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Some Theories on the Valentine Massacre
Many theories on the massacre have been put fourth by many historians through the years. All are quite legitimate if you can twist the angle just right, as no one was ever convicted of this heinous crime. Some theories are just preposterous. It was a crime that was heard the world over. Here are some views on what may have happened on that fateful day of February 14,1929.

Intergang warfare, potshots,  mixed with a traitor and control of the booze trade were all of the reasons behind the massacre. This map details the many speakeasies that were found throughout Chicago in the 1920's.

On February 14, 1929 at 10:15 am Chicago time, George "Bugs" Moran's gang has assembled at 2122 North Clark street garage. It is their gang headquarters and also serves as a booze peddling depot.
The front of the Moran warehouse headquarters

A telephone call is made from a rooming house across the garage, as a signal to the killers to prepare their offense on the Moran gang. Albert "Gorilla" Weinshank is mistaken for Moran who has not yet arrived due to a nasty cold.
10:30 a.m., a dark touring police type car stops in front of 2122 North Clark Street. A second fake Police vehicle has already stationed itself in the alley along with a truck. The truck enters the garage
and the occupants of the police car also enter before the garage doors close. Once inside the fake police let in the killers stationed in the front of 2122 North Clark Street.

The police type touring car stop in front of 2122 North Clark street.

Two carloads of fake cops(Killers) entering the back and letting the others through the front door.
View of the back today and in 1929.
(Photo Bill Helmer / Mario Gomes)

Moran's gang members and associates are lined up against the wall.

The Moran boys are puzzled as they are sure graft is being paid to avoid these hassles from police. They assume that this is all a show for the public, to reassure them that the law is at work. The Moran boys do not worry as they are confident that they will beat the rap as soon as they get a hold of their perspective bail bondsmen.The fake police remove all weapons from the gangsters. John May the garage mechanic who is pulled from under the vehicle he was working on persistently protests his innocence and disclaims being part of the gang.He has promised his wife Hattie he will try his best at keeping straight .John was an ex-safeblower. He carries a St. Christopher medal in his back pocket. Reinhardt Schwimmer a longtime gangster groupie suddenly gets a rush of adrenaline as he is lined up with his longtime heroes. He is a failed optometrist who loves to be in the company of gangsters and loves to boast to anyone who will here that he can have anyone whacked as he so desires. This arrest will make the papers and will  finally show his friends that he wasn't lying about his mobster connections.
The fake police remove the weapons and are startled by a police type alsatian dog chained to one of the vehicles. They breath a sigh of relief as they realize that the dog is tied securely and cannot attain the intruders. Through a crack of the front office partition the signal is given to the other two plainclothes killers waiting in the front office. They begin entering after assembling their Thompson submachine guns.

The signal is given for the rest of the hit team to enter
the garage with their Thompsons.

Top view of killers entering the garage from the office.

 Overhead view of lineup and garage scheme

The killers enter the garage and line themselves up to prepare the slaughter  of the Moran gang. This can be retribution for the following reasons;

1)  The Gusenbergs attempts on Machine gun Jack McGurn's life.

2) The killing of Al Capone's choice for the Unione Siciliana Tony Lombardo and Pasqualino LoLordo. These two men were killed by the Moran mob in a union with Guiseppe "Joey" Aiello who also coveted the title of head at the Unione and promised to appease the Moran mob if they would help him get rid of Capone. Alone, both these mobs would have problems, but united it made this more feasible.

3) The constant stealing of Capone Old Log Cabin Bourbon whiskey sent to him via the Detroit Purple Gang. The whiskey is brought in from Montreal, Canada where it is manufactured by Distillers Corporation Ltd. Moran was said to have had a deal with Capone in buying this whiskey. After wanting bigger profits he decided to sell cheaper stuff and broke away from the Capone deal. Now his sales dwindling, he asks in again with Capone who refuses. Moran decides to steal it from Capone. (This deal is only speculation).
Moran was said to hate Capone with ultimate zeal and visa versa which makes any patnership highly unlikely.

4) Cleaners and Dyers association which was part of the clothing industry. This and other type unions forming had promise for a lot of money making schemes.Weinshank was Moran's man on the Northside for this venture. Capone began his assault and wanted to expand also in this and restaurants, tailors, cleaners, maintenance food supply etc...
The killers from all evidence used two Thompsons one with a 50 round drum and one with a 20 round stick.
This theory is put out by Rick Mattix and Bill Helmer, who I think are right on the money, as the newpapers of that time exaggerated the amount of bullets found on the scene, especially with the amount of time the killers were inside. Sensationalism was the order of the day amongst newspapers. While still a gory scene, it certainly wasn't comparable to a world war battlefront as one witness had stated at the time. Not many bullets missed their targets and as many as 70 spent shells were found leaving to believe that the stick mag was used alongside the drum in case the drum mag jammed. (Which happened on occaision as it did on the Weiss hit).  

The killers let go with Thompsons

The killers sweep back and forth, up and down upon the Moran gangsters

Highball the Alsatian dog is tied to a truck and cannot free himself to attack. A .38 said to have been hidden by the Gusenberg's is projected across the room and is found a few feet away from the entrance.

Top view of massacre scheme.

Once their mission completed the plainclothes killers exit and the fake police follow simulating a fake arrest.The getaway driver is waiting in the car while the massacre took place.

All members of the Moran gang are wiped out instantly except for Frank Gusenberg, (far left) who manages to live for another 3 hours. His bedside interrogation reveals nothing.
He is found crawling towards the door when the real police arrive.
On the chair is Peter (Frank's brother), next on the floor from left to right with hat on his chest is Albert Weinshank, Adam Heyer (lessee of garage) ,
John May(Mechanic) and Reinhart Schwimmer(gangster groupie who got more than he bargained for that day). Alongside wall is James Clark (Albert Kachellak).

After the hit, the killers make their getaway.
A woman next door sees the men leaving and is still perturbed by the gunshots she has heard minutes before while ironing clothes. She sends a roomer in the building to go in and investigate. He wearily opens the front door which by the way, was quite stubborn to open as the winter cold had swelled the door making it stick. Once inside the roomer could smell the acrid smoke of gunpowder. As he enters the partition, he sees figures lined up on the floor and hears a dog whimpering. He has seen enough and runs out exclaiming "There are full of dead men in there"
The police are summoned and an investigation begins. Crowds are gathering in front and back of 2122 North Clark street to get a peek at all those dead men.

 Crowds begin to gather as police investigates.

another view of crowd.

The killers to be as follows;

Fred "Killer Burke
Fred Goetz"Shotgun" Zeigler
Robert "Carey" Conroy
Ray "Crane Neck" Nugent

In the car waiting was Gus Winkeler, although his role and Ziegler's can very well have been reversed.
The sure one as look out across the street must have been Byron "Monty" Bolton  because of a medicine bottle and a letter both with his name on them were found shortly after massacre. He was later confessing in taking part, but was discounted by a certain J Edgar Hoover. The massacre remained a police matter and the F.B.I kept clippings about it, but that was as far as they were willing to go.   

Fred Burke wearing police clothes and sunglasses was identified through ballistics as having posession of the Thompson fired at he massacre. He's smarter than he looks, as he had killed a police man in another state to avoid being prosecuted for the massacre, and avoided getting whacked. Some witnesses said they saw a policeman with a missing tooth. Fred Burke had one front tooth missing. He was also the type that if he had to kill a 100 men for pay, he would do it no questions asked.

Fred Goetz Shotgun Zeigler
I think would have no problem killing everybody in that garage.
He was a promising edcuated man gone beserk first raping a young child and committing robberies and murder. Was whacked in Cicero with a 1,000 bill in his pocket.Hung with the likes of the Barker-Karpis gang.

"Big Mike" Gus Winkeler also from the same school as Burke.
Another who wouldn't think twice to get the job done. His particiaption in the hit probably got him to control the Northside till Capone went away and Frank Nitti started to get paranoid of being overthrown. Nitti despised the "American boys" as these elite killers and guns for hire were known by the underworld. Nitti started to have anybody who showed power whacked one by one. Gus got whacked!  

As we well know this is just might of happened as any scenario can be made to fit and look good. Some although must be discounted. For me while Tony Accardo was later a man tailored for mob boss, I do not think he took part in the actual massacre as some authors suggest. He was still an up and comer and probably took part in getting rid of evidence such as clothes and cars along with Tough Tony Capezio who himself almost blew up blow torching a car to pieces. He forgot to remove the gas reserve canister before torchcutting the car.

But why kill these gangsters if the main target George Moran wasn't there? Itching to get the plan executed for nearly two weeks, the lookouts probably had mistaken Weinshank or Schwimmer as Moran arriving at the garage. The real Bugs Moran saw the police car in front of the Clark street garage and high tailed it to a coffee shop. The killers upon arrival asked no questions and wiped out the Moran associates.
 The dog tied to the vehicle was so frightened by the gunfire, that he had to be put down. Newspaper photographer John "Hack" Miller said that he adopted the dog, but this was later discounted by Chicago sun photographer Russell V. Hamm, who said that the dog was too wild after this event. Russell also states that he was one of the first on the scene and was handed cameras from other photographers to take photos from atop a truck full of cypress wood This because the police were telling them to hurry up.

Al Capone certainly knew about this hit and condoned it. He might have planned it much better as the result brought about his ultimate downfall. Jack McGurn certainly took part in the planning. When he was picked up days later at his Stevens hotel apt., the detectives found newspapers for several days opened on pages containing the Massacre. He claimed he was in bed with Louise Rolfe for the whole day on Feb. 14. I read alot of info, obtained many clippings from fellow historian Larry Raeder, and see that a lot of the investigation seemed to have strong leads and just be sidetracked.

A Capone / Circus cafe gangster named Tony Capezio is torch cutting a vehicle used in massacre when an explosion ensues hurting him. Nothing comes of this by police. Investigating is presumed Capone paid Detective Daniel "Tubbo" Gilbert. Not far from garage and massacre scene is the Circus Cafe. This is a hangout for the Capone sattelite gang. The Cafe is owned by Claude "Screwy Moore" Maddox. Hangersout at the Cafe include McGurn, Capezio, Accardo. Police investigating massacre make a raid at the Circus cafe finding a drum from a Thompson and find several rounds matching the brand in the Massacre. Again nothing comes of this. Claude Maddox is brought in, but released. McGurn with his  blonde alibi is also released from 7 charges of murder for the massacre.
J. Edgar Hoover and the FBI recieve several letters from crackpots who claim they know who did it. Most of them wild and wooly. The FBI file them nontheless in their archives and will not bother to investigate because the Massacre was strictly a Chicago Police matter and not a Federal one.

John Scalise one of Capone's killer twins is charged with 7 counts of murder in the massacre. He gets off by getting killed in Capone's baseball banquet after it is learned that he and Anselmi along with Joe "Hoptoad" Giunta are planning to kill Al and take over. Their bodies are found in a car along a ditch in Hammond Indiana. Newspapers immediately jump om the Moran revenge for the massacre theory. That is quickly dismissed. A car is also found in Maywood believed to be part of massacre. The touring car contains a notepad / address book belonging to Albert Weinshank, who is killed in massacre. Nothing comes of this! Fred Burke is visited by Capone man Phil D'Andrea while in Marquette prison.
Herman Bundesen is also threatened many times to let go on the investigation or else! With Chicago being such a corrupt place in the twenties, I feel the investigation was purposely sidetracked and eventually halted.

Byran "Byron" Bolton one of the lookouts later confesses and gives authorities details which point to the St. Louis crew of Burke and company of which Bryon was riding with at the time of the massacre. A letter addressed to Bolton along with a medicine bottle bearing his name is found in one of the lookout rooms across the street of the massacre building. The FBI not wanting to look like numbsulls by some two bit criminal immediately discredit Bolton's admission.    
Bolton will die in the 70's while living in California. It still remains unsloved and will probably remain that way forever as the years go by.         


First Posted May 2001