A Valentine For Bugs Moran: Part Two

Published July 23, 2021
A Valentine For Bugs Moran: Part Two
The Suspects

In the minds of many Chicagoans, the St. Valentine’s Day Massacre was the selesai blow to the city’s already-bloody reputation. Mortified and angry, the Chicago Association of Commerce (which had founded the Chicago Crime Commission in 1919) posted a reward of $50,000 for the arrest and conviction of the killers. Finally having had enough of the mobsters in their midst, 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.

But no agency wanted a swifter solution to the case than the police department because many people believed just what the killers wanted them to believe: that police officers had carried out the murders. This was the kind of reputation that the Chicago Police Department had earned by the end of the 1920s – a corrupt, scandal-ridden, law-breaking organization. Even the local Prohibition direktur, Frederick D. Silloway, spoke out against the department. “The murderers were not gangsters,” he said. “They were Chicago policemen. I believe the killing was the aftermath to the hijacking of five hundred cases of whiskey belonging to the Moran gang by five policemen six weeks ago on Indianapolis Boulevard. I expect to have the names of these five policemen in a short time. It is my theory that in trying to recover the liquor the Moran gang threatened to expose the policemen and the massacre was to prevent the exposure.”

Russell, by that time police commissioner, was likely unsure about what illegal activities many of his men were involved in, joined in: “If it is true that coppers did this, I’d just as soon convict coppers as anybody else.” Chief of Detectives John Egan added, “I’ll arrest them myself, toss them by the throat into a cell, and do my best to send them to the gallows.”
The next day, Silloway retracted the accusation that he made against the department, claiming that he had been misquoted. To ease tensions with the police, his bosses in Washington transferred him to another district. By then, however, the damage was done and suspicions lingered for many years.
The investigation proceeded under John Egan, the state’s attorney’s staff and Cook County Coroner Dr. Herman N. Bundeson, each working different angles of the case. Egan and his men searched the SMC Cartage Company warehouse and recovered the empty .45-caliber machine-gun cartridges.

Police detectives re-enact their version of the massacre's events for newspaper reporters during the investigation that followed the murders.

Assistant State’s Attorney Walker Butler and his detectives canvassed the neighborhood and found two corroborating stories at 2119 and 2125 North Clark Street, rooming houses run by Mrs. Michael Doody and Minnie Arvidson. Ten days before the massacre, three young men showed up, looking for rooms to rent along North Clark Street. Mrs. Doody was able to accommodate two of them and Mrs. Arvidson took in the third. They said that they were 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. When either landlady went in to clean, the tenant was almost always at the window, looking outside. All three of them vanished on the morning of the massacre. Butler suspected that the Purple Gang was somehow involved in the murders and he showed the landladies photographs of sixteen members. They identified three of them as the mysterious lodgers. But when questioned, at Butler’s request, by the Detroit police, all three of the men produced unshakable alibis, people who swore that they had been nowhere near Chicago.
On February 22, a fire broke out in a garage behind a house at 1723 North Wood Street, about three miles west of the crime scene. The firemen who answered the call discovered a black Cadillac touring car that had been partially demolished by an acetylene torch, axes and hacksaws. The torch, it was believed, had accidentally started the blaze and the men wrecking the vehicle had fled before its destruction was complete. Egan examined the remains of the Cadillac and the still-legible engine number allowed him to trace the car to Cook County Commissioner Frank Wilson, who had sold it to an auto dealership on Irving Park Road. The car dealer stated that he had then sold the car in December to a man identifying himself as “James Morton of Los Angeles.”

The chopped-up and burned remains of the car that were found in the North Wood Street garage -- just around the corner from the headquarters of Capone allies, the Circus Gang.

From the owner of the Wood Street property, a neighborhood grocer, Egan learned that a man who gave his name as “Frank Rogers” had rented the garage on February 7. He gave his address as 1859 West North Avenue, which was right around the corner. The house was now deserted but, significantly, it adjoined the Circus Café, the headquarters of Claude Maddox and the Circus Gang, whose ties to Capone, the Purple Gang and Egan’s Rats of St. Louis were well known. Even more significant was the fact that one of Maddox’s gang members, “Tough” Tony Capezio, had recently been badly burned in a fire. It has been suggested that Capezio had been cutting up the car to get rid of evidence and had accidentally started the fire by using the acetylene torch too close to a can of gasoline. The police could never prove it, however.

Another member of the Circus Gang at the time was Tony Accardo, who, according to a police theory formed later, helped plan the massacre. Soon after, he became a Capone gunman and was often seen seated in the lobby of the Lexington Hotel with a Tommy gun across his knees. Most likely, however, Accardo was not directly involved in the murders. He was a small-time member of the gang in those days and was likely tasked with disposing of evidence with Capezio and others.

Unable to pin anything on Maddox and his men, the police continued searching for the elusive “James Morton” and “Frank Rogers” but no trace of them were ever found. As for George Moran, he refused to disclose anything about the hijacker who had telephoned him on the night before the massacre, other than that he had known him for a long time and planned to “pay him back” for his treachery.

The police only had theories, but they developed one that they believed was accurate:

Al Capone knew about the massacre and had requested it, leaving the rencana to others. Jack McGurn certainly took part in the rencana, as did Jake Guzik, who spoke frequently with Capone from the Congress Hotel. The plan that was conceived called for two men who could persuade their victims to surrender their weapons without a fight, which was the reason behind the police uniforms. These men had to be total strangers to the Moran men, which meant that they had to be imported (likely by Maddox) from either Detroit or St. Louis. They were kept hidden until needed and then provided with the phony police car.

The function of the three Clark Street lodgers was to watch for Moran in exactly the same way that earlier Capone gang ambushes had been carried out. The killers were then informed by telephone when Moran entered the warehouse. What saved Moran’s life was his resemblance to Al Weinshank. Believing that Moran had already arrived, the lookouts gave the word to the killers.

The collision with the truck on Clark Street suggested the route that 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 men wearing civilian clothes probably waited in the garage’s front office while their uniformed companions relieved the Moran gang of their weapons. After that, they emerged with Tommy guns and ordered the seven men to face the wall. Even though the killers may have realized by then that Moran was not there, they didn’t dare let the others live since it’s possible that they recognized the men in civilian clothing. The killers then staged their selesai scene to confuse any witnesses as they reappeared on the street posing as policemen after a raid with their prisoners.

The investigators may have figured out the methods of the massacre, but debate raged as to the reasons behind it and just who might have been involved – debate that continues to this day.

Crime historians have named the most likely suspects (even though they number more than the actual number of killers – everyone has their own opinion) as:

Fred “Killer” Burke
Fred Burke, who was born Thomas Camp on a farm near Mapleton, Kansas, in 1893, was an armed robber and contract killer who was responsible for many crimes during the Prohibition era. He first ran afoul of the law at the age of 17 after being duped into participating in a land fraud scheme by a traveling salesman who had befriended his family. Fleeing his home in disgrace, he ended up in Kansas City and became involved with the underworld. By 1915, he was in St. Louis and joined up with the infamous Egan’s Rats.

Fred "Killer" Burke

Under an indictment for forgery, Burke (as he had become known) enlisted in the military at the start of World War I. He served as a tank sergeant in France. After returning home, he was arrested in Michigan for fraud and sentenced to a year in prison, followed by another year behind bars in Missouri for his earlier forgery case.
In early 1922, he rejoined Egan’s Rats, along with his best friends, fellow St. Louisians and war veterans Gus Winkler, Bob Carey and Raymond “Crane Neck” Nugent. Burke and his pals were suspected of robbing a St. Louis distillery of $80,000 worth of whiskey in April 1923. During the robbery, Burke disguised himself as a police officer to fool the security guards. He also plotted and carried out the robbery of the United Railways office, the city's streetcar provider, on July 3, 1923. The heist netted $38,000.

After the Egan’s Rats gang fell into disarray with the imprisonment of its leadership in 1924, Burke and his friends moved to Detroit, where they began committing robberies in the region and carrying out contract murders for the Purple Gang. Burke was suspected of introducing the Tommy gun to Detroit’s underworld in March 1927 when he used on to kill three rival gangsters who were suspected of killing his friend, Johnny Reid.

By the summer of 1927, the relationship between Burke’s crew and the Purple Gang had cooled. Burke accused gang boss Joe Bernstein of killing his friend Ted Werner in New Orleans on April 16 and the gang claimed that Burke was kidnapping Purple Gang associates for ransom. The feud turned bloody on July 21 when Burke was accused of machine-gunning a number of gang members as they exited a bar on Oakland Avenue. Three men were wounded and one, Henry Kaplan, was killed. Joe and Abe Bernstein sent word that they wanted to iron out a peace treaty with Burke and Gus Winkler at a downtown Detroit hotel but Burke sent Raymond Shocker in his place – who was almost killed in an ambush.

After the falling out with the Purple Gang, Burke moved his crew to Chicago, where they joined up with Capone’s organization. Burke and Winkler, especially, grew close to the Chicago crime boss, who referred to them fondly as his "American Boys."

Over time, Fred Burke and his crew were suspected of robbing banks and armored cars in St. Louis, Louisville, New Jersey, Wisconsin, Michigan, Indiana, Los Angeles and Ohio. The Ohio job, on April 16, 1928, resulted in the murder of a Toledo police officer. Burke and his partners were also linked by ballistic evidence and informants to the murder of Brooklyn mob boss Frankie Yale in July 1928. 

The Burke crew became the leading suspects in the St. Valentine’s Day Massacre and Burke was even named publicly as a suspect by the Chicago Police in the weeks after the murders. Burke has never been “officially” linked to the massacre but he was convincingly fingered by Byron “Monty” Bolton in 1935.

Bolton was an expert machine-gunner in the U.S. Navy before turning to a life of crime and kidnapping and stated that the rencana for the massacre was carried out at a resort owned by Fred Goetz on Cranberry Lake, six miles north of Couderay, Wisconsin, in October or November of 1928. Capone was present, as was Gus Winkler, Burke, Goetz, Louis “Little New York” Campagna and William Pacelli, a North Side politician who was later elected to the Illinois state senate. Bolton also involved Claude Maddox in the plot. Bolton himself claimed to be one of the lookout men on Clark Street, a claim that seems backed up by the fact that a medicine bottle and a letter, both with his name on them, were found in one of the rooming houses during the neighborhood canvass. Bolton claimed that Burke and Fred Goetz were the men disguised as police officers during the massacre and Maddox, Carey and Winkler were the shooters in plain clothes.

Bolton was under arrest in St. Paul, Minnesota, for the ransom kidnapping of Edward Bremer, along with members of the Barker Gang, when he made the confession. Informed of his statement, Chicago police captains John Stege and William Shoemaker, probably the most honest crime fighters in the city during the Prohibition periode, believed Bolton. “The first suspect I sent for was Maddox,” Shoemaker said. “I felt sure he was one of the executioners but I could not prove it. I had to let him go.” Lieutenant Otto Erlanger of the homicide bureau added that he thought Bolton’s story was “true in every word.”

Bolton's claims were later corroborated by Gus Winkler's widow, Georgette. Bank robber and Barker Gang member Alvin Karpis later endorsed Bolton's story to Capone biographer John Kobler.

But not everyone was convinced. FBI director J. Edgar Hoover, who had Bolton in custody on the federal kidnapping charge, dismissed his claims. He stated that the massacre was a “Chicago matter for the local police to resolve.” Claude Maddox was brought in for another round of questioning in 1935 but he was let go. Nothing was done to follow up on the story and as the press lost interest, it faded away and was mostly forgotten.

As for Fred Burke, his downfall came after he hit a motorist in St. Joseph, Michigan, on December 14, 1929. Burke had been drinking and tried to flee the scene. A police patrolman named Charles Skelly overtook him and forced him to the curb. As Skelly jumped onto the car’s running board, Burke shot him three times and sped away. Skelly died at the hospital and Burke’s car was found on U.S. Highway 12, cracked up against a telephone pole. The registration papers in the glove compartment bore the name “Fred Dane” and listed an address on the outskirts of St. Joseph. When police raided the bungalow, they found a bulletproof vest, bonds recently stolen from a Wisconsin bank, two Thompson submachine guns, pistols, and thousands of rounds of ammunition. Ballistics tests conducted by nationally renowned expert Calvin Goddard revealed that both of Burke's Tommy guns had been used in the St. Valentine's Day massacre. The same tests showed that one of them had been used to murder gangster Frankie Yale -- a murder allegedly arranged by Capone. 

The arsenal found inside of Burke's home included two tommy-guns that were used in the St. Valentine's Day Massacre and one that had been used to kill mobster Frankie Yale. 

Burke became America’s most wanted man but he didn’t stay on the run for long. He managed to elude the police for just over a year, until he was arrested at a farm near Green City, Missouri, on March 26, 1931. The Chicago authorities wanted him for his possible role in the massacre but Michigan refused to surrender him, preferring to try him for the murder of Patrolman Skelly. He was sentenced to life imprisonment at the Michigan State Penitentiary and died there of heart disease at the age of 47.

Fred “Killer” Burke is the only man who has been tied by evidence to the massacre, but he certainly didn’t act alone and the list of his possible accomplices is a long one.

Fred Samuel Goetz
Goetz, also known as “Shotgun” George Zeigler, was a long-time mobster who was also believed to have been involved in the massacre. Born in Chicago, the son of German immigrants, he was stationed at Langley Field, Virginia, during World War I and served as a pilot in the U.S. Army’s aviation branch, where he rose to the rank of second lieutenant. After graduating from the University of Illinois, in 1922, Goetz worked as a lifeguard at Clarendon Beach until he was charged with sexually assaulting seven-year-old Jean Lanbert, after luring her into an alley with a promise of candy. Goetz denied the charges and jumped bail on June 10, 1925. Four months later, Roger Bessner implicated Goetz in the failed robbery of Dr. Henry R. Gross, in which the family driver was killed.

During the next several years, Goetz would become associates with underworld figures such as Joseph "Yellow Kid" Weil and Morris Klineman, as well as participating in several armed robberies, including the robbery of $352,000 from the Farmers and Merchants Bank, in Jefferson, Wisconsin, with Fred Burke, Gus Winkler and others, in 1929. His connections with Burke and his crew possibly led to his inclusion in the massacre hit squad. According to Byron Bolton, he was one of the men dressed as police officers.

After the massacre, Goetz left Chicago and began bootlegging operations in Kansas City, Missouri before becoming associated with the Barker Gang. He later participated in several bank robberies with Alvin Karpis, Fred and Doc Barker and took part in the kidnapping of St. Paul millionaire Edward Bremer in 1933. Goetz was the gang member who collected the ransom and released Bremer.

Goetz was killed on March 20, 1934. He had returned to Chicago and was murdered in a drive-by shooting outside of a closed Cicero restaurant, the Minerva. The murder remains unsolved, although a number of his former associates, including the Barker Gang, had reasons to kill him. Alvin Karpis believed that Outfit boss Frank Nitti ordered the murder.

Robert Carey
Born in St. Louis, Carey joined the Egan’s Rats gang when he was in his early twenties. By 1917, he had become close friends with Fred Burke and after serving in the Army during World War I, continued on as a low-level associate in Egan’s Rats. At this time, while Burke was serving prison time, Carey became associated with a Cincinnati gunman called Raymond “Crane Neck” Nugent. Both men were suspected of robbing a Cincinnati bank messenger in December 1921 and trying to fence the bonds through the Egan's Rats.

Carey was known for being exceptionally smart but he was also an alcoholic who took great risks and became violent when he drank. In spite of this, he was the mastermind behind the St. Louis distillery robbery and Fred Burke’s policeman disguise in 1923.

After the collapse of Egan’s Rats in 1924, Carey went with Burke to Detroit and was arrested in March for the robbery of the John Kay jewelry store. While Carey was suspected of being part of the crew, only Isador Londe was convicted of the crime and received a 10- to 20-year sentence.

Cary continued to run with Burke and his crew through the 1920s. He was specifically charged by the Detroit authorities for the murder of two freelance gunmen, James Ellis and Leroy Snyder, on March 16, 1927, after he caught them cheating at poker. On April 16, 1928, Carey, along with Winkler, Goetz, Nugent and Charlie Fitzgerald, took part in an American Express armored car robbery in Toledo, Ohio. The robbers made off with $200,000 and a Toledo cop named George Zientara ended up dead.

Even though he was never publicly named as a suspect, Carey was sought by the Chicago police after the St. Valentine’s Day Massacre. Nothing could be pinned on him, although Byron Bolton did name him as one of the men involved.

With most of his closest associates locked up or dead by early 1932, Carey left Chicago for the East Coast. He and his girlfriend, Rose, ended up in Baltimore, where they began blackmailing well-to-do businessmen and politicians. The marks would bed Rose and Bob would discreetly take pictures. This operation had dead-ended by summer and they moved north to New York. Carey, now using the alias of Sanborn, rented a flat on 104th Street and started a high-quality counterfeiting racket. Despite his newfound success, Carey was drinking heavily – with fatal results. According to NYPD reports, on the night of July 29, 1932, a drunken Carey went berserk and shot Rose to death, after which he turned the gun on himself.

Ray "Crane Neck" Nugent
Ray Nugent was born in Cincinnati around 1895 and came to St. Louis during the heyday of Egan’s Rats. He managed to talk himself into the gang’s good graces and became friends with fellow war veteran Bob Carey. Nugent was heavily built, with a strong jaw, muscular shoulders and no neck to speak of. For reasons that no one can fathom (except, perhaps, irony), he was nicknamed “Crane Neck.” Although no one actually called him that, the moniker followed him on police records for the rest of his life. Ray also sometimes used the alias “Gander.” He and Carey shared similar voracious appetites for booze and violence.

Nugent also became closely associated with other suspected massacre gunmen like Burke, Winkler and Goetz and took part in the distillery robbery in April 1923. When the remnants of the gang left St. Louis for Detroit in 1924, Nugent went with them. He was involved in a number of robberies with elements of Burke’s crew, including a home invasion on Halloween night 1926. Nugent, Carey and another crew member named Tony Ortell broke into the home of real estate broker Edward Loveley and made off with about $40,000 in diamonds, furs, and antiques. Carey and Nugent, identified from mug shots, dumped the loot and fled west to Los Angeles, where they were arrested on suspicion of robbing a jeweler. Both were extradited to Detroit to stand trial for the Loveley caper but the charges didn’t stick.

In the spring of 1927, Nugent, Carey and Gus Winkler kidnapped popular Detroit gambler Mert Wertheimer with plans to bring in a six-figure ransom. They drove him to Chicago and kept him in a North Side apartment on Grace Street. It turned out that Wertheimer was not only protected by the Purple Gang but was also a good friend of Al Capone. Winkler and his wife, Georgette, had just moved into the Leland Hotel when Winkler was contacted by an emissary of Capone, who wanted to have a meeting.

Knowing that Wertheimer was stashed only a couple of blocks away, Winkler nervously told Carey and Nugent that Capone wanted to meet with them. Not surprisingly, they had no interest in accepting an invitation to their own murder and wanted nothing more than to get out of Chicago as soon as possible. Winkler talked them into coming with him to the meeting and, hoping to make a good impression on the crime boss, cleaned up his partners and gave them a crash course in manners.

In May 1927, the three men met with Capone at the Hawthorne Inn in Cicero. Capone was his often-charming self and explained to his guests how the kidnapping racket was no place for talented men. He suggested that they get into a real business. Winkler enjoyed the evening chatting with Capone but, to his dismay, both Nugent and Carey drank too much and began talking loudly and laughing. Surprisingly, Capone ignored their antics and generously offered the three men some cash to replace the ransom that they were going to lose by releasing Wertheimer. Winkler declined but his pals eagerly snatched up the money. Shaking his head, he was pleased about how the evening had gone but less than thrilled with the behavior of Nugent and Carey.

Mert Wertheimer was immediately released and Carey and Winkler settled in Chicago. Nugent went back to Ohio where his wife, Julia, was living with their two children. His partners began hanging around Capone, hoping to ingratiate themselves with the mob boss and his men. Capone began calling the crew his “American Boys” and after the almost disastrous robbery in Toledo, he gathered them all back to Chicago.

Nugent became one of the leading suspects in the massacre, mostly because of the company that he kept and the fact that he was dangerously violent. Many believe that he was one of the plainclothes killers, who machine-gunned the North Side gang members to death.

After the massacre, Nugent remained a low-level member of the Capone gang. In April 1930, he was arrested for drunk driving with Ralph Capone in the Miami area. About a year later, Nugent disappeared. Rumor had it that he had become a liability to the Outfit and had been taken out into the Everglades and fed to the alligators. Whatever happened, he was never again seen. In 1951, his wife filed a petition in Cincinnati to have him legally declared dead so that she could claim his pension as the widow of a World War I veteran.

Gus Winkler
Born August Henry Winkeler in St. Louis in 1901, Winkler was a member of the St. Louis-based Cuckoo Gang during his teenage years. After a stint as an Army ambulance driver in World War I, Winkler joined up with the Egan's Rats before moving to Detroit with Burke and the other remnants of the gang in 1924.

Gus Winkler

Working with the Purple Gang until 1927, he and Burke were often hired out for freelance work and began their own crime spree holding up banks, armored cars, and mail trucks. After moving to Chicago, Winkler and the others began working almost exclusively for Al Capone and are believed to have been directly involved in the massacre. It is widely believed that Winkler was the fifth man in the murder team, the one waiting behind the wheel of the black Cadillac while the others murdered the North Side gang members.
Winkler and Burke's crew broke up during the fallout from the St. Valentine's Day Massacre, and Winkler was suspected of rencana and later taking part in the robbery of two million dollars from a bank in Lincoln, Nebraska in September 1930. However, he gave evidence against his partners and returned his share of the loot in exchange for clemency, damaging his reputation in the underworld. In spite of this, he was able to carve out a lucrative position in the rackets of Chicago’s North Side, mostly based on the close friendship that he had maintained with Capone.

Upon Capone's 1931 imprisonment, Winkler was surrounded by gangsters who didn't trust him, in particular Frank Nitti. However, he still remained a force in post-Capone Chicago, controlling rackets on the North Side independent from the Outfit.

In June 1933, a close friend of Winkler’s, Verne Miller, was accused of helping gun down three policemen and a federal agent in an attempt to free bank robber Frank Nash during the Kansas City Massacre. Winkler, who was trying to sever ties with the violent end of the business so that he could concentrate on his gambling and nightclub operations, was seen going into the Banker’s Building office of Melvin Purvis, the head of the FBI’s Chicago field office, likely to give him a tip on where to find Miller. The fact that Winkler seemed to be getting cozy with the cops again – once a snitch, always a snitch, in the standard underworld credo – was too much for Frank Nitti to handle.

At 1:40 p.m. on October 9, 1933, as Winkler was going into the beer distribution office of Charles Weber at 1414 North Roscoe Avenue, a green delivery truck cruised by and its occupants opened fire with shotguns. Winkler was hit with 72 shotgun pellets and succumbed to his wounds a half-hour after arriving at a local hospital. He managed to gasp out the Lord’s Prayer before he died. His murder remains officially unsolved. 

Claude Maddox
“Screwy” Claude Maddox was born John Edward Moore in St. Louis in 1897. Little is known about him prior to his founding of the Circus Gang, which had a beer and booze concession on the western edge of Dion O’Banion’s territory during Prohibition. His headquarters, the Circus Café, was a dive kafetaria on North Avenue and would figure prominently in the theories regarding the massacre. Maddox was a former member of Egan’s Rats and for this reason, he welcomed Burke and his crew to the city and likely offered them assistance covering things up after the massacre. If Byron Bolton’s story is to be believed, Maddox also took part in rencana and carrying out the murders.

After the black Cadillac touring car that had been driven by the massacre killers was found in the burning garage on Wood Street, the police traced the renter of the garage, “Frank Rogers,” to an address that adjoined the Circus Café. The kafe was jointly owned by Maddox and “Tough Tony” Capezio, who had recently suffered burns. Detectives were excited about what they saw as a new lead, connecting the massacre to the Circus Gang. In addition, the address given by “Frank Rogers” was also directly across from the apartment of the late Patsy Lolordo and had apparently been used as an indoor shooting range. The café itself had been recently closed and was being stripped of its fixtures, but at the address listed by “Rogers,” police found guns and overcoats flung down in such a way that seemed to indicate that the occupants had fled in a hurry as soon as the garage caught on fire.

Maddox had very basic living quarters at the café, but he had given his home address as 1642 Warren Avenue on the West Side. He had a reputation as a Capone man, his territory offering a safe place between the Aiellos in Little Italy and Moran on the North Side. Members of the Circus Gang included gunmen like Jack McGurn, Tony Accardo, Rocco de Grazia and assorted hoods from the “Patch,” an area of fluctuating boundaries on the West Side that comprised nearly a dozen different European immigrant communities. It was also a hangout for Maddox’s St. Louis friends, Al Capone’s so-called “American Boys.”

Maddox was almost immediately suspected as being part of the massacre, but the cops could never make anything stick. After Byron Bolton’s 1935 confession, he was picked up once again but investigators had to let him go since Hoover and the FBI refused to cooperate with the Chicago police.

Maddox stayed involved with the Outfit after Capone went to prison and his effectiveness in union racketeering spared him the fate of Gus Winkler when Frank Nitti began cleaning house in the early 1930s. Those skills, along with his partnership in a semi-legal gambling equipment firm, allowed him to rise high in the mob before his death in 1958. Maddox quietly passed away at his Riverside, Illinois, home – one of the few men connected to the massacre who did not die a violent death.

The theories about who was involved in the St. Valentine’s Day Massacre are as numerous as the theories as to why the massacre took place. There have been scores of theories put forth by crime historians over the years and just about any of them can make sense if they are presented in just the right way. Many of them are preposterous and impossible and others seem to make a cunning bit of sense. Logically, the massacre was ordered by Capone (but planned by his henchmen) in an effort to eliminate George Moran and bring an end to the harassment by the North Side gang once and for all.

There were a number of reasons why Capone would want Moran and his gang out of the way, not the least of which was the constant hijacking of Capone’s liquor trucks and the undercutting of his business interests in the city. It could have also been retribution for the murders of Tony Lombardo and Pasqual Lolordo, Capone’s presidents of the Unione Siciliane. Moran’s backing of Joe Aiello would have also increased Capone’s hatred for the man. Capone was also being hampered by Moran in his takeover of the Cleaners’ and Dyers’ Association, which was a powerful racket into which Capone wanted to expand. There was also the matter of revenge for the attempted murder of Jack McGurn by the Gusenbergs, something that likely figured into McGurn’s thoughts as he helped plan the massacre.

The massacre was a simple, cold-bloodedly efficient assassination that was meant to kill George Moran and break the back of the North Side gang, opening up its territories and operations to Al Capone. While the identities of the killers will most likely always remain a mystery – the reason behind the massacre has never seemed very puzzling.

In spite of this, many writers feel the need to try and shock the public with alternate theories or bizarre twists that really don’t seem to be backed up by the historical evidence. For instance, one claim was that the men were not gathered at the garage that day to await a liquor shipment, but to discuss the presence of a   traitor in their midst and take action against him. It was suggested that Moran would not have come to the warehouse for a mere liquor shipment. However, this angle does not hold up when one takes into account the fact that Moran was a “hands-on” gang manager who often took delivery of shipments. In addition, he was supposed to be there because his presence had been specifically requested by a hijacker whom he knew and trusted. Moran railed against this man so often in the newspapers after the massacre that it’s unlikely that he didn’t exist. It’s also unlikely that Reinhart Schwimmer – essentially a “gangster groupie” – would have been allowed to hang around the garage that day if such an important meeting was going to be taking place. 

Perhaps the most ridiculous theory is one that received some attention in recent years. It asserted that Capone had nothing to do with the massacre at all – that it was a revenge killing by a low-level gunman who was looking to avenge his cousin. The theory was based one of the hundreds of crackpot letters that were received by the police and the FBI after the massacre. This particular letter had been sent by Frank Farrell in January 1935. Farrell, who had a patronage job in the state highway department, wrote about his connection to William Davern, Jr., a former fireman who was shot in a gangster hangout called the C&O Cabaret and Restaurant at 509 North Clark Street. Davern died a month later from his wounds – but not before allegedly getting some startling information. According to Farrell’s letter, William “Three-Fingered Jack” White, who was a cousin of Davern, told Davern (who was visiting him at the county jail) that Davern had been shot by one of the Gusenbergs. In retaliation for Davern’s shooting, White lured the Gusenbergs to the garage at 2122 North Clark Street and then killed them, along with everyone else inside. Farrell waited several years and then sent the information in a letter to the FBI.

While an interesting story, the tale in the letter has a number of fatal flaws. Despite a 2010 book that touted it as the “solution” to the massacre mystery, most historians dismissed the letter (which was easily accessible in the files of the case) because it has no credibility. One of the biggest problems with the letter theory is that it does not explain how Fred Burke ended up with the Tommy guns that were used in the massacre (one of which had killed Frankie Yale in 1928). It also doesn’t explain the need for Byron Bolton as a lookout (remember that physical evidence placed him at the scene), or why Claude Maddox and his gang disposed of the car involved, or most of the other known facts in the case. 

The letter also confuses names and basic details of the case, such as how people are related to one another. For example, Davern’s mother was not the sister of Jack White’s father. Davern’s mother, born Anna Gillespie, was the sister of White’s mother, Mary Gillespie.

Another persoalan is that, according to the Chicago Police Department, the leading suspect in the fatal shooting of William “Billy” Davern was Jack McGurn. This means that if one of the Gusenberg brothers, or some other North Side gang member, did not shoot Davern, then White would have no reason to kill them in revenge. According to a newspaper account, Davern was likely involved in the March 1928 attempt on McGurn’s life.

It should also be noted that Davern was so serious after being shot that he lingered in the hospital until he died in December 1928, fighting for his life the entire time. It is highly unlikely that he could have gone to the Cook County Jail so that White could tell him that he had been shot by one of the Gusenbergs.

This brings us to the most important problem of all: according to newspaper and police reports, Jack White was in the Cook County Jail when the St. Valentine’s Day Massacre took place. White was sent to jail in 1926, without bond, for his part in the murder of a police officer. He was not released until July 1929, when his conviction was overturned, months after the massacre took place. Therefore, White couldn’t have been out of jail killing anyone on February 14, 1929. 

How this theory has gained attention in recent times is more puzzling than trying to pin down who carried the Tommy guns into the SMC Cartage building that day. Cook County Coroner Herman Bundeson, who Farrell contacted before writing to J. Edgar Hoover, probably dismissed Farrell's letter as nonsense as soon as he checked the jail records. He rejected the letter as a fraud and so should anyone with a genuine interest in the case.  

Capone gunman, Jack "Machine Gun" McGurn

While Fred “Killer” Burke became a leading suspect in the massacre, he was far from the only one. Almost immediately after the murders, the Chicago police began “rounding up the usual suspects” and one of the first arrested was Jack McGurn. The warrant sworn out for McGurn’s arrest was based on the testimony of a young man named George Brichet who happened to be walking down Clark Street in front of the warehouse on February 14. As he was passing by, he saw the five killers enter and he heard one of them say “C’mon, mac.” He picked out McGurn’s photograph from a police rogue’s gallery and said that he recognized him. Many historians have questioned the identification, although they don’t doubt that Brichet heard what the man said correctly. In those days, “mac” was a casual way for someone to address a man, like “pal,” or “buddy.” It didn’t necessarily have to be someone’s actual name. Brichet heard it and repeated it to the cops, who saw it as a perfect excuse to roust McGurn, whom they felt was undoubtedly tied into the massacre somehow.

When the police showed up for McGurn, they found him at the Hotel Stevens with a blonde woman named Louise Rolfe. He was indicted for seven murders and his bail was set at $50,000. He raised that amount using a hotel that he owned that was valued at over one million dollars as collateral. McGurn said he was with Miss Rolfe when the killings took place, causing newspapermen to dub her “the Blonde Alibi.” He swore that he had never left her side at the Hotel Stevens between 9:00 p.m. on February 13 and 3:00 p.m. on February 14. The state’s attorney had him indicted for perjury but before McGurn could be tried on that charge, he married Louise Rolfe. A wife cannot be forced to testify against her husband.

Louise Rolfe, the bombshell that reporters dubbed the "Blonde Alibi." McGurn later married her so that she didn't have to testify against him in court. 

As the investigation into the massacre dragged on, McGurn’s lawyer began calling for his client to be brought to trial. Under Illinois law, if the accused demanded to be tried at four separate terms of court and the state was not prepared to prosecute him, the state had to dismiss the case. Between the spring and winter of 1929, McGurn made four demands for a trial. None of them were met and on December 2, he walked out of the courtroom a free man. By then, the authorities had revised their version of his role in the massacre and concluded that although he did not take part in the murders, he definitely had a role in their rencana. They had no evidence of this, however, and McGurn was never charged with anything relating to the crime.

Later, he and Louise were convicted of conspiring to violate the Mann Act, which prohibited interstate transport of women for “immoral purposes” when they were visiting Capone in Florida. The convictions were later overturned by the U.S. Supreme Court.

McGurn was not the only one arrested and indicted for having a possible role in the massacre.
During Coroner Bundeson’s inquest, he summoned every gun dealer in Cook County that he could find, including Peter von Frantzius, the reputed weapons source for all of Chicago gangland. He admitted that he had recently sold six Tommy guns to a man named Frank H. Thompson, who was allegedly acting as a buyer for the Mexican consul general, whose government wanted the weapons to help put down revolutionaries. The police knew that Thompson was an ex-convict, a safecracker, a hijacker and lately, an arms dealer. He was then wanted for attempting to machine-gun his wife and her lover in his hometown of Kirkland, Illinois.

Thompson surrendered to Bundeson. He admitted that he had purchased the guns but claimed that he had sold them to James “Bozo” Shupe, who was killed soon after. Shupe, detectives knew, was a close associate of Capone gunmen Scalise, Anselmi and Joseph Giunta, the current, Capone-backed president of the Unione Siciliane. With these thin connections, the police arrested the three Sicilians, mostly on the basis that if Capone had ordered something violent and bloody to be carried out, these men were probably involved. Giunta, with no actual evidence against him, was immediately released, but new witnesses placed Scalise and Anselmi in the fake police car. They were indicted and then released after posting a $50,000 bond.

Unfortunately, they didn’t live long enough to ever stand trial for the massacre murders.

Two days after Scalise, Anselmi and Giunta were arrested, the state’s attorney added four more names to the list of alleged assassins, bringing the total to seven, instead of five. The first was Joseph Lolordo, a natural suspect since his brother had been murdered in a plot likely engineered by Moran. During World War I, he had served with a detachment of machine-gunners and many believed he had been behind the actual murders. He had since disappeared. Another suspect was Frank Rio, a Capone bodyguard and gunman.

The disclosure of the third and fourth names followed eyewitness testimony furnished by prominent Chicagoan H. Wallace Caldwell, president of the board of education. Caldwell had been one of the witnesses to the accident on Clark Street between the truck and the Cadillac. As he glanced over, he happened to see that the driver in the police uniform was missing an upper front tooth. This distinguishing mark fit Fred “Killer” Burke and soon after, he became one of the most wanted criminals in the country.

The other indictment issued was for “James Ray,” alleged to be a constant companion of Burke. James Ray may have been an alias used by Gus Winkler or Ray Nugent, but a mug shot of Ray that was published in the March 6, 1929 edition of the Chicago Tribune shows a large, square-jawed man with hard eyes and thinning hair. “James Ray” was neither Winkler, Nugent, nor anyone else known to be in the Burke crew. His identity remains a mystery.

So, who really carried out the St. Valentine’s Day Massacre? Thanks to the ballistics evidence that tied Fred Burke to the crime, it seems likely that he and his former Egan’s Rats companions performed the hit at the behest of Al Capone. But for whatever reasons – indifference, corruption, or lack of hard evidence – the murders were never officially solved.

The St. Valentine’s Day Massacre marked the end of any significant gang opposition to Capone, but it was also the event that finally began the decline of Capone’s criminal empire. The massacre had simply taken things too far and the authorities – once content to let gangsters kill gangsters – and even Capone’s once-adoring public, were ready to put an end to the bootleg wars. The massacre started a wave of reform that would eventually send Capone out of power for good.

To be Continued...


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