One of Capone’s ally and also a close friend in Brooklyn, New York was Francesco Ioele a.k.a. Frankie Yale. He was one of the most powerful gangsters at the time who was involved in numerous rackets, such as labor racketeering, gambling, dockside extortion and bootlegging. Besides the Purple gang in Detroit, Yale was also a major importer of Canadian whiskey who supplied part of Capone's booze shipments. But in 1927 the long friendship Between Yale and Capone began to fade away. Yale was the main guy who oversaw the shipments of booze that were meant for the Chicago mob so one day many of the trucks began to have problems with hijackings. So Capone suspected a double cross and decided to send James "Filesy" DeAmato to keep an eye on his trucks. DeAmato was one of Al's top advisors and was also he’s spy in case of any internal rebellions. Later DeAmato reported that Yale was hijacking Chicago’s booze. On July 7, 1927 DeAmato was gunned down on a Brooklyn street corner. Things got worst for their relationship the same year when Yale invited Capone and his arch enemy Joe Aiello to New York for a sitdown at the Jack Sharkey vs. Jack Dempsey fight. The problem was the control over the Unione Sicilani organization in Chicago. Capone expected to be backed up by his old friend but that didn’t happened. Yale decided upon a middle course and told both warring factions to make peace and split the profits. A month later Capone invited Yale to Chicago to view the Dempsey-Tunney heavyweight title rematch at Soldier Field on September 22, 1927. While their visit was civil enough, the pair's friendship began to rapidly deteriorate after Yale returned to New York. Distracted by a gang war with his rival mobster Aiello, Capone had to wait for retaliation. So time has come in the spring of 1928 for the plan to kill Frankie Yale. Capone called Jack McGurn for an advice on who should receive the contract on Yale. McGurn said that the boys from the North Side would be the perfect hit team for the job because no one in New York knew their faces. Capone agreed and ordered McGurn to call his boys from the Circus gang and to give them the contract. Later McGurn visited Claude Maddox at the Circus Café and told him to make the logistics on the hit and also gave him cash and few addresses on the whereabouts of Frankie Yale in New York. Because Yale was no easy target, Maddox decided to call his two most skilful associates such as Fred Burke and Willie Heeney. Later Capone also sent for Louis Campagna to join the team so the four hitmen hopped in a dark Buick and drove off to New York.
When they arrived in the Big Apple, they took an apartment in Brooklyn and stalked Yale for almost a month, just to learn his everyday routines. They found out that Yale had a new young wife by the name of Lucy and together they had 1 year old daughter. They also found out that Yale was very sensitive and carrying towards Lucy so the hitmen decided to take an advantage of that. One Sunday afternoon, on July 1, 1928, Yale was playing cards at his Sunrise Club, located at 14th Avenue and 65th Street, when suddenly he received a cryptic phone call. The caller said something was wrong with Lucy and his daughter and that he should come home fast. In a panic moment, Yale took off with his brown colored Lincoln coupe without his bodyguards. Yale drove up to New Utrecht Avenue, where the hitmen in their Buick sedan drove next to him. Yale noticed the hit squad and took off west onto 44th Street, with the Buick close behind him. The chase continued but Yale's car was soon overtaken by the Buick, whose occupants riddled Yale with bullets. Yale lost control of his car and crashed into a stoop of a brownstone at No. 923. He opened the door of his car and fell to ground. One of the hitmen got out of their car and pumped few more bullets into Yale’s body. The job was done. Maddox and his men left the scene and drove nearly three blocks away where they abandoned their car and left on foot. Later the cops found the abandoned Buick and inside they found a .38 caliber revolver, a .45 automatic, a sawed-off pump shotgun, and a Thompson submachine gun. Also the cops managed to trace the submachine gun to a Chicago sporting goods dealer named Peter von Frantzius. Frantzius was Chicago’s most famous legal guns supplier at the time so it was very hard to tell who bought the gun from him. Later the cops repeatedly questioned Capone and some of his gang associates about the Yale murder, but nothing came of the inquiries.
Frankie Yale death scene
By now Cicero area was the main and also most lucrative territory for the Capone gang. Back in the 1924 the infamous Jewish mobster Edward “Eddie” Vogel was the one who invited the Capone gang to Cicero. Vogel needed help for fixing the 1924 mayor elections. Capone knew that if he played along with Vogel and helped in the elections, millions of dollars could be made from this lucrative territory. At the same time the Capone gang was having problems in Chicago with the newly elected and non-corruptable Mayor William E. Dever so it was a smart move for Capone to relocate in Cicero. Cicero became Capone’s wide open territory for operating gambling, booze and prostitution and also became know as “Caponeland". Capone himself was accommodated at The Hawthorne Hotel at 4823 22nd Street and believe it or not, his main protection was the Circus gang. Capone was at the top floor and Willie Heeney was on the floor below him. Heeney was his chief of staff, meaning if anyone wanted to send message or any kind of information or wanted to make a contact with the Big Fella, Heeney was the got-between guy. Next door to Heeney, was Claude Maddox who was armed to the teeth and was also in charge for the security around Capone and the establishment. Every room, window, and door in the place was completely dedicated to the safety of Al Capone, with double locks, latches, and buzzer systems. Young Tony Accardo was always seated in the lobby of the hotel with a Tommy gun in his lap covered with a coat. Capone also had many other luxurious establishments and secret hideouts around Cicero so it was very hard for any rival gang, including the government, to locate him.
Immediately after the murder of Frankie Yale, Joe Aiello decided that he needs another strong alliance so he can win the war against the Capone mob. Aiello realized that the enemy of his enemy is actually his friend, so he sent word down to George “Bugs” Moran and invited him for a sit down. At the meeting Aiello offered Moran a portion of his gambling empire on the North Side in return for muscle and protection. Al Capone heard about this alliance so he also decided to call a meeting and to end this problem once and for all. Capone called a meeting in late October, 1928 in the Chicago Heights area, which was a place he often used as a hide out. Capone gathered his men at the house of the new rising boss of the Chicago Heights faction, Vincenzo Ammirato a.k.a. Jim Emery. Other gangsters who attended this meeting were Frank LaPorte, second in command of Emery, Sam Costello, the boss of the Sicilian faction in the Heights, James Summons, a known murderous Capone hoodlum, Louis Campagna, Rocco DeGrazia, and Circus gang leaders Claude Maddox and Willie Heeney. There were two agendas at this mob convention, one was the placement of Emery as the new boss of the Chicago Heights since his previous boss Dominic Roberto was exiled to Italy, and the second agenda was the Bugs Moran problem and how to solve it. As usual they decided that a hit on Bugs Moran would be the smartest thing to do. There’s no need for any explanation about this idea or solution because most of the men who attended this mob meeting (Capone, Heeney, Summons, Maddox, DeGrazia) were all former and current enforcers and had more muscle than brains.
(standing from the left) Rocco DeGrazia, Louis Campagna, Claude Maddox, Fur Summons, Sam Costello
(sitting on the ground from the left) Frank LaPorte, Vera Emery, Al Capone, Willie Heeney, Jim Emery
Somewhere around late November 1928, Capone called for another meeting with the boys from out of town. The meeting took place at a house on Cranberry Lake, six miles north of Couderay, Wisconsin. Present at the meeting were Frank Nitti, Louis Campagna, Fred Burke, Gus Winkler, Fred Goetz, the First Ward Republican committeeman Daniel Serritella, North Side politician William Pacelli, and Capone himself. Byron Bolton also attended this meeting but he’s role was to serve the big shots with drinks and meals. This organized crime convention lasted for almost two weeks and the men were hunting, fishing while planning the murder. They decided that the boys would be the prefect guys for the job. The job of the crooked politicians was to take care of the law during and after the hit. Since he was Chicago’s most famous mobster and was usually blamed for every crime that occurred in the city, Capone decided that it’s better to leave town during the operation and to enjoy his summer home in Miami, which would also be his alibi. So he left his two main strong-arm men Frank Nitti and Jack McGurn to oversee the operation. Later McGurn handed over the making of the logistics to the chief of the current most deadly squad, Claude Maddox.
In the next few months Maddox, together with his associates Goetz, Heeney and Capezio at the Circus cabaret were making the plan for the most infamous gangland extermination in Chicago’s underworld history. First they had to find and pay someone from the Moran gang so they can receive information about their boss’s future whereabouts. But the thing was that Moran’s associates were very tight with their boss so no one would rat, so Maddox thought of another idea. He knew that the Moran gang supplied their booze from the same place as he did, and that was the Purple gang in Detroit. So Maddox contacted his associates in Detroit and arranged a deal with them to call Bugs Moran and to sell him a load of hijacked Old Log Cabin whiskey below the market price so Moran can leap at the offer with out any second thoughts. Second Maddox had to use his hitmen from out of town because they were unknown to the Moran gang and the public also. Maddox decided to use his usual four hitmen, including Fred Burke, Fred Goetz, Gus Winkeler and Ray Nugent. They would all receive a $5,000 payment for the lob. They also decided to mask two of the hitmen as police officers so the rival gang would think that it’s an ordinary police raid. They also had to use untraceable getaway cars for the hitmen to be carried to the exact destination. In December 1928 they bought a police Cadillac from an auto dealership on Irving Park Road. The Cadillac previously belonged to Cook County Commissioner Frank Wilson. The guy that was sent to buy the car identified himself under a different name such as “James Morton (Martin?) of Los Angeles”, which in reality was Byron Bolton. They also bought another car, Peerless Sedan, under the same false name. Bob Carey would drive the false police car with Burke and Goetz dressed as cops and James Belcastro would be driving the other car with the other two hitmen, Winkler and Nugent, dressed as civilians. Jimmy "The Swede" Moran and Byron Bolton would be the crew to watch over the Moran gang and there will be a second lookout with Tony Accardo. Tony Capezio and Raymond Schulte would be assigned as the cleanup crew to get rid of the evidences, such as the cars that would be used in the hit. And since this was a high profile hit and the cops and also the whole city knew about the conflict between the two gangs, all of the high profile Capone members had to find their own alibis. The stage was set.
On February 1, 1929 some member of the Purple gang called Moran and said that he had the shipment with booze ready and will deliver it on February 14, 1929, Valentine’s Day, between 10 and 11 a.m. Moran assured the caller that he would be there with his crew to help unload the truck in the gang’s garage on 2122 North Clark Street. Than the caller informed Claude Maddox that Moran will be waiting for a shipment of booze on Valentine’s Day at their hangout on N. Clark St. Maddox immediately sent for Byron Bolton, Jimmy Moran and Tony Accardo to rent a room along North Clark Street across the garage.(as additional info some sources say that Jimmy McCryssen was there instead of Accardo, but years later an FBI bug records a conversation that Accardo was one of the guys) So Bolton and Jimmy rented a room at 2119 N. Clark St. which was owned by Mrs. Michelle Doody and Accardo accommodate himself on 2125 N. Clark St. at Mrs. Minnie Arvidson’s apartments. The three men represented themselves as cab drivers who worked the night shift and they insisted on rooms in the front, overlooking Clark Street. The three men rarely left their rooms and for the next ten days they constantly overlooked the area. Their job was to watch for Bugs Moran and to make a phone call to the Circus Café and to inform the hit squad the second when Moran and his gang will enter the garage. In the end Claude Maddox was struck by luck, when he was called on the same day February 14 to appear in court for a previous gun possession. It was the perfect alibi for Maddox. Al Capone also had his perfect alibi to appear in the police station in Miami the same day. Frank Nitti also skipped town and went to St. Louis with his girlfriend and together they got married over there, thus forming a perfect alibi. Jack McGurn arranged a hotel room at the Hotel Stephens to celebrate Valentine’s Day with his blond girlfriend Louise Rolfe.
So Bugs Moran had called the gang the night before and told them to be at the garage early, because he was expecting a shipment. The morning on Thursday February 14, 1929 the temperatures were bellow zero and the streets were covered with snow and ice, thus causing a bad rush hour. The first Moran associate that came to the scene at about 8:30 a.m. was John May. The two Gusenberg brothers, Frank and Pete, arrived at about 9:30 a.m. followed by James Clark, Adam Heyer and Dr. Reinhardt Schwimmer who was only a friend of some of the gang members. The last to enter the garage at 10:30 a.m. was probably Albert Weinshank, the man who very much resembled Bugs Moran. And that’s when Byron Bolton from the lookout crew across the garage made a mistake. He thought that Weinshank was in fact Bugs Moran because from a distance he bore a big resemblance to Moran. And so Bolton made the call to the boys at the Circus Café and informed them that their target has arrived. The killers were waiting in their cars in a rented garage at 1722 North Wood St. The garage was rented under a false name of “Frank Rogers”. With the signal from Bolton they headed for the SMC Cartage Company garage. The killers took north along Wood Street for a mile to Webster Avenue, then east for two miles on Webster to Clark, which would have taken about fifteen minutes. The first car with the fake policemen arrived at 10:45 a.m. in front of the garage and the second car left the two killers in civilian clothes at the back of the establishment. The two “cops” entered the garage and their role was to persuade their victims to surrender their weapons without a fight, which was the reason behind the police uniforms. The “cops” rounded up the seven men up against the wall. Than one of the “cops” opened the back door and let the other two men enter the garage. The two guys pulled out their two Thompson machine guns and the “cops” pulled out a shotgun and a revolver. Suddenly machine gun rifles were heard all around the neighbourhood and each Moran gang member was riddled with bullets. After the murder, the hit squad then staged their final part of the job and that was to confuse any witnesses as they reappeared on the street. The two hitmen who posed as policemen, took out the other two men as their prisoners, entered the fake police car and sped away. Also the lookout crew vanished at the same time. The killers came back and left the fake police car at the rented garage on Wood St. and fled.
The infamous photo of the St. Valentines Day Massacre
When the real cops arrived at the scene they were so shocked of the sight of the dead men that haunted them for the rest of their lives. The scene was so shocking, that the dog that belonged to one of the Moran members and was also the only “witness,” had to be put to sleep. The cops noticed that one of the seven men was near death crawling to the door. Miraculously Frank Gusenberg survived the shooting and lived for 3 hours with 14 slugs in his body. One of the cops that first arrived at the scene was Sgt. Thomas Loftus and questioned Gusenberg. Loftus asked "Do you know me Frank?" Frank replied "Yes, you are Tom Loftus." Loftus then asked 'Who did it or what happened?" Frank replied "I won't talk." The officer then replied "You are in bad shape." Frank said "For God's sake get me to a hospital." Loftus than asked Frank if they were lined up against the wall and again he answered “I won't talk.” Once transferred to Alexian Brothers Hospital, Loftus asked Gusenberg one last question and that was if the killers wore police uniforms because he previously received information that two men in police uniforms walked out from the garage. To this Frank answered "Yes"' and then he died.
Frank Gusenberg
On February 22, the “cleanup crew” consisted by Tony Capezio, Joseph Lolordo and Raymond Schulte needed to get rid of the getaway cars. First they dynamited one of the cars in west suburban Maywood, the area where Claude Maddox and his family lived at the time. Than they came back to the garage at 1723 North Wood St., to demolish the second getaway car (the phoney police black Cadillac) with acetylene torch, axes and hacksaws. But Capezio made a mistake that nearly cost his life. While he was cutting through the gas tank with the acetylene torch, a fire broke out and blew him to the ceiling, knocking him unconscious. The reason was that he forgot to empty the gas tank. Capezio burned his arms and hands, so Schulte took him to the North Avenue clinic, but when they arrived there they suddenly ran back out because they realized that someone might’ve heard the blast and would be calling the cops. This stunt earned Capezio’s nickname “Tough Tony.” Several years later bank robber Alvin Karpis, who was a close friend of Capezio's, confirmed this story. So when the fire broke out in the garage the firemen who answered the call discovered the black Cadillac that had been partially demolished and called the cops. Some of the witnesses said that three men were seen leaving the burning garage after the car exploded and at least one was said to be injured.
The partly demolished car
The problem was that the cops found out that the man who rented the fake police car under the false name “Frank Rogers” also gave his address as 1859 W. North Avenue, which was a place just few doors behind the infamous Circus Café. That’s when the cops suspected that the Circus gang had a hand in this bloody situation. They immediately arrested Claude Maddox who was found in his Circus Café. The cops searched the place and found a Thompson drum full of cartridges and many overcoats strewn about the back of the cafe. They also found a loaded .45 in one of the overcoats. Maddox was brought in the police station for questioning, but he was later released when he showed his alibi by being in court on an unrelated charge at the same time when the massacre occurred. Judge Peter H. Schwaba confirmed Maddox presence in his court from 9:30 to 12:15 o’clock on the same day of the murders, which took at about 10:45 a.m.
Later the police formed another theory, and again Maddox was also implicated. Few weeks before the massacre Capone gang associates Harry Burton, Frank Carlson and James O’Brien were arrested in a house near Crystal Lake for the kidnapping of wealthy automobile dealer Thomas Gaynor. They constantly tortured their victim and demanded $100,000 for his release. Maddox immediately ordered his associates to collect a defence fund to pay the bail. During the trial, Burton was acquitted but the other two guys were sent to 5 years in jail. This action called for an investigation of the jury and one juror was sent to six months in jail for taking a bribe. Two weeks after the release of Burton the massacre of the Moran gang occurred. Investigators later learned that Burton and his associates were suspects in a similar massacre that occurred in Ohio, when three hitmen dressed as policemen entered a garage and killed five embers of a beer gang.
The cops also questioned all of the residents in the neighbourhood and the people who lived around the garage where the massacre occurred. When they questioned Mrs. Michelle Doody, she said that there were two guys in her rented apartment on the second floor, who constantly overlooked the street and rarely got out. The cops felt suspicious and decided to check out the apartment. During the search, they found a letter and a prescription bottle with the name of Byron Bolton. They didn’t thought about the significance of this clue until years later. But either way they started a search for Bolton for any possible explanation. But the thing was that by this time the out of town hit squad and Bolton fled the city and they were hiding out from any possible questionings by the police.
Cops standing in the room where the lookout crew resided
It doesn’t matter whether this bloody massacre was arranged by Capone or not, in the minds of many Chicagoans and citizens around the country, Capone went from being a role model to Public Enemy No. 1. The St. Valentine’s Day Massacre, which appeared in every newspaper front page around the country, was the final blow to Chicago’s already bloody reputation. The Chicago Association of Commerce immediately posted a reward of $50,000 for the arrest and conviction of the killers. And additionally the angry public collected another $10,000 for the reward. The city council and the state’s attorney’s office each added $20,000, bringing the total to $100,000, the biggest price ever put on the heads of gangsters. The Capone mob made few fatal mistakes during the arranging of the massacre and blew their cover. Capone was known for saying that "If you want something done right, then just do it yourself." This was the beginning of the end for the infamous Capone gang and the rise of a new criminal organization that the world has never seen before.
A special crime investigation committee takes an oath before the murder victims in the massacre
On February 26, 1929 Deputy Police Commissioner John Stege issued an order for the arrest of 17 well known criminals in the Chicago area. He believed that some of the men on the arrest list may have been the actual killers and the other might have knowledge about the situation. The first one to be arrested was James Belcastro because his description given by a witness corresponded with the description of a man with a missing finger on his hand that drove the getaway car. Belcastro was a known bomb maker in Chicago and lost one of his fingers during an incident. Second on the list was Jack McGurn but he had a strong “Blond alibi. His girlfriend backup his story and the cops found room service orders from the time when the massacre occurred. Again Claude Maddox found himself at the top of the suspect list and was taken for questioning. Maddox was a major hope for the investigation but he disappointed the cops because he kept his mouth shut and they had nothing on him. The cops also arrested Joseph Lolordo because he lived next door to the garage where the demolished car has been found. Danny Vallo, it was said, had voluntarily appeared at police headquarters when he previously heard about the arrests. During the arrest of Circus gang member Sam LaVerde and his sweetheart, who gave her name at one time as Dorothy Smith and at another as Dorothy Cohn, were taken into custody while riding In LaVerde's automobile. In her bag Dorothy carried a notebook with telephone numbers and addresses from many establishments. While investigating the notebook, the cops found the address of an alleged beer flat. In a matter of hours the place was raided and the cops arrested Fred Emery, a known rum runner from Detroit. He was question whether he was in any form implicated in the massacre but Emery denied any associations with the mentioned suspects. Others arrested were Willie Heeney, Raymond Schulte, Tony Capezio, Rocco Fanelli, Tony Barone, Frank Diamond and also Bugs Moran and some of his friends and allies, including Sam and Joe Aiello, Rocco Griffo, William Rode, Charles Kakel, Frank Milici and George King. The cops also questioned the Jewish mob boss and Capone’s right hand man Jake Guzik. They had records that Guzik called Capone in Florida from The Congress hotel shortly before, and after the massacre went down. No one dared to talk.
