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Tuesday, September 1, 2020

The Characters Behind the Characters - The Gentleman Thieves

The Characters Behind the Characters - The Gentleman Thieves   

C. A. Asbrey

It’s no secret that The Innocents Mysteries Series is partially inspired by the story, and the movie, Butch Cassidy and the Sundance Kid. The idea of popular outlaws, who planned and trained to be better at stealing, and who had a mystique which followed them into a charismatic twilight of a mythical new life which allowed at least one of them to life happily-ever-after in domestic obscurity is an enticing trope. It seemed even more exciting to make the love interest a woman on the other side of the law.
But it also took me on another line of research. My characters were criminals, but who had limits as to their cruelty and venality. But did people like that really exist, or was it just a romantic fiction? Without dwelling too much on the story of Robert LeRoy Parker and Harry Longabough, and whether or not either of them did manage to go straight and live happily ever after, what about the rest of the criminal world?
My Innocents Mysteries series of books feature criminals who, while not being exactly squeaky-clean, are polite(ish), humane, and even chivalrous. So, did people like that actually exist or is the concept ridiculous?  

Charles Arthur Floyd

Let’s start with those who were definitely out for themselves, but who didn’t mind helping out the little fella while he was there. Charles Arthur Floyd, A.K.A. Pretty Boy Floyd hated his nickname.  A payroll master at a robbery described Floyd as “a mere boy — a pretty boy with apple cheeks.” Like his contemporary Baby Face Nelson, Floyd despised his nickname. His dying words, after being shot multiple times were in response to being asked if he was Pretty Boy Floyd replied, “I’m Charles Arthur Floyd.” Despite  an active criminal career he was often protected by locals in Oklahoma, where he was seen as the “Robin Hood of the Cookson Hills”. He had a reputation of helping to look after the grindingly poor by raiding shops to give away the food to starving people. He was also said to destroy mortgage records when he raided banks, although how the householder was supposed to know the bank no longer had proof of their mortgage debt is not clear.
Due to the violence of the men he worked with it’s hard to put Charles Arthur Floyd in the category of Gentleman Thief, but he does nod towards the dichotomy under discussion.

James Freney

Our next Gentleman thief actually lived to a relatively old age (69) for the 18th century and certainly seems to be a better fit for the model. James Freney was an Irish highwayman in the 18th century. He was driven to a life of crime when the bar he ran made insufficient profits to pay the exorbitant fees charged by the city corporation. He was officially proclaimed an outlaw in 1748. At the time, Ireland was suffering under England’s Penal Laws, which kept the Irish out of many  professions. This repression drove Freney to close down his pub and saddled him with so many taxes that he had little choice but to look outside the law to make ends meet. He lived to his otto, “Rob only those who are worth robbing.”
Like every true gentleman criminal, Freney insisted his gangs adhere to a code of honor, which included remaining courteous, returning goods if they held sentimental value or the victim needed them, and assisting the poor whenever possible. Even so, he was a first-class marksman and never feared getting into a brawl if someone crossed him.
He reigned supreme in his area for five years before he was captured. Freney work out a deal with the chief justices in which Freney would be allowed to emigrate as they feared civil unrest of such a hero was hanged. His gang were not so lucky and ended their lives on the gallows.  He published his autobiography, The Life and Adventures of Mr James Freney in 1754It was a huge success and Thackeray included Freney in the novel The Luck of Barry Lyndon, where he has Barry encounter Freney on the highway. The incident appears also in the film Barry Lyndon (in the film, Barry refers to the man about to rob him as “Feeney”). Local landmarks named after him include Freney’s Rock and Freney’s Well, and he was the hero of The Ballad of the Bold Captain.

Bill Carlisle

Our next candidate  for Gentleman Thief was one of the last great train robbers of the American Old West, a career he took up on something of a whim. An orphan, he drifted from one job to another, riding trains, working in the circus, and performing other odd jobs. In February 1916, he found himself in Wyoming with no prospects, only a nickel to his name, and a gun. Carlisle’s first holdup was a dime novel stereotype. He sneaked onto the train and fired a warning shot into the roof to prove it was a legitimate robbery (there were some doubters). He covered his face with a white bandana, gathered the loot, but tossed a few coins to the porter to make up for lost tips. He gave another man a silver dollar to pay for his breakfast. A woman tried to grab his gun, but he evaded her and gave her a bow before leaping from the train. The “White Masked Bandit” was now $52 richer. and he didn’t stop there.. He robbed Union Pacific Railroad several more times until they eventually offered a $6,500 reward for his capture, dead or alive. That’s $150,030.73 today. Motivated by the large reward money, a posse caught him in May 1916, and Carlisle was sentenced to life in prison. He later escaped, was recaptured, and then was paroled in 1936 for good behavior.Like other gentleman thieves, Carlisle had a moral code. As he never hurt anyone and never stole from women, children, or servicemen, I think he is a good candidate for the title. In one of his capers, he was attempting to rob a train when he realized it was full of soldiers returning from World War I. He let the men keep their money and claimed that he would have fought alongside them had he not been in prison at the time.

Bill Miner

Bill Miner epitomized what it meant to be an Old West outlaw and he had a longer career than Jesse James. This was mostly because he was terrible a evading capture and spent most of his career in jail. He was imprisoned seven times, escaped four of those times, yet still spent a total of 35 years behind bars. His criminal career stretched between 1865 and 1911. He was a true highwayman, robbing everything from stagecoaches to trains, and he spent his money on women and whiskey – and as the old saying goes, wasted the rest. He was reputed to be the first to say “put your hands up, and nobody gets hurt.”  Unlike other outlaws, he wasn’t known for spittin’ or cussin’ or gun-slinging. He was polite and soft-spoken. After his death, a major newspaper ran a four-column story on Miner, describing him as a “kindly, lovable old man, whose thoughts were humorous, whose manner was that of one who was a friend to all humankind . . . the most courtly, the most kindly spoken, the most venerable man . . . one whom they all regard with affection and something of esteem.” Miner had secured that soft spot in so many people’s hearts by stealing almost entirely from corporations, feeling that they robbed the common man. Many agreed, and he became a folk hero in both the US and Canada. On the occasions when Miner had to steal from an ordinary person to, say, facilitate his way out of town, he often made a point to return at least part of what he had taken. For instance, on one occasion, he stole $80 from a ranch hand and then later returned $10. In another instance, he robbed a driver of $5, his watch, and boots, yet was considerate enough to return the watch and boots after he finished with them. These types of thoughtful acts earned him the nickname “the Gentleman Bandit.”

Charles Earl Boles  (Black Bart)

 Black Bart was one of the first Gentlemen Thieves I came across and I admit to a sneaking affection for him, and for the fact that he later disappeared and nobody knows what happened to him. After the Civil War, Charles Boles was a former First Sergeant in the Union Army, and was happily making a living as a gold miner when he was forced off his land by Wells Fargo. They had apparently offered to buy Boles’s property they cut off the water supply when he refused. This shut down his mine. Boles was infuriated and cryptically wrote a letter to his wife saying he was going to take revenge against the bank. While he never explained the specifics of his vengeance, we can assume this is when his alter ego, Black Bart, was born.
From then, Black Bart had it out for the bank and subsequently robbed their stagecoaches 28 times. He was civil, never physically harmed anyone, and stole strictly from Wells Fargo and never from passengers. Even the bank described him as being non-vicious and “polite to all passengers, especially to ladies.” Amazingly, he traveled on foot to and from robberies and carried a shotgun so old that it couldn’t shoot (he didn’t even bother loading it). Although he always worked alone, he would often prop up sticks on nearby boulders to make it look like he had a posse of men standing by.Occasionally, he was thoughtful enough to leave poems behind—Wells Fargo was not amused. His last poem read: Here I lay me down to sleep
To await the coming morrow
Perhaps success, perhaps defeat
And everlasting sorrow
Let come what will, I’ll try it on
My condition can’t be worse
And if there’s money in that box
‘Tis munny in my purse.
Black Bart’s unique style and sophistication made him a hero in California (except to Wells Fargo), and it took over a decade before he was finally tracked down by Pinkerton Detectives. He went to San Quentin Prison for four years and was released early, in 1888, for good behavior. He disappeared shortly after and was never seen again. I like to think he went off quietly somewhere with a stash of cash to enjoy a happy retirement.


“She hasn’t got the combination to the safe,” said the manager. “You can scare her as much as you want. We all know you’re not gonna use that gun on us.”

Rebecca’s breath halted as she felt a careless arm drape around her shoulder.

“I don’t need a gun to hurt someone. Give us the combination.” The manager remained mute and turned his face away. “Your call, sir.” He pulled Rebecca around to face him as she gasped in alarm. “Just remember who you’ve got to thank for this, ma’am.”

He pointed over at the manager, who refused to meet her eyes. “That man right there.”

“Anything that happens to her is down to you. Not me,” said the manager.

Rebecca felt herself dragged from the room by one arm. She was pulled into the office next door and pushed against the wall. The man walked over and pulled down the blind before returning to her. Her breath came in ragged pants of fear. “Please, no. Don’t.”

He leaned on the wall, a hand on either side of her head, and pressed his face close. “You were gonna hold this place up. Are you some kind of idiot?”

She blinked in confusion. “Huh?”

The man pulled down his mask, revealing the face of the fair man who had walked into her office looking for Fernsby. “Don’t lie to me, honey. You had the same idea as we did— look at Meagher’s bank account to see where he gets his money. We’ve watched you march up and down outside this place all day, like you were on sentry duty, while you built up your courage. You even got in the way of us doin’ it. What the hell is goin’ on in your head? How dumb can a woman get?”

“You? Here?” She couldn’t quite decide whether to stop being scared or not.

“Yeah. Me.” He indicated with his head. “Now, Nat’s in there, and he needs the combination of the safe. It’s too new and sophisticated for him to crack the combination. You and me need to put on a bit of a show to make sure the manager gives it up.”

“You’re not robbing the bank?”

Jake huffed in irritation. “Try to keep up, Becky. I need you to scream for help so the manager gives Nat the combination to the vault. We want Meagher’s records too.”

She shook her head. “Me? I can’t scream.”

“What do you mean you can’t scream? All women can scream.”

“I can’t. I’m just not made that way.”

He frowned. “Look, Becky. If you won’t scream, I’m gonna have to make you. Let’s do this the easy way, huh?”

“Please, help! Noooo.”

Jake frowned. “You call that screamin’? That’s useless.”

“I told you. I can’t.”

Jake flicked up an eyebrow. “Last chance, Becky.”


“Nope.” A gloved hand reached up to her hat as his eyes glittered with mischief. “Don’t say you weren’t warned, sweetheart.” 




  1. I had to sympathize with some of the outlaws because they were either given a raw deal hat led to their crimes or they did good deeds that seemed to make up for the laws they broke.
    It's a funny thing about western law; so many lawmen were once criminals depending on the town they happen to be in.
    You wrote a very interesting perspective on these "gentleman" outlaws in your blog Christine.
    All the best to you...

    1. Thank you, Sarah. I think the chaos of the Civil War, poverty, lack of opportunity, and desperation led many people into a life of crime when they would have stayed honest in another life. As you say, many changed sides, some disappeared into what we assume was an honest obscurity, and many died far too young. Tough times, tough people, and tough choices.

  2. Why someone enters into a life of 'crime' is a constant source of speculation. Some you can understand, but others?

    I truly enjoyed your list of gentlement bandits and agree with your list. Great role models for this fun series. Doris

    1. Yes, there are many reasons for entering a life of crime. Understanding those certainly helps us build realistic characters. Thanks for commenting, Doris.

  3. I really enjoyed reading about the backgrounds of these men, some of whom I'd never heard of. It's always interesting to learn why someone turns to criminal behavior, and fascinating to think about why someone chooses that path while many others in similar circumstances don't.

    1. It is. Some do it for easy money, some through chaotic childhoods, desperate poverty, some because it's all they know. As a cynical ex-cop, I think that for many it depends on how likely they think they are to get caught. All grist to the mill for characterisations. Thanks for commenting, Ann.

  4. Love this blog, Christine. Years ago I came across an article about Gentleman Jim and wanted to write a story about an outlaw like him, but never did. It's always interesting to learn what made a good man choose to walk...or ride on the wild side. And I love your excerpt. Crime stories are always more fun when they're infused with some humor.

    1. Thank you so much. We ll love a bad boy, but we don't want him to be TOO bad, do we?

  5. Sorry that the first week of classes kept me from reading and commenting on this sooner. Interesting stuff -- and intriguing to think about the different behaviors of different lawmakers. I especially love Bill Miner returning the boots and watch. And I remember Black Bart used to call himself a "poe8" which seems very modern, somehow.

    1. He did? That does seem like text speak. I hope the term settles for you soon. You'll be back in the swing of it before you know it.