teddy Roe was an African-American mob boss who made his cut in Chicago’s South Side during the 1940s and 50s. Roe’s lottery racket netted him millions of dollars a year, and when one of his partners was kidnapped by Sammy Giancana and the Chicago outfit, he paid the $100,000 ransom. When his partners fled the country, fearing Italian mob retribution, Roe refused to give in, knowing full well that his community needed him. In his South Side neighborhood, Roe was considered a black Robin Hood. He paid hospital bills, funeral tabs for the deceased, and invested a lot of his profits into legitimate businesses throughout the community. On several occasions, Roe had been known to walk through poor black neighborhoods, handing out stacks of 50-dollar bills.

He was considered an honorable crook by DEA and FBI agents, and even Giancana, who’d eventually order his killing, said it was a shame to kill such a great man.  

Charles Arthur “Pretty Boy” Floyd

Was he a murderous bank robber and a vicious killer, known for his recklessness with a Tommy gun? Absolutely. But Charles Arthur “Pretty Boy” Floyd, depression-era gangster and infamous bank robber, was also known to Oklahoma locals as “The Robin Hood of the Cookson Hills.” Perhaps more of a folk hero than notorious criminal, “Pretty Boy” Floyd would allegedly destroy mortgage papers (thereby freeing debt-ridden citizens) and could frequently be seen handing out stacks of stolen cash to random witnesses after hitting banks. In fact, when police would come looking for him, locals would turn their backs to protect Floyd from capture.

William Francis “Slick Willie” Sutton, Jr.

Probably the most relaxed bank robber of all time, Willie Sutton was an ardent pacifist and all-around good dude. He never killed anyone, used clever (and sometimes funny) disguises, and though he carried a Tommy gun into every single of the more than 100 banks he robbed, his guns were never, ever loaded.  In his over 20 years in lockup, Sutton would always help his fellow convicts, offering legal advice to anyone who would listen. Mob guys even loved him and looked out for him in jail because he was an honest, straight up, and completely non-violent gentleman. In an interview with Reader’s Digest shortly before his death in 1980, when asked if any of his guns were ever loaded, he said that he never carried a loaded weapon “because someone might get hurt.” It has also been alleged that Sutton would never rob a bank if women were screaming or babies were crying, probably because he felt too bad about it, which is actually the cutest shit ever.