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14th February 2020

People never change. Only situations do. A wise person accounts for this and always bets on human nature over human nurture. Because if you don't, it could possibly end up costing you your life. This is a lesson that I learned on the streets of Chicago and also in the penitentiary. Another lesson that I've learned while doing time is that if you plan to take somebody out, move with surprise, speed, and overwhelming violence...and make sure that you don't miss. This was a lesson that two brothers named Pete and Frank Gussenberg learned the hard way from a man named "Machine Gun" Jack McGurn. The date was February 14, 1929. The place was N.Clark street in the city of Chicago. This was the day that the Gusenberg brothers lost their lives in Chicago's most infamous hit. The St. Valentine's Day Massacre.

The old adage that "Crime doesn't pay" is simply not true. Sometimes it pays very well. If it didn't, you wouldn't have crime and criminals, and you certainly wouldn't have organized crime. But just like almost everything else in life, the difference between a successful criminal and an unsuccessful one, sometimes comes down to timing.

In 1929, the rackets in Chicago were primarily controlled by two criminal gangs. The largest one was Al Capone's Outfit that was based out of Cicero and Chicago Heights. It controlled all of the booze, brothels, and gambling houses on the Southside of the city. The other organization was headed by a wily gangster named Bugs Moran, and his group was called the Northsiders. Their turf encompassed the part of the city that they drew their name from, the North side. They were into all of the rackets that Capone's Outfit was, with the exception of prostitution, which they considered to be seedy and beneath them. But in spite of the the fact that the criminal pie was large enough for both gangs to get more than a slice, Al Capone and Bugs Moran were constantly at war and trying to kill each other.

"Machine Gun" Jack McGurn signed on with Capone in the early Twenties and initially earned about $150.00 a week being one of his gun monkeys. His real name was Vincent Gebaldi and he was Neapolitan like Capone was, but like many Italian immigrants back then, he Americanized his name in attempt to overcome prejudice and blend into society. McGurn became friends with Capone and eventually worked his way up to his inner circle, even playing golf with Capone once a week at a country club in the Chicago suburb of Burnham. If you're wondering why I'm talking so much about Jack McGurn, it's because not only was he the architect of the St. Valentine's Day massacre, he was the cause of it. This is how it went down.

In the fall of 1928, McGurn was in a hotel on Rush street in downtown Chicago. In the lobby of the hotel was a phone booth, and McGurn was inside of it placing a call. Unbeknownst to him, it had been planned that that was to be the last phone call that he ever made. But some people are harder to kill than others, and somehow, against all odds, they manage to cheat death. Machine Gun Jack McGurn was one of these people.

They came for him on a chilly, overcast day. The wind was blowing in off of Lake Michigan and people wore wool coats to try and fight off the chill. This included long overcoats that were capable of hiding a Thompson submachine gun that had a donut-shaped clip attached to it that held 100 full metal jacketed .45 caliber slugs. This particular weapon was the gun of choice for two Jewish brothers named Pete and Frank Gusenberg. These two were the hit team that had been dispatched by Bugs Moran to kill McGurn that day. However, McGurn turned as he was making his call and saw them coming. Unfortunately, there was absolutely nothing that he could do about it though.

In broad daylight with a lobby full of people, the Gusenberg brothers stood shoulder to shoulder, whipped their coats open, and came up with their Thompsons and lit Jack McGurn up. The hot lead sliced through his muscle and tissues like a knife going through a stick of warm butter, and the slugs slammed him back against the inside of the phone booth. There is no logical (or medical) explanation for why he didn't die that day. Because if everything had gone how Bugs Moran and the Gusenberg brothers had planned, McGurn would be dead and there never would have been a St. Valentine's Day massacre. But that's not how things shook out.

Just like a rock dropped onto the still waters of a pond where the ripples ride out to touch distant shores, karma makes its way out into the world, with the ripples eventually making their way back to the person who dropped the rock. In this particular instance, the ripples of the event that happened in the hotel on Rush street made their way back to the Gusenberg brothers some 90 days later.

As McGurn convalesced from his gunshot wounds, he schemed and plotted his revenge. He asked for and received permission to take out Bugs Moran once and for all. Capone gave him an initial $10,000 for expenses and told McGurn to keep him in the loop. Capone wanted to make sure that he had plausible deniability, and that part of the plan worked out just fine. Capone was safe and sound behind the walls of his estate in Florida when the hit finally went down.

McGurn's plan was simple in theory but it had several different parts, all of which were contingent on getting Moran and his men to be in the same place at the same time. To achieve this goal he appealed to the one thing that all of them had in common...their greed. McGurn knew that what he was planning was audacious, even by Chicago standards. So he brought in some out of town talent for the hit. The list of shooters for the job included some of the best killers in the underworld at the time.
-Fred "Killer" Burke from the Egan's Rats gang in St. Louis. Burke was a bank robber and was wanted in at least four states. McGurn considered his participation to be so vital to the job that he paid him $5,000.
-James Ray, also associated with Egan's Rats in St. Louis.
-Joseph Lorlodo
-Albert Anselmi and John Scalise. These were two long-term Capone hit men that had been part of the team that rubbed out the leader of the Northsiders (at the time) Dion O'Banion. A year after the St. Valentine's Day massacre, Capone threw a banquet in their (and Joseph Guinta's) honor at a roadhouse in Hammond, Indiana. He invited 100 guests, and at the end of the evening, he unexpectedly had the three men restrained to their chairs. He produced a baseball bat and announced, "This is what we do to traitors," and then beat them to death in front of the other dinner guests. Their transgression? Plotting against Capone.
-McGurn also brought in two members of the Purple Gang from Detroit to act as lookouts. They were installed in a 2nd floor apartment at 2119 N. Clark street, right across from the headquarters of the Northsiders and where McGurn planned to clip Bugs Moran and his men.

The plan was fairly simple. Through a middle-man, McGurn had sold Moran a truck of Old Log Cabin Canadian whiskey. Moran had whacked it up with the members of his crew, and everything had gone smooth with that first sale. It was during Prohibition, but to make the whiskey extra attractive, McGurn had sold it for $57.00 a case. Afterwards, McGurn laid-back and waited a couple of weeks. Then he offered Moran another truckload of the same whiskey for the same price.

The location of where Moran and his gang was to take delivery of the whiskey was in a large garage behind his headquarters, S.M.C. Cartage Company at 2122 N. Clark street. Moran's bootlegging operation was extensive and this garage was where several of his trucks were serviced. The date and time for the second load of whiskey was set for 10:30 am February 14, 1929. Valentine's Day.

It was cold outside that morning. The wind was whipping in off of Lake Michigan, threading through the buildings and racing through the streets of downtown. The temperature that morning was 18 degrees. Subsequently, Moran and his men were dressed in long coats and fedoras. Their pockets contained several thousand dollars in cash to pay for the whiskey. This group Northside gangsters consisted of:
-A safecracker named John May.
-A saloon keeper named Albert Weinshank.
-Moran's brother in law, Albert Kashellek (who was also a bank robber).
-A racketeer named Adam Heyer. Heyer had brought his dog along that morning. It was a Malinois named Highball.
-Dr. Reinhart Schwimmer, an optometrist who wore a red carnation in the lapel of his suit jacket for Valentine's Day. Dr. Schwimmer was only 29 but he had a store where he "Fitted" and sold eyeglasses and he was quite prosperous. Some say that he was part of Moran's gang, but the prevailing theory is that he liked the fast life and liked to hang out with gangsters. It's said that he was good at his chosen vocation, but apparently not a good enough optometrist to see his death coming that morning.
-Pete and Frank Gusenberg.

These were the seven souls who were in the right place at the wrong time and ended up being immortalized because of it.

Some plans are considered brilliant, while others are simple. But, in the end, a plan is only as smart as the individuals that are tasked to pull it off. To put it bluntly, the two members of the Purple Gang that McGurn had brought in from Detroit and posted across the street from the Northsiders headquarters to act as sentries, screwed up. Their primary function in the hit was to watch the front of the S.M.C. Cartage Company and notify McGurn when Bugs Moran showed up. They'd been given a picture of him to study so that they'd be able to recognize him on sight. Unfortunately for them and for Albert Weinshank, Weinshank looked a lot like Bugs Moran and when they saw him walk into the cartage company they mistakenly identified him as Moran and made the call to McGurn to tell him that he'd shown up.

A Chicago Police Department (CPD) squad car and two patrolman's uniforms had been procured for the hit. Shortly after McGurn received the phone call, the police car sped up to the front door of S.M.C. Cartage Company and its four occupants rushed into the building. Fred Burke and another man were dressed as CPD officers, complete with badges and guns. Albert Anselmi and John Scalise wore fedoras and long trench coats that concealed their Thompson submachine guns. Later on, witnesses would say that they saw two uniformed officers and two plain-clothes detectives jump out of the car and run into the building.

What the witnesses (and the hitmen) didn't see though was Bugs Moran and his two associates Willie Marks and Ted Newberry as they rounded the corner and came walking up the street with their hands dug into their pockets. Upon seeing what they believed to be four legitimate cops go into their building, they turned around and walked away thereby saving their lives.

Upon entering the cartage company the hit team quickly made its way back to the garage. They caught the seven men unaware and they lined them up against the back wall. I would imagine that in the last moments of their lives, they realized that there was no whiskey, and that the men who had their guns trained on them were not real cops. In their wildest dreams they probably never imagined being lined up against a wall and executed though. But that's' exactly what happened next.

Standing side-by-side, Anselmi and Scalise came out with their Thompsons. The other two hit men had a shotgun and a .45 caliber pistol. They didn't ask for money. This wasn't a robbery. The only thing that they were there to steal that morning was lives. Without saying another word, they opened fire. The hot lead made the men against the wall jerk and dance as blood and bits of their skulls splattered against the wall. Twenty seconds and over 100 shots later, the men lay crumpled in a pile on the floor with blood slowly pooling outward from their bodies. Six of them were dead. Or as they say in Chicago, "Graveyard dead".

The four hit men rushed back out the front of the building, and according to their plan, Anselmi and Scalise walked out first with their hands in the air as the other two held guns to their backs to make it look like they were being arrested. They climbed back into the car and sped away into the crisp winter morning...and into the annals of gangster lore.

Highball had witnessed the slaughter of his master as well as the other men, and he was in a frantic state of despair. Still tied to a pipe in the back of the garage, he let loose with long, plaintive, wails until, finally, a woman across the street from the garage went to find out what was wrong. The smell of gunpowder still wafted through the air as she discovered the carnage. She stumbled through the bodies, leaving footprints in the blood, and she untied Highball from the pipe. He took off running and wasn't found until days later. He was eventually adopted by a neighborhood family.

Miraculously, after being shot 22 times, Frank Gusenberg was still alive when the police arrived. They rushed him to the hospital, but when the police asked him who'd shot him, he refused to tell them. His response was that of a true gangster, "What gun shots? I don't know nothing." He died about 30 minutes after arriving at the hospital, taking with him the names of the shooters for what is undoubtedly the most infamous gangland hit in the city of Chicago. Dead men tell no tales. Neither do live dogs.

Although Capone was more than a thousand miles away on February 14, 1929, he still received the blame. It was the beginning of the end for him. Three months later in May, he was summoned to the first National Commission meeting of the heads of all of the Italian-based crime families in the United States. One of the topics on the agenda was Chicago and a way they could reel-in Capone.

He also gave impetus to a 78 yr old man named Frank Loesch who most people have never even heard of. Loesch was the head of the Chicago Crime Commission at the time and the creator of the "Public Enemies" list that J. Edgar Hoover would eventually copy with the FBI's 10 Most Wanted list...

...Something that I would know about all too well in my bank robbing days.

Happy Valentine's Day everyone, and I hope it's filled with much love.

Jeffrey P. Frye
Bank Robber's Blog