Homage to An Outlaw

UPDATED 07/06/1992 at 01:00 AM EDT Originally published 07/06/1992 at 01:00 AM EDT

BACK WHEN JOHN DILLINGER, BABY FACE Nelson and Bonnie and Clyde roamed the land, aerating the scenery—and the occasional bank guard—with their trusty submachine guns, Charles Arthur "Pretty Boy" Floyd was the most fabled bandit of all. Described as a murderous "rat" by FBI director J. Edgar Hoover and given the title Public Enemy No. 1, he was gunned down from behind on Oct. 22, 1934, at age 30, after G-men caught up with him in an Ohio cornfield. But to the scores of aging relatives and friends who decorated Pretty Boy's humble grave-site with a colorful array of artificial flowers last month, he lives in memory as a genial mischief- maker who shared his spoils with dust bowl farmers in need. "Charley was fun to be with," says Mary Carlton, 80, his younger sister. "He always made me laugh."

For Pretty Boy's kinfolk, the reunion last month had an air of sweet vindication. In a new biography, Pretty Boy: The Life and Times of Charles Arthur Floyd, author Michael Wallis contends the Depression-era bandit was indeed something of a sagebrush Robin Hood who was generous to the farmers who gave him shelter and who delighted, during bank heists, in tearing up mortgages. According to Wallis, Pretty Boy pulled some 50 bank robberies and heists during a 10-year period and was implicated in one documented case of murder. On April 9, 1932, he shot Erv A. Kelley, a retired lawman turned bounty hunter who had trapped him in an ambush. But Wallis claims Floyd was wrongly accused by Hoover of participating in the Kansas City Massacre of 1933, a gangland shootout in which five people, including an FBI agent, were killed. "Charley was not the mad-dog killer he was portrayed to be," Wallis says.

Floyd was nicknamed Pretty Boy by a female admirer when he showed up at a poker game sporting a new suit and tie and hair slicked back with fragrant pomade. But his relatives insist he was cut from a different cloth than his flamboyant contemporaries, Bonnie Parker and Clyde Barrow, who killed at least 13 people during a bloody rampage through the Southwest in the '30s. Pretty Boy's nephew Jim Lessley, 56, who runs a café in Sallisaw, Okla., where clan members often congregate to tell stories, says Bonnie and Clyde came there several times, hoping Floyd would join up with them. "Don't tell them where I am," Floyd supposedly told his late brother E.W. "It's people like them that give bandits a bad name."

Not that Pretty Boy was an angel. On Nov. 1, 1932—All Saints' Day—practically the entire clan gathered in Sallisaw to watch him rob the local bank. His grandfather Charles Murphy Floyd took a seat of honor at the train depot, directly across from the bank. "My uncle and Grandpa had a joint savings account, and they lost their money in the crash of 1929," says Lessley. "Charley told Grandpa he was going to get the money back." On his way out of the bank Pretty Boy spilled some money and told his accomplices to leave it for the school-kids. Meanwhile, Grandpa Floyd was so busy jawing with his friends that he missed the whole show.

One of seven children raised by Mamie and Walter Floyd, a cotton farmer who made his own corn whiskey, Pretty Boy often played the fool as a boy. His sister Mary Carlton says he was especially fond of disgusting talk at the dinner table. "He would laugh while the rest of us became sick at our stomachs," Carlton says. Married at age 20 to Ruby Hardgraves, a long-legged, dark-eyed, part-Cherokee beauty, Pretty Boy dreaded spending his life behind a mule and a plow. In September 1925, eight months after the birth of his only child, Charles Dempsey "Jack" Floyd, he traded five gallons of moonshine for a pearl-handled pistol and stole $11,929 from a St. Louis payroll fund. Arrested a few weeks later, he did four years in a Missouri penitentiary. Following his release, Pretty Boy went on another crime spree and was sentenced to 15 years for an Ohio bank robbery but escaped by jumping from a train en route to prison.

Though Ruby had divorced Pretty Boy and remarried during his absence, she didn't hesitate to rejoin him when he showed up on her doorstep again in 1931. Jack Floyd, now 67 and a card club manager from Vacaville, Calif., who missed the recent family reunion while recovering from heart surgery, has never forgotten his secret first rendezvous with his father at age 6. "He smelled so good," Jack says. "I liked him right from the start."

Posing as a traveling salesman, Pretty Boy settled with Ruby and Jack first in Fort Smith, Ark., and later in Tulsa. Often he would disappear for weeks on end. "One day he said, 'Listen, I have a sack of coins out there and if you can bring it in, you can have it,' " Jack says. "It must have weighed 15 pounds. After I dragged it in, he said, 'Now hide it. When you want to take your friends out for an ice cream, you go right ahead.' " It wasn't long, though, before Jack's mother discovered his slash. "She took the money into town and bought me a suit and short pants," he says. "I hated that suit."

During his visits home, Pretty Boy was a doting dad. "When I was around 7 or 8, we went fishing and couldn't catch anything," says Jack. "So Dad got out his machine gun and said, 'You know what? We'll shoot 'em.' He let me pull the trigger. 'Well, we still didn't get any,' Dad said afterward. 'But we scared the hell out of 'em.' "

Pretty Boy was a soft touch when it came to discipline. One time when Jack angered Ruby by staying out after dark, Pretty Boy took him into the bathroom for a good whipping, but he hadn't the heart for it. "Dad whispered, 'When I hit this raincoat, you holler,' " says Jack. "I hollered like crazy and Mom tried to break down the door. 'I didn't mean for you to kill him,' she said. We never did tell her what happened."

In February 1932 Pretty Boy narrowly escaped a police dragnet in Tulsa, but Jack and Ruby were taken in for questioning and soon became the talk of the tabloid press. As Pretty Boy's notoriety continued to grow, further contact became extremely dangerous. In June 1933 an evangelist persuaded Ruby to put together a vaudeville show with Jack called "Crime Doesn't Pay." Mother and son went on the road as a secondary attraction at movie houses. "I'd come onstage in a blue blazer, white pants, and white shoes. I'd introduce Mom and she'd talk about the hard life," Jack says. "We went to some fine hotels, and I had my fill of raspberry sherbet, which was my favorite thing in the world. We heard that my dad came to see the show once, in a disguise, and really liked it."

Ruby and Jack gave their final show in September 1934. A few weeks later, Pretty Boy came home to Sallisaw—in a box. "We waited all night at the train station," Jack says. "I kept hearing the whistle blowing from far away, and I saw them unload the coffin." After stopping to wipe away a tear, Jack adds, "For years, every time I heard a train whistle, it reminded me of that sad night."

DAVID GROGAN
BOB STEWART in Sallisaw and CARLA MARINUCCI in Vacaville

Your Reaction

Follow Us

On Newsstands Now

Robin Roberts: How Loved Saved Me
  • Robin Roberts: How Loved Saved Me
  • Emma and Andrew: All About Hollywood's Cutest Couple
  • Prince George! More Yummy Photos

Pick up your copy on newsstands

Click here for instant access to the Digital Magazine

Advertisement

From Our Partners

Watch It

Editors' Picks

From Our Partners



Sign up for our daily newsletter and other special offers.
    Choose your newsletters
Thank you for signing up! Your request may take up to one week to be processed.
    see all newsletters