The alpha male bandit and the beta male baker

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Leroy Leonard – don’t be this guy! Wait a minute…Leroy who?

I’m pretty sure that nobody reading this has ever heard of Leroy Leonard, but more than likely you have heard of the man who cuckolded him. So let’s begin with a brief bio of Charles Arthur “Pretty Boy” Floyd.

Floyd was born in Adairsville, Georgia on February 3, 1904, and moved with his family to eastern Oklahoma when he was a boy. His upbringing was fairly typical of rural youths at that time. His family was hardly affluent but no one missed any meals. It could be described as hardscrabble light. For the Floyd family, as with many others in those days, producing moonshine was commonplace. Of course, if you want to make corn liquor, having a cornfield on your property gives you a head start.

Floyd progressed from making moonshine and petty larceny (his first brush with the law was literally penny ante: stealing a jar of pennies) to grand larceny, mostly bank robbing, which entailed occasional casualties and a number of confrontations with lawmen.

As was the case with many an outlaw in those days, Floyd’s exploits were as much legend as fact. He was accused of far more crimes than he could have committed, and much like Jesse James, he was something of a hero to the locals.

Eastern Oklahoma was still relatively wild and wooly in Floyd’s days (the 46th state in the union, Oklahoma did not achieve statehood till 1907). In its territorial days, it was something of a sanctuary for all sorts of bad hombres. Most of the gallows fodder put before Judge Isaac Parker (a/k/a the Hanging Judge, who served on the bench in Fort Smith, Arkansas from 1875 to 1896), was harvested from the IT (Indian Territory) by federal marshals. (The old Clint Eastwood movie, Hang ‘Em High, is a pretty decent re-creation of the times). Pretty Boy Floyd’s old stomping grounds were just a few miles west of Fort Smith.

Pretty Boy’s legend was spread by many unfortunate people (the Great Depression started early in rural America) to whom he had given a helping hand. Most country folk admired Floyd and few were inclined to help the minions of the law. Doubtless many people experienced vicarious enjoyment from his exploits and admired his pluck. He life of crime was, in a sense, a success story. If crime is “a left-handed form of human endeavor” (according to the crooked lawyer in The Asphalt Jungle), then Pretty Boy Floyd was a left-handed version of Horatio Alger.

Before he became a serious criminal, Floyd made the acquaintance of one Ruby Hardgraves, a sharecropper’s daughter; he was 19 and she was 17. Sparks flew and continued to fly. The two were inseparable and eventually married (she was pregnant at the time) on June 28, 1924 in Sallisaw, Oklahoma.

Soon after his son Dempsey (named after heavyweight champ Jack Dempsey) was born, Floyd got into armed robbery. After unwisely flaunting his ill-gotten gains, he attracted the attention of local authorities, who traced his boodle of cash back to a St. Louis payroll robbery. He was remanded to Missouri for trial, found guilty, and sent to the state pen in Jefferson City, Missouri. He was 25 years old when he was released on March 7, 1929.

Absence had not made Ruby’s heart grow fonder. Rather than stand by her man, she divorced Pretty Boy while he was in stir. Here is where Leroy Leonard enters the picture.

Leroy Leonard wasn’t as sharp as Pretty Boy Floyd, but he was a sharp contrast to him. Leonard was a classic beta male, reliable, hard-working, steady, and probably dull. Yet he was the answer to a single mother’s prayer, and he bonded with Ruby and her son.

Call him a sucker, a simp, a sap, or what you will. Maybe he was just color-blind and didn’t recognize the red flags. They were:

(1) Ruby was divorced;

(2) Ruby was a single mother; and

(3) Ruby’s first husband was a notorious outlaw who was still at large.

Gee, what could go wrong?

At any rate, Leonard married Ruby and took her and her son to the southeast Kansas town of Coffeyville, where he worked in a bakery. That move might have been an omen, since the town was synonymous with bank robberies, more specifically, botched bank robberies. On October 5, 1892, four members of the Dalton gang were killed in the act while attempting to rob two banks simultaneously.

As a bank robber, Floyd was a better provider than Leonard. He was daring and dapper – hence his nickname. Not only was he Pretty Boy, he was the Phantom of the Ozarks, and the Robin Hood of the Cookson Hills. Though Floyd operated mainly in the Midwest, he was as much a national celebrity as any movie star or sports hero, despite the fact that his occupation dictated that he avoid photo ops rather than seek them out.

Maintaining a low profile was no problem for Leroy Leonard. In Pretty Boy: the Life and Times of Charles Arthur Floyd (St. Martin’s Press, 1992), author Michael Wallis describes Leonard as a “twenty-two-year-old hardworking man she [Ruby] had met in Oklahoma. He was very much in love with Ruby, and he was kind to her own little boy. Friends remembered that he treated Dempsey as if he were his own son.”

“Leroy was always very good to me and my mother,” recalled Dempsey many years later. Yes, Leonard was a nice guy, and as Leo Durocher supposedly said, “Nice guys finish last” – or in this place, second. Leonard could not compete with Pretty Boy Floyd, the man or the legend.

Unbeknownst to Leroy, his wife had renewed her acquaintance with her ex-husband. She had not sought him out. One day he simply appeared on her doorstep in Coffeyville and sparks started flying again. Dempsey recalled that his first memory of his father was that day in 1931.

Imagine poor Leroy Leonard walking home after toiling all day in the bakery to find out that his wife’s first husband, a notorious outlaw, is a houseguest. Not only that, his wife and stepson are about to take off with him – that very evening.

How can a time-clock-punching wage slave compete with a celebrity gangster? As a baker, Leroy Leonard might have come home with dough on his hands, but Floyd came home with fistfuls of dough to show for his labors. Ironically, Floyd enjoyed baking as a hobby.

Leroy learned the hard way that distressed damsels, once rescued, aren’t always grateful. At least not as long as they still have sexual market value (Ruby was 26 when she renewed her relationship with Floyd). According to Wallis, “Leonard’s heart was broken by the callous way Ruby treated him after he had been so kind to her and the little boy he loved.”

Floyd was no fool, however. While he could not shake his attraction to Ruby, he realized that she had already divorced him and had walked out on her second husband. So Floyd kept another woman on the side.

Even in absentia, Floyd proved useful for Ruby. During the last year of Floyd’s life when he was in hiding, she and Dempsey took to the vaudeville circuit and lectured on how crime does not pay.

Pretty Boy Floyd had always suspected as much, even as he enjoyed the fruits of his labors. Having vowed never to return to prison, he knew his end would likely be a violent one. And so it was when FBI agents gunned him down in an eastern Ohio cornfield on October 22, 1934. At the time, Floyd was officially Public Enemy No. 1, a status bestowed on him by J. Edgar Hoover after the feds took out John Dillinger in Chicago on July 22. Floyd’s reign at the top of the heap was only three months but he went out on top. He died an alpha male.

Leroy Leonard might have found some satisfaction in Pretty Boy’s demise. Beta males are the unsung heroes of society and their lives are rarely chronicled, so we don’t know too much about Leroy Leonard aside from his tangential relationship to Public Enemy No. 1. No telling how long Leroy Leonard lived, but he lasted longer than Pretty Boy Floyd. As reported in Wallis’s biography, in 1935 Leonard married “a loving woman and they raised a family.” After that, he disappears from the narrative.

As for Ruby, she continued down the trail of broken marriages and ended up a broken woman. She died, appropriately enough, in Broken Arrow, Oklahoma in 1970.

So the fable of the Baker and the Bandit (the occupation listed on the paperwork for Floyd’s funeral) offers life lessons for young men. Pretty Boy Floyd’s brief life proves that crime doesn’t pay.

Neither does rescuing damsels in distress. Leroy Leonard could vouch for that.

Feature image: Charles Arthur “Pretty Boy” Floyd

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