Saint Valentine's Day Massacre

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The love story behind the Saint Valentine's Day Massacre.
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Part 2 of the 2 part series

Updated 09/22/2022
Created 01/31/2010
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Saint Valentine's Day Massacre
The love story behind the Saint Valentine's Day Massacre.

Always suspected that it was Al Capone behind the Saint Valentine's Day Massacre, it was never proven and, although he admitted to it in private to his boys, he never confessed the crime to the police.

On Valentine's Day, February 14, 1929, seven men were shot in the back, gunned down, and murdered. Four of the men were with the Bugs Moran gang. The fifth man, was not a criminal, per se, he was the Moran gang bookkeeper. The sixth man was just a gang groupie, an optician, who enjoyed pretending he was somebody tough by hanging around with known criminals. The last man, the seventh man, was an innocent auto mechanic intent on turning his life around.

They were all lined up against a wall and machine gunned to death. How awful? I can't imagine how they must have felt.

Yet, that's all most of us know about this story. We didn't know very much about the victims, except for the assumption that they were all criminals. They weren't. At least one man was a good guy, a family man, trying to turn his life around.

This story is about the auto mechanic. John May was his name. There's not much known about the man. I used what I found on him and imagined the rest. You can call it a creative biography. Only, how awful is it to have lived on this earth and not be remembered? We are all here for just a short time and it's tragic to just be forgotten.

You could say that John May was the auto mechanic for the Moran gang, but that would sound as if he was a gang member, too, and part of their gang, but he wasn't. He just worked in their garage as an auto mechanic, is all. He just serviced their cars. It was just a much needed job to him. This was 1929 don't forget, the time of the worst depression in the history of the United States. He took whatever he could get and John was thankful for the job.

After being arrested twice for blowing up safes and cleared of all charges, John gave up his criminal life and decided to go clean. Some guys can do the time for the crime and when Johnny came close to going to prison, he knew that he couldn't and turned his life around. Getting off scot free was his wakeup call and he retired from blowing safes right then and there. He was done with being on the wrong side of the law.

There was an Angel in his corner that day. He was lucky. Even though they had been using fingerprints since 1915, the database of samples were small and, before computers, fingerprint identification was done by hand and with a keen eye using a magnifying glass, a time consuming process. Without DNA identification, this safecracker was lucky to be able to avoid prosecution, but he had.

Even though he was intent on turning his life around, even though he wanted to stop his criminal ways and go clean, it wasn't easy for him to find a legit job. Everyone was scrabbling for work. It was 1929, the year of the stock market crash, and if that wasn't enough, it was more difficult for him to find a job with his criminal record, something he obviously had, having been arrested several times. It was as if the cards were stacked against him, before his hand was even dealt.

Before fast food joints on every corner, before Home Depots and Lowes hardware chain stores crisscrossed the country, before big rigs traveled superhighways, before superhighways even existed, before Wal-Mart, and even before minimum wage, unless you were a farmer or a ranch hand, jobs were few and far between. It was easier for John May to continue his criminal ways than it was for him to find a job. Nonetheless, John was determined to turn his life around.

His job as a safecracker was high in demand. Back then, most places didn't have alarms. Some places of business didn't even have electricity, yet. What was easy money before, blowing up safes to steal the loot, was a dangerous business now. The police were on to him. They knew who he was and if he made a mistake, they'd nab him. So, he decided to lay low and go straight.

No matter, whenever there was a blown safe and there were quite a few around in this desperate time, hoping to find him with the loot, they picked him up, roughed him up, and questioned him first. Now, so that they didn't pin the crime on him and frame him, he always had to make sure he had an iron clad alibi, otherwise he'd serve time for something he didn't do. The best he could hope for was to keep his nose clean and walk the straight and narrow.

"The safe was blown at the jewelry store downtown and it has your name written all over it, Johnny boy," said the police Lieutenant giving him a hard stare and a punch in the jaw. "What do you know about it? C'mon, c'mon, come clean and we'll go easy on you."

"I don't do that anymore. I'm clean," he said reeling from the blow.

"How do we know you're not lying, Johnny?"

"I'm not lying. I'm telling the truth. There's no use in lying to you coppers. You'd find me out anyway, which is why I'm telling you the truth. I didn't blow up any safe. I'm through with all that. See? I have a wife and kids to go home to. I don't need that kind of trouble no more."

"Yeah, sure, you're innocent. Just like those other safes you didn't blow up. Right? If I didn't believe you then, why should I believe you now? Huh," he said giving him a shove that nearly knocked him off his chair.

"I was cleared of those charges in a court of law. I'm a free man," he said looking up at the cops. "You guys treat me as if I'm public enemy number one. I'm not. I'm just a regular Joe. You're just looking for someone to pin this on, so you can go home to your little lives and fat wives."

The Lieutenant socked him in the nose for that insult, but it was worth it saying that to him.

"Where were you last night? And if you lie to me," said the Lieutenant pointing an index finger in his face, "I'll break out the rubber hose and beat you within an inch of your miserable life."

"I was home with my wife and seven kids having supper. I have eight eye witnesses to testify that I was there. I have a good life now with a good job and a good woman by my side. I'm an honest man." He looked the Lieutenant in the eye. "You have the wrong man. I didn't to it."

"Good job? You have a good job? That's hardly a good job, being part of the Bugs Moran gang. You're still running with your old friend, I see."

"I don't run with nobody. I just work for the man. He pays me to fix his cars. That's all. I keep my nose clean and to the grindstone and my mouth and eyes shut. What they do is their business and not mine. I mind my own P's and Q's. I work my shift in his garage and go home," he said looking up at the Lieutenant expecting him to sock him again for him to rat out his friend.

"What goes on in that garage, Johnny? C'mon, you can tell me. It's just between me and you. No one will ever know you're a rat. What do they do in there, just hang around or is that where they plan their next job? Tell me, Johnny, you could be a hero to your community and fellow man," said the Lieutenant taking out a Camel cigarette and lighting up and blowing a cloud of smoke in his face before offering John a smoke.

"If you're looking at me to be a rat, you've got the wrong guy," said John waving off the cigarette. He didn't want anything from the cop. He just wanted to go home. "I ain't no rat."

"What is their next job? I could use an inside man like you to help me get promoted to Captain and there could be a little extra dough for you on the side. You scratch my back and I'll scratch your back, that's how it works around here," he said pocketing his cigarettes.

"I mind my own business and what they do in their garage is their business. I work on the other side of the garage, far away from them. Except for when they laugh over something funny, I can't even hear them talking. I mind my own P's and Q's, I tell you. My nose is clean. I'm not involved in any of that criminal activity no more. I have a family. I have kids that depend on me to bring home the bacon."

"With all those hungry mouths to feed, you mean to tell me you wouldn't be tempted to grab some easy cash on the side and blow a safe?"

"I'd have to be a dope to try and pull the wool over your eyes, Lieutenant," said John with a snide sneer. "Times are tough, yeah, sure, but times are different, too. They have fingerprints now that would match me to the crime."

"You could always wear gloves, Johnny boy. You could always wear gloves."

"I didn't. See," he said raising up his hands to the Lieutenant's face. "My hands are clean of this job. I didn't do it."

"Get him outta here," said the Lieutenant.

John left the police station glad that he was finally out of that dirty business. He felt better standing up for himself and to the Lieutenant. He wished he could find another job, a better job, and leave the old neighborhood behind, but jobs were hard to come by. He was lucky to have a job at all, as most men weren't working and stood in the soup and bread lines hoping for a handout.

He'd move away from there, but where would he go? Everywhere was the same. The economy was bad everywhere. Besides, moving cost money and he lived week to week.

He had no extra dough, except for what he had squirreled away from the robberies he did and got away with doing, but that money was still hot. He couldn't touch it. He had that safely stashed away, until later, where no one would ever find it.

He didn't even own a car. Cars cost dough, something he didn't have, at least money he could put his hands on and flash around without calling attention to himself. He could just hear that Lieutenant now, if he went out and paid cash for a car.

"Bugs sure must be paying you well to fix his cars. Where'd you get the money to buy that coupe out front? C'mon, come clean. We know you blew that safe downtown."

Imagine a man who fixes cars not even owning one. Yet, that's how it was back then. Not everyone owned a car. These were hard times.

John was always mechanically inclined. Even though he didn't own a car, he could fix them. He could fix anything, even open a safe that was locked without even having the combination.

Bugs Moran was his childhood friend. From working with him blowing up safes, Bugs trusted John May to keep his mouth shut, which is why he helped him to go clean by giving him a job fixing his cars. He knew he could trust him and depend on him.

He understood that Johnny didn't have the stomach for blowing safes anymore. He understood that Johnny was tired of running from the law and trying to stay a step ahead of being arrested, and that was okay with him, and why he didn't ask him to do that anymore. Besides, Johnny had seven kids that needed a daddy and he knew that Johnny didn't want to take the chance that he'd be shot to death, one day, and dumped from a car in an alley leaving his wife a widow and his kids orphans. His family meant more to him than some fast money that he'd just blow through.

It was a woman that changed John's life. It was a woman who he fell in love with. When he promised her his heart, he promised her he'd go straight. He was committed to keeping both his promises to her.

It was different back then. Before Internet dating and cell phones, unless you had a job in downtown Chicago, your ability to find your perfect match was limited to your immediate neighborhood, most times. Most people didn't even have the means or the transportation to stray very far from home. Besides, many of the women back then were cloistered and not free in the way that they are now to explore and experiment with relationships and with sex. Many of the women back then were virgins and if you weren't married before your 21st birthday, you were considered an old maid.

John met Hattie years ago, when he was just a kid. She used to babysit him. Eight years older than he was, he had a crush on her. As he grew to be a man, Hattie was always on his mind and he had a special place in his heart for her. Only, she had moved from the neighborhood to a house across town.

He couldn't put his finger on it, but there was just something about her that he loved. Normally not shy around women, he liked her because she was shy around men. Then, fate stepped in, and after not seeing one another for ten years, they met again one day when he was 19-years-old and she was 27-years-old.

"Hattie? Is that you?"

"Johnny! I can't believe it. You're not little Johnny anymore. You're a man."

Hattie had just broken up with her fiancé and she was ripe for his advances. She didn't want to be an old maid and now she was at the age where most men were beginning to think that there was something wrong with her for her to still be single and without a man. The thing she had in her favor was that she didn't look her age. Genetically blessed, she looked much younger than she was.

"This calls for a celebration," he said. "Let me buy you lunch at the diner."

"I already had lunch, but I'll go with you for a cup of Joe," she said taking his arm.

John bought her a cup of coffee and a slice of hot apple pie at the diner. A sight for sore eyes, after not having seen her in years, she was a looker and he couldn't take his eyes off of her. He was happy to see her. Immediately, he thought of her as a romantic connection, whereas, she thought of him as the boy she babysat, no doubt, and someone from her childhood.

She was 5'2" and shapely and had blonde hair and blue eyes, the opposite of how he looked tall and thin with his dark hair and brown eyes. But boy did she have a body, at least, what he could see of it. He could only imagine the rest and he did. He knew right for the start that she was the one and the thought that fate played such a role in them meeting again, well, it was magic and magical. One never shy around women, he ceased the opportunity of seeing her again by asking her out right there on the spot.

"There's a new Charlie Chaplin movie playing at the cinema. Wanna go? My treat. I can pick you up Saturday."

At first she protested starting a relationship with him because of the differences in their ages.

"I used to babysit you, Johnny. How would that look? I knew your mother. Back then, you were little Johnny. If I went out with you, I'd feel as if I was robbing the cradle. I'd feel funny. I'd feel desperate. I'd feel foolish."

Yet, when he looked in her eyes, Johnny knew there was something real there and he wasn't taking no for an answer. He already let her slip through his fingers once, but not again.

"Ah, that's nonsense, Toots," he said taking a puff of his cigarette and squashing the rest of it in the ashtray. "Our age shouldn't play any part in how I feel about you and I've always thought of you as being swell, just swell. Now that we're older, adults, actually. I'd sure like to get to know you better, Hattie. I'd sure like to show you a good time, Saturday."

"Thank you, Johnny," she said. "You make a woman blush. No one has ever sweet talked me before."

"Well, get used to it, Hattie, because if you were my dame, I'd treat you right. You'll see. I'm going to be somebody." He looked at her, took her hand in his, and smiled. "So what do you say?"

"Okay," she said.

They were good together and everyone who saw them knew they loved one another. They married in 1914. A good Catholic girl, she was pregnant nearly every year for the next seven years.

Maybe because he was so much younger than she was, but the sex they had was incredible. Sex every morning and sex every night, it's a wonder they only had the seven children. She was the only women he was ever intimate with and she was a virgin when she married.

Not wanting her to know that all those kids worried him. A man without so much as a high school education, he had to find a way to support his wife and kids. Only, it was hard times. People were looking for work and couldn't find any. A time not long after the first world war, the economy never rebounded in the way that the politicians promised it would.

His friend Bugs, in charge of the Polish/Irish mob, was making a pile of dough doing small jobs, robbing and stealing with a little bookmaking, gambling, extortion for protection, and some prostitution on the on the side. The Italian mob, the Mafia, allowed Bugs to work, so long as he didn't step on their toes and infringe on their territory. Bugs knew Johnny from the old Lincoln Park neighborhood of Chicago's north side and he know that John was handy with his hands. Knowing that Johnny was having a hard time feeding his kids, Bugs made him an offer that started Johnny down the wrong path blowing up safes.

"It'll be like taking candy from a candy store," said Bugs plying him with drinks.

John, not the brightest crayon in the crayon box, a simple country boy from the farm, his mom lost the farm when his Dad died in a farming accident and sold the farm when John was just a boy. Then, his mother died when he was 18-years-old. Now, alone in the big city and on the wrong side of the tracks, he was trying to make his way in a cold world.

"Gees, I don't know, Bugs. I never did anything like that before. Afraid I'd go to Hell, I never stole anything in my life."

"Don't think of it as stealing, then. Just think of it as borrowing. You'll pay it all back, once you get a good job and get back on your feet. You can make a anonymous donation to the poor box. That's what I do from time to time," said Bugs. "Me and the Father down at the church are on good terms and so long as I'm on good terms with the Father, I'm on good terms with the Lord. Whatever he needs for the poor and whenever he needs it, I take care of it for him."

Bugs made the lifestyle sound glamorous and it was in the beginning. The neighborhood was there's for the taking.

"Yeah, I guess it would be okay, so long as I was gonna pay it all back," he said taking a sip of his whiskey.

"I'm tellin' ya, Johnny, once these shopkeepers go home for the night, there's no one minding the store. The best time to hit them is the weekend. They won't know they've been robbed until Monday morning and by then, we'll be long gone, long gone, Johnny. So, what do you say? Are you in with me?"

What started out good in the beginning turned sour in the end and Johnny wanted no part of it anymore. It was easy pickings helping his friend, Bugs Moran, to blow safes in the beginning. Only, Capone's gang wanted some of the action and was weaseling in on Bugs' territory.

A tough and violent time during prohibition, Al Capone was looking for new ways to fatten his empire. Branching out into other cities and neighborhoods was a ripe opportunity to make some easy dough by pushing out the small time hoodlums and taking what he believed belonged to him, all of Chicago. Capone wasn't afraid to take what he thought was his by force and by paying off the cops, prosecuting attorneys, and judges to look the other way and, if that didn't work, he wasn't afraid to kill people.

With the rash of recent deaths by machine gun, Johnny saw the writing on the wall. He wanted no part of that, he wanted out. He didn't want to die, especially not like that, shot in the back. Unlike some of these other hoods who had nothing and no one, with Hattie and seven hungry mouths to feed, he had too much to live for. He didn't want to die.

Now, with a wife and seven kids later, Johnny was happy that he had escaped jail and was finally free from the life of crime. Yeah, sure, he was making less money working as an auto mechanic, but he had some dough stashed aside for a rainy day that Hattie didn't know about. He wanted to surprise her with a house, one day, when the time was right. Moreover, he could put his head on the pillow without having a handgun beneath it and sleep at night without expecting the cops to break down his door.

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