The Saint Valentine's Day Massacre is the name given to the 1929 murder of seven mob associates as part of a prohibition era conflict between two powerful criminal gangs in Chicago: the South Side Italian gang led by Al Capone and the North Side Irish gang led by Bugs Moran. Former members of the Egan's Rats gang were also suspected of having played a significant role in the incident, assisting Capone.
Massacre on St. Valentine's Day
Chicago's gang war reached its bloody climax in the so-called St. Valentine's Day Massacre of 1929. One of Capone's longtime enemies, the Irish gangster George "Bugs" Moran, ran his bootlegging operations out of a garage on the North Side of Chicago. On February 14, seven members of Moran's operation were gunned down while standing lined up, facing the wall of the garage. Some 70 rounds of ammunition were fired. When police officers from Chicago's 36th District arrived, they found one gang member, Frank Gusenberg, barely alive. In the few minutes before he died, they pressed him to reveal what had happened, but Gusenberg wouldn't talk.
Police could find only a few eyewitnesses, but eventually concluded that gunmen dressed as police officers had entered the garage and pretended to be arresting the men. Though Moran and others immediately blamed the massacre on Capone's gang, the famous gangster himself claimed to have been at his home in Florida at the time. No one was ever brought to trial for the murders.
The Downfall of Public Enemy No. 1
Though the St. Valentine's Day Massacre marked the end of any significant gang opposition to Capone's rule in Chicago, it can also be said to have marked the beginning of his downfall. With his highly effective organization, his impressive income and his willingness to ruthlessly eliminate his rivals, Capone had become the country's most notorious gangster, and the newspapers dubbed him "Public Enemy No. 1." Federal authorities began investigating Capone after he failed to appear before a federal grand jury after being subpoenaed in March 1929. When he finally appeared and testified, federal agents arrested him for contempt of court. Capone posted bond and was released, only to be arrested in Philadelphia that May on charges of carrying concealed weapons. Capone served nine months in prison and was released for good behavior.
In February 1931, a federal court found Capone guilty on the contempt charge and sentenced him to six months in Cook County Jail. Meanwhile, the U.S. Treasury Department had launched an investigation of Capone for income tax evasion. Through diligent forensic accounting, Special Agent Frank Wilson and other members of the Intelligence Unit of the Internal Revenue Service were able to put together a case, and in June 1931 Capone was indicted for evasion of federal income tax. Convicted that October after an internationally publicized trial, Capone was sentenced to 11 years in prison, first in Atlanta and later at Alcatraz. He was released in 1939 and died an invalid recluse at his Florida home in 1947.
On February 14, 1929, St. Valentine's Day, five members of the North Side Gang, plus gang collaborators Reinhardt H. Schwimmer and John May, were lined up against the rear inside wall of the garage at 2122 North Clark Street, in the Lincoln Park neighborhood of Chicago's North Side, and executed. Two of the shooters were dressed as uniformed police officers, while the others wore suits, ties, overcoats and hats, according to witnesses who saw the "police" leading the other men at gunpoint out of the garage after the shooting. John May's German Shepherd, Highball, who was leashed to a truck, began howling and barking, attracting the attention of two women who operated boarding houses across the street.
One of the women, Mrs. Landesman, sensed something was wrong and sent one of her roomers to the garage to see what was upsetting the dog. The man ran out, sickened at the sight. Frank Gusenberg was still alive after the killers left the scene and was rushed to the hospital shortly after police arrived at the scene. When the doctors had Gusenberg stabilized, police tried to question him but when asked who shot him, he replied "Nobody shot me", despite having sustained fourteen bullet wounds.
George Moran was the boss of the long-established North Side Gang, formerly headed by Dion O'Banion, who was murdered by four gunmen five years earlier in his flower shop on North State Street. Everyone who had taken command of the North Siders since O'Banion's rule had been murdered, supposedly by various members or associates of the Capone organization. This massacre was allegedly planned by the Capone mob in retaliation for an unsuccessful attempt by Frank Gusenberg and his brother Peter to murder Jack McGurn earlier in the year and for the North Side Gang's complicity in the murders of Pasqualino "Patsy" Lolordo and Antonio "The Scourge" Lombardo – both had been presidents of the Unione Siciliane, the local Mafia, and close associates of Capone. Bugs Moran's muscling in on a Capone-run dog track in the Chicago suburbs, his takeover of several Capone-owned saloons that he insisted were in his territory, and the general rivalry between Moran and Capone for complete control of the lucrative Chicago bootlegging business were probable contributing factors to this incident.
The plan was to lure Bugs Moran to the SMC Cartage warehouse on North Clark Street. Contrary to common belief, this plan did not intend to eliminate the entire North Side gang – just Moran, and perhaps two or three of his lieutenants. It is usually assumed that they were lured to the garage with the promise of a stolen, cut-rate shipment of whiskey, supplied by Detroit's Purple Gang, also associates of Capone. However, some recent studies dispute this, although there seems to have been hardly any other good reason for so many of the North Siders to be there. One of these theories states that all of the victims (with the exception of John May) were dressed in their best clothes, which would not have been suitable for unloading a large shipment of whiskey crates and driving it away – even though this is how they, and other gangsters, were usually dressed at the time. The Gusenberg brothers were also supposed to drive two empty trucks to Detroit that day to pick up two loads of stolen Canadian whisky.
On St. Valentine's Day, most of the Moran gang had already arrived at the warehouse by approximately 10:30 AM. Moran was not there, having left his Parkway Hotel apartment late. As Moran and one of his men, Ted Newberry, approached the rear of the warehouse from a side street they saw the police car pull up. They immediately turned and retraced their steps, going to a nearby coffee shop. On the way, they ran into another gang member, Henry Gusenberg, and warned him away from the place. A fourth gang member, Willie Marks, was also on his way to the garage when he spotted the police car. Ducking into a doorway, he jotted down the license number before leaving the neighborhood.
Capone's lookouts likely mistook one of Moran's men for Moran himself – probably Albert Weinshank, who was the same height and build. That morning the physical similarity between the two men was enhanced by their dress: both happened to be wearing the same color overcoats and hats. Witnesses outside the garage saw a Cadillac sedan pull to a stop in front of the garage. Four men, two dressed in police uniform, emerged and walked inside. The two fake police officers, carrying shotguns, entered the rear portion of the garage and found members of Moran's gang and two gang collaborators, Reinhart Schwimmer and John May, who was fixing one of the trucks. The "police officers" then ordered the men to line up against the wall.
The two "police officers" then signaled to the pair in civilian clothes who had accompanied them. Two of the killers opened fire with Thompson sub-machine guns, one containing a 20-round box magazine and the other a 50-round drum. They were efficient, spraying their victims left and right, even continuing to fire after all seven had hit the floor. The seven men were ripped apart in the volley, and two shotgun blasts afterward all but obliterated the faces of John May and James Clark, according to the coroner's report.
To give the appearance that everything was under control, the men in street clothes came out with their hands up, prodded by the two uniformed police officers. Inside the garage, the only survivors in the warehouse were Highball (May's German Shepherd) and Frank Gusenberg. Despite fourteen bullet wounds, he was still conscious, but died three hours later, refusing to utter a word about the identities of the killers.
Since it was common knowledge that Moran was hijacking Capone's Detroit-based liquor shipments, police focused their attention on the Purple Gang. Mug shots of Purple members Jim Carrey, Fletch, Ryan Van Wart and his younger brother Harry, were picked out by landladies Mrs. Doody and Mrs. Orvidson, who had taken in three men as roomers ten days before the massacre; their rooming houses were directly across the street from the Clark Street garage. Later, these women wavered in their identification, and Fletcher, Lewis, and Harry Keywell were all questioned and cleared by Chicago Police. Nevertheless, the Keywell brothers (and by extension the Purple Gang) would remain ensnared in the massacre case for all time. Many also believed what the killers wanted them to believe – that the police had done it.
On February 22, police were called to the scene of a garage fire on Wood Street where a 1927 Cadillac Sedan was found disassembled and partially burned. It was determined that the car had been used by the killers. The engine number was traced to a Michigan Avenue dealer, who had sold the car to a James Morton of Los Angeles, California. The garage had been rented by a man calling himself Frank Rogers, who gave his address as 1859 West North Avenue – which happened to be the address of the Circus Café, operated by Claude Maddox, a former St. Louis gangster with ties to the Capone organization, the Purple Gang, and a St. Louis gang called Egan's Rats. Police could turn up no information about anyone named James Morton or Frank Rogers. But they had a definite lead on one of the killers. Just minutes before the killings, a truck driver named Elmer Lewis had turned a corner only a block away from 2122 North Clark and sideswiped what he took to be a police car. He told police later that he stopped immediately but was waved away by the uniformed driver, whom he noticed was missing a front tooth. The same description of the car's driver was also given by the president of the Board of Education, H. Wallace Caldwell, who had also witnessed the accident. Police knew that this description could be none other than a former member of Egan's Rats, Fred 'Killer' Burke; Burke and a close companion, James Ray, were well known to wear police uniforms whenever on a robbery spree. Burke was also a fugitive, under indictment for robbery and murder in Ohio. Police also suggested that Joseph Lolordo could have been one of the killers, because of his brother Pasqualino's recent murder by the North Side Gang.
Police then announced that they suspected Capone gunmen John Scalise and Albert Anselmi, as well as Jack McGurn himself, and Frank Rio, a Capone bodyguard. Police eventually charged McGurn and Scalise with the massacre. John Scalise, along with Anselmi and Joseph 'Hop Toad' Giunta, were murdered by Capone in May 1929, after Capone learned about their plan to kill him, and before he went to trial. The murder charges against Jack McGurn were finally dropped because of a lack of evidence and he was just charged with a violation of the Mann Act: he took his girlfriend, Louise Rolfe, who was also the main witness against him and became known as the "Blonde Alibi", across state lines to marry.
The case stagnated until December 14, 1929, when the Berrien County, Michigan Sheriff's Department raided the St. Joseph, Michigan bungalow of “Frederick Dane”, the registered owner of a vehicle driven by Fred "Killer" Burke. Burke had been drinking that night, rear-ended another vehicle and drove off. Patrolman Charles Skelly pursued, finally forcing Burke off the road. As Skelly hopped on the running board he was shot three times and died of his wounds later that night. The car was found wrecked and abandoned just outside of St. Joseph and traced to Fred Dane. By this time police photos confirmed that Dane was in fact Fred Burke, wanted by the Chicago police for his participation in the St. Valentine's Day Massacre.
When police raided Burke's bungalow, they found a large trunk containing a bullet-proof vest, almost $320,000 in bonds recently stolen from a Wisconsin bank, two Thompson submachine guns, pistols, two shotguns, and thousands of rounds of ammunition. St. Joseph authorities immediately notified the Chicago police, who requested that both machine guns be brought there at once. Through the then relatively new science of forensic ballistics, both weapons were determined to have been used in the massacre – and that one of Burke's Tommy guns had also been used to murder New York mobster Frankie Yale a year and a half earlier. Unfortunately, no further concrete evidence would surface in the massacre case. Burke would be captured over a year later on a Missouri farm. As the case against him in the murder of Officer Skelly was strongest, he was tried in Michigan and subsequently sentenced to life imprisonment. Burke died in prison in 1940.
Public outrage over the St. Valentine's Day Massacre marked the beginning of the end to Capone's influence in Chicago. Although Moran suffered a heavy blow, he still managed to keep control of his territory until the early 1930s, when control passed to the Chicago Outfit under Frank Nitti, who had taken control of the Capone organization after Capone's conviction for income tax evasion. The massacre also brought the belated attention of the federal government to bear on Capone and his criminal activities.
In 1931, Capone was convicted of income tax evasion and was sentenced to eleven years in a Federal institution, plus one year in the Cook County Jail for attempted jury tampering. The massacre ultimately affected both Moran and Capone and left the war they had with each other at a stalemate. It was a blow from which the North Side Gang never fully recovered. But the most serious blows to both gangs, as well as most others around the country, was the Stock Market Crash in October 1929, which heralded the Great Depression, and the repeal of the 18th Amendment (Prohibition) in 1933, which had given rise to most of the lawlessness in the first place. Although McGurn beat the charges, he would later be shot dead in a Chicago bowling alley on February 14, 1936. The two most widely accepted theories blame either Bugs Moran or the Chicago Outfit itself under Frank Nitti with the killing, as McGurn had become a liability.
On January 8, 1935, Federal Bureau of Investigation (FBI) agents surrounded a Chicago apartment building at 3920 North Pine Grove, looking for the remaining members of the Barker Gang. A brief shootout erupted, resulting in the death of bank robber Russell Gibson. Also taken into custody were Doc Barker, Byron Bolton, and two women. While interrogating agents got nothing out of Barker, Bolton (a hitherto obscure criminal) proved to be a "geyser of information", as one crime historian called him. Bolton, a former Navy machine-gunner and associate of Egan's Rats, had been the valet and sidekick of a slick Chicago hit man named Fred Goetz aka Shotgun George Ziegler. Bolton was privy to many of the Barker Gang's crimes and even pinpointed the Florida hideout of Ma and Freddie Barker (both of whom were killed in a shootout with the FBI a week later.) To the agents' surprise, Bolton kept on talking and claimed to have taken part in the St. Valentine's Day Massacre with Goetz, Fred Burke, and several others.
Because the FBI had no jurisdiction in a state murder case, they attempted to keep Bolton’s revelations confidential, until the Chicago American newspaper somehow got their hands on a second-hand version of the bank robber’s confession. The newspaper declared that the crime had been “solved”, despite being stonewalled by J. Edgar Hoover and the Bureau, who did not want any part of the massacre case. Garbled versions of Bolton’s story went out in the national media. Pieced together, his tale went like this: Bolton claimed that the murder of Bugs Moran had been plotted in “October or November” 1928 at a Couderay, Wisconsin resort owned by Fred Goetz. Present at this meet were Goetz, Al Capone, Frank Nitti, Fred Burke, Gus Winkeler, Louis Campagna, Daniel Serritella, William Pacelli, and Bolton himself. The men stayed two or three weeks, hunting and fishing when they were not planning the murder of their enemies.
Byron Bolton claimed he and Jimmy Moran were charged with watching the S.M.C. Cartage garage and phoning the signal to the killers at the Circus Café when Bugs Moran arrived at the meeting. Police had indeed found a letter addressed to Bolton in the lookout nest (and possibly a vial of prescription medicine). Bolton guessed that the actual killers had been Burke, Winkeler, Goetz, Bob Carey, Raymond "Crane Neck" Nugent, and Claude Maddox (four shooters and two getaway drivers). Bolton gave an account of the massacre different from the one generally told by historians. He claimed that he saw only “plainclothes” men exit the Cadillac and go into the garage. This indicates that a second car was used by the killers. One witness, George Brichet, claimed to have seen at least two uniformed men exiting a car in the alley and entering the garage through its rear doors. A Peerless sedan had been found near a Maywood house owned by Claude Maddox in the days after the massacre, and in one of the pockets was an address book belonging to victim Albert Weinshank. Bolton further indicated he had mistaken one of Moran’s men to be Moran, after which he telephoned the signal to the Circus Café. When the killers (who had expected to kill Moran and maybe two or three of his men) were unexpectedly confronted with seven men, they simply decided to kill them all and get out fast. Bolton claimed that Capone was furious with him for his mistake (and the resulting police pressure) and threatened to kill him, only to be dissuaded by Fred Goetz.
His claims were corroborated by Gus Winkeler's widow, Georgette, in both an official FBI statement and her memoirs, which were published in a four-part series in a true detective magazine during the winter of 1935–36. Georgette Winkeler revealed that her husband and his friends had formed a special crew used by Capone for high-risk jobs. The mob boss was said to have trusted them implicitly and nicknamed them the “American Boys”. Byron Bolton’s statements were also backed up by William Drury, a maverick Chicago detective who had stayed on the massacre case long after everyone else had given up. Bank robber Alvin Karpis later claimed to have heard secondhand from Ray Nugent about the massacre and that the “American Boys” were paid a collective salary of $2,000 a week plus bonuses. Karpis also claimed that Capone himself had told him while they were in Alcatraz together that Goetz had been the actual planner of the massacre.
Despite Byron Bolton’s statements, no action was taken by the FBI. All the men he named, with the exceptions of Burke and Maddox, were all dead by 1935. Bank robber Harvey Bailey would later complain in his 1973 autobiography that he and Fred Burke had been drinking beer in Calumet City at the time of the massacre, and the resulting heat forced them to abandon their bank robbing ventures. Claude Maddox was questioned fruitlessly by Chicago Police, and there the matter lay. Crime historians are still divided on whether or not the “American Boys” committed the St. Valentine’s Day Massacre.