A Bootlegger’s Generosity

December 25th 1930

Samuel Chilton lay beside his wife as the sound of children echoed throughout the tenement building.  One of these days, one of those shrieking high voices would be his and perhaps he wouldn’t mind it at all. The faint sound of the Millers’ radio permeated the bedroom with the irresistible strings of George and Ira Gershwin’s “Embraceable You.” He was almost tempted to shout out to Hal Miller to raise the volume up slightly so that it might wake Sandra up and perhaps they could have a quick dance.  Instead he lay there watching her sleep resisting the temptation to stroke her fine black hair that adorned her pillow almost artistically. Any minute she’d wake up and he’d have to bid her farewell although not for as long as the average day.  She’d no doubt protest about the fact that it was Christmas Day, but a kind look from him would let her know that they should both be grateful he found work otherwise Christmas Day would have been spent just as Thanksgiving Day was spent standing in line at the corner of 9th and State Street for most of the entire day.

Sandra’s eyes began to flitter as she stretched and began wiping the cobwebs from her eyes.  Her ears, perked up by the sound of the music, slightly twitched as a tired yawn transformed itself into a smile as she realized Sam was watching her.  Her perfectly rounded face composed itself as her mouth pursed itself into a shape that Sam always found loveable.

She reached out for him, but he took her hand and regrettably told her, “You know I have to go.”

“But it’s Christmas Day, Sam. Can’t they give you a break from unloading those infernal trucks at least today?”

“I’m new, darling.  If anyone’s got a day off it ain’t gonna be me.”

“I hate that you’re doing this, you know.  It’s bad enough you’re engaged in something I’m morally opposed to, but today of all days.”

“Sandra, it puts food on the table, and Mr. Capone’s a good man for giving me this job.”

“Listen to how you obsequiously refer to him as if he’s some kind of savior.”

“They may have instilled this self-righteous attitude into you at Hull House, but let’s face it. Jane Addams isn’t feeding you now- I am.” Sam paused a minute knowing that he regretted his tone.  His face changed and grew more benevolent as he apologized for his outburst, “Listen, I’m sorry. I know it’s Christmas.  I’ll be back as soon as I can. Besides, it’s not like we have any kids.  We’re grown adults who could get through the day without resorting to some fanciful notion of the Holiday. Are we not?”

Sandra sighed, “I suppose I have no choice but to agree,” she relented and brandished a tearful smile, “Dress warmly, Sam . . . I love you.”

“I love you too,” said Sam, “Remember you married a barber not a philosopher.”

“It’s too bad Mr. Conners had to let you go last year.”

“One day I’ll have a barber shop of my own and no one could lay me off no matter how badly things get with the economy, but until then we must do what we must.”

“Potato Soup and chuck roast for dinner?”

“Sure, we can afford it now. I figure by February we might even have enough to leave this place.”

“But you’ll still be working for . . .,”Sandra stopped herself, “Never mind. I don’t wish to upset you again.”

Sam left with the loving image of Sandra in her plain white nightgown and her bare feet standing by the lime green Windsor stove.  He’d have to give her the book he bought her later on when he returned, and as he exited the building he closed his eyes and imagined the smile that would cross Sandra’s face when he gave it to her.   It was Margery Allingham’s novel, Mystery Mile, and for months it was all Sandra could talk about.  It wasn’t stocked at the Hardin Square Library, “If the author was a man they would have it,” Sandra would say.  Somehow one of her friends from her days at Hull House had read it and told her about it only that friend had just borrowed the book from someone else and wasn’t in the position to loan it to Sandra at the time.  That’s when Sam knew he had to find it.  Sandra loved to read, and he imagined one day the two of them would have a house with a library of its own comprising of far more books than might be possible to read in one lifetime.  Some day in the distant future, this copy of Mystery Mile would be displayed prominently as a reminder of just how far the two of them had come.

As he walked passed the Soup kitchen on 9th and State Street, he saw a line that seemed to go for miles.  If it wasn’t for Mr.Capone, he’d be on that line.  Hell, if it wasn’t for Mr. Capone these people on this very line would have nothing to eat today.  He remembered how just last month for the very first time, he and Sandra were forced by necessity to spend Thanksgiving at Al Capone’s soup kitchen, where men, women, and children could get a free hot meal all funded by the generosity of Mr. Capone, who Sam believed cared about this city more than the mayor, the governor, and both senators combined.  The newspapers reported that Mr. Capone fed over 5,000 people that day, and Sam and Sandra were among them although the free meal did nothing to quell Sandra’s contempt for the man.  Sandra supported Prohibition, and while neither one of them were heavy drinkers before the law passed a decade ago when they were both still very young, Sandra had thought she’d see a real positive change in the city.  After all, with women just beginning to vote, things were bound to get better.  Neither one of them could foresee the circumstances that would lead to Sam getting laid off from Conner’s Barber Shop and endless months of being amongst the unemployed.

Things changed last month on Thanksgiving though.  While waiting on line, Sam could hear the sound of Capone’s armored Cadillac pulling up alongside.  Capone exited the vehicle with all the bravado he had been depicted with in the papers.  The crowd cheered and shouted, “Thank you, Al!”  and “God bless you, Al!” as he posed for the newspaper cameramen eager to get a decent photo for their featured stories. Capone acted every bit the hero, spouting instructions and proclamations as he walked along the line shaking hands, “I want to make sure everyone here gets a decent hot meal!  This is my way to give back.” He lit his cigar and boisterously chuckled to himself as he glad-handed as many men and women who were eager to see him, “I, too, came from meager beginnings but I worked hard and now look at me.”

Sandra wasn’t as impressed with him as Sam was.  Sam had already been acquainted with Al as he occasionally cut Al’s hair back when Al would come in to Mr. Conner’s barber shop.  The man always tipped well, and no matter how he made his fortune, Sam believed that what Mr. Capone did to give back to the community made up for all of it.  As Mr. Capone drew closer, Sam stuck his hand out and a few second later a firm grip grabbed his hand and he found himself in front of Mr. Capone with all the nerves of a school girl.

“Didn’t you used to cut my hair at Conner’s barber shop?” asked Mr. Capone.

“Yes sir.  That was me. My name is Sam Chilton.

“What are you doing here?”

“Well, Mr. Capone, Mr. Conner had to lay me off a while back so my wife and I have fallen on hard times.”

“Sam, I’m so sorry to hear that.  You know what, come to my warehouse tmrw over on Hubbard Street.  You want a job, Sam?”

“Nothing would please me more, Mr. Capone.”

“Well, enjoy your meal today and then see my brother at the warehouse tomorrow 9am sharp. I’ll let him know you’re coming.”

“Thank you, Mr. Capone.  You have no idea how much this will mean to us.”

Sandra stood behind expressionless trying her best to avoid eye contact with Capone, but just before Capone turned, he put his arm around Sam and drew himself near Sam’s ear, “Tell your wife she should learn to like me more, uh. She probably didn’t hear that I’m giving you a job.”

Sam could hardly contain his enthusiasm, but ever since that fateful Thanksgiving Day this new job had been a constant source of friction between him and Sandra.  Walking by the soup kitchen, he observed all the wretched lowly lives clamoring for their free meal and told himself how grateful he was not to be in that line today.

Over by the warehouse on Hubbard Sam could tell Mr. Capone’s brother, Ralph Capone, was in a disgruntled mood. The ruggedly stocky man barked his orders at the men as they moved expeditiously along the line of trucks, “Come on guys!  It’s Christmas. Let’s move it.  The sooner we get this over with the sooner we’ll all be done and we could all go back to our families.  You think I want to be here with the lot of you?  Let’s go!”

Sam got to work loading his assigned truck.  Most likely he’d have about 3 or 4 speakeasies to deliver to before calling it a day, which wasn’t so bad. Plus there was talk of Christmas bonus for the men if they finished early.  He’d prepared himself to be home in plenty of time for Sandra’s delicious supper.  In the month since he started he had been treated very well, and Ralph even complimented him a few times.  Working for the Capone Outfit felt very much like working a regular factory job. His father had worked at a button factory, and for the life him, Sam felt as if his current employment opportunity was very similar.  It was mindless labor instead of the care and precision that went into being a barber.  There was hardly any artistry that went into loading crates on a truck and unloading them at their eventual destination.  All the talk in the newspapers about Capone’s Outfit wreaking havoc on the city seemed like a load of hogwash.  There had been the supposed, St. Valentine’s Day Massacre a year ago, but Capone wasn’t even in Chicago when it happened.  Here was a man, Sam thought, who had only benefitted his community.  What good was Prohibition anyway?  It was nothing but the government attempting to deny the public alcohol out of some delusional notion that making it illegal would get people to stop drinking.  Mr. Capone was simply giving the people what they wanted and what harm was it to anyone anyway if you wanted a drink?   The speakeasies brought people together to dance, laugh, and socialize.  Yes, occasionally there might be fights and obscene drunken behavior, but no number of laws was going to stop a drunk from drinking anyway.  To Sam, Mr. Capone was merely a smart business man, and after making his fortune Mr. Capone could have withdrawn himself to a mansion and never bothered with Soup Kitchens and giving jobs to people like him, but instead Mr. Capone gave back to his community.  Isn’t that what America is supposed to be about?

Sandra vehemently disagreed with him. She had gone to Women’s Temperance League meetings back when the woman’s suffrage movement was fighting for the right for women to vote.   She argued that so many men ruined their families due to their drinking.  Eliminate the drink, and those same men could be productive instead of squandering their wages on alcohol. She thought America should be about building up families, and all alcohol did was encourage men to be lascivious drunken whoremongers who would no doubt mistreat their wives and families.  When the law passed, she was thrilled that there would be a real change, but then the papers began to flourish of talk of organized crime and violence sweeping the city.  The criminal element took control of the distribution of alcohol rendering Prohibition nothing but a superfluous law that only existed on paper.

Sam thought to himself about Sandra as he loaded the truck. He couldn’t wait to give her the book he had bought for her, and perhaps one day she may slowly change her mind about this job of his.  As he hummed “Embraceable You” to himself he could hear screeching tires approach the ware house.  6 men exited the long black vehicle with Tommy Guns and began to open fire, “IT’S THE MORAN GANG!” yelled someone from a distance. Sam tried to take cover but as he was in between the crates and the trucks he couldn’t decide whether he should dive towards the crates or in the other direction towards the trucks.  His mind raced to make a decision but his body stood frozen.  He couldn’t bring himself to move.  As he dropped the crate from his hand, Sam finally decided to move towards the trucks and attempt to dive between them to try to take cover.  He could see himself sliding across the floor, his breath escaping him with the sweat from his brow streaking across the floor behind him.  He could almost feel himself getting to relative safety, but realizing his body had not made any such move yet he tried to get his legs in front of him and after having made perhaps half a step towards the truck, Sam’s lifeless body dropped to the ground after a fatal shot to the head. People yelled and screamed for him to move but he would never hear them.  Sam, for all he was worth, lay flat motionless on the warehouse floor as Moran’s men escaped in their vehicle.

Minutes later, Ralph Capone called his brother,”Snork, you better get down here.”

Al Capone strolled into the warehouse office where he found his brother, “What the hell happened?”

“Moran’s men – that’s what happened,” said Ralph.

“So, who’s the guy who bought it?”

“New guy sent here last month – Chilton.”

“I remember that guy.  He had a wife, no kids though.”

“You want me to send someone over to her, Snork.”

“No, Ralph.  I want to do this.  It’ll mean more coming from me.”

Ralph told his brother about the book they found in Chilton’s pocket, “Seeing as how it’s a female author we figure it must have been for his wife.”

“Give it to me then.  I’ll make sure she gets it.”

Sandra had prepared her meal for Sam when she heard a knock on the door.  She found it unusual since Sam would have just let himself in.  She thought maybe it was a neighbor asking for milk or butter or some other such thing.  When she opened the door to find Al Capone standing in her doorway, her face became white with shock and confusion.

“Mrs. Chilton?” asked Capone.

“Yes, what is it you could possibly want here?” said Sandra.

“So, you know who I am,” said Capone.

“Yes, I know who you are.  Where’s my husband.”

“I’m afraid there’s been an accident.”

“An accident?” Sandra’s face distorted itself with incredulity

“You see there was a shooting at the warehouse and sadly your husband, Sam, is no longer with us.”

Sandra couldn’t bring the tears that her body was summoning to her face because the rage swallowed them down in her stomach.  She couldn’t believe what she was hearing.  She began to slump over, but just as Capone tried to catch her she violently repelled herself from him.  “Get away from me you monster!”

“I know you’re upset, but that’s why I’m here.  As the man in charge I want to try to help you.  Here …” Capone took out an immensely bulking money clip and almost simultaneously took Sandra’s hand to put the money into it.

Sandra clenched her fist pushing Capone’s hand away, “I don’t want your money.”

“There’s 5 grand in there – enough to get by for a long while ‘til you get back on your feet.  Take it.”

“Is that what you think fixes everything?”

Capone shook his head, “No, it doesn’t fix anything but it’s the least I can do.”

Sandra shook her head saying, “Get out.”

Capone searched for the right words to say but then remembered that he had the book. “Look, I have this.” Capone took out the book and showed it to Sandra.  Perplexed, she reached out for it questioningly, “I think he was going to give this to you today.  We found it in his jacket pocket.  Really, Mrs. Chilton, you should take the money or I’ll just leave it.  I don’t even consider it mine anymore.”

Sandra composed herself, “I’ll take the book and only the book.”

She snatched the book from Capone’s hands and fixed her eyes on the red dust jacket endearingly. Capone turned around, and as he was about to leave the money by the shelf near the door, Sandra stopped him, “Don’t you dare leave that money!”

Capone turned around, confused,” Mrs. Chilton, I’m trying to do something generous for you.  Will you please be reasonable and let me do this.”

Sandra’s face quickly grew stern, “No.”

“And why not?  You got any family, mam?”

“Both my parents died when I was young, and I had 2 brothers die in the war.”

“I’m sorry to hear that, mam.  You know the war . . . that’s how I got these scars. Faced off against the kaiser himself. . .”

“Somehow I doubt that,” said Sandra with as much contempt as she could muster. “You talk of generosity but fail to know the meaning of the word.  I’m an educated woman. I don’t need to be given charity from the likes of you. “

“Mam, I don’t want to argue with you. You’re obviously very upset. I feed thousands of people every day out of my own pocket.  Thanksgiving Day, that day I saw you and your husband on line, Well that day I fed over 5,000 people who otherwise would have went without food.  That’s gotta count for something.  I know you maybe don’t like me, but I’m a good man with a family . . .”

Sandra interrupted, “A man with a family who controls nearly every whorehouse and speakeasy in town. You open a free Soup Kitchen and feed the poor and you think that makes up for the scourge you and your kind have brought to this city since you ensconced yourself here?  Well, it doesn’t.  This city has suffered because of you and now I’m going to suffer because my husband got himself killed working for you.”

“Take the money, mam.  It’ll beat the soup kitchen.”

“I’d rather wait on a thousand breadlines than accept that money from you. You think you own this town?  You think you’re a hero? One day your name will be recalled in infamy and jest, and no one will ever remember the soup kitchens or the big tips or your picture in the paper.  You’re a hypocrite and a fraud and one day everyone will realize it and no one will fear you like they do today.”

Capone stood silent for a moment.  Then, he turned around, took the money, replaced it in his pocket and left.  Sandra collapsed onto her hard floor.  The tears she failed to summon upon first hearing the news of Sam’s death now came flowing out of her.  The beautifully round face that Sam had admired that very morning now flattened collapsed by the weight of anguish and tears.   She would grieve for Sam harder than she grieved for the death of her parents, and yet just as she was about to let herself sink further she found the book Sam had bought for her staring back at her.  There was a quiet strength she could sense emanating from it as if it came from Sam.  She could now feel him quietly caressing her frazzled black hair almost whispering, “It’ll be alright, my love.”  Sandra got herself back up with the book clutched in her hand breathing deeply.   She closed her eyes and imagined Sam softly telling her, “You could do this.”

As midnight approached on Christmas Day, 1930 Sandra Chilton may have been alone, but she was confident she’d never need a hand out or a soup kitchen ever again.

Author’s Note: I tried as best I could to get this story to feel as authentic as possible, but I did write it rather quickly trying to incorporate as many facts as I could without bogging down the story itself.  If anyone has any suggestions or has any comments please feel free to comment below as I view this story as more of a work-in-progress draft rather than a properly finished story.  I’m sure there will probably be errors I’ve overlooked as well as things people may disagree about concerning the period and whether or not Capone would go through the trouble of talking to a widow of a man who was killed working for him.  I hope anyone who reads it enjoys it anyway despite my limitations – Jack Lugo


    1. Thank you so much for reading my story. I’m very glad you enjoyed it. The authentcity is what I was most concerned with so I’m glad you found it to ring true to the time. Sometimes it’s intimidating to set stories in a setting that you can only read about so thank you for the encouragement.

      Liked by 1 person


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