Mystery: The Saint Valentine's Day Massacre

Valentine’s Day has often been referred to as a “Hallmark holiday”. A day when people have excuses to either make candy bracelets, buy schmaltzy cards, or bouquets of roses for their significant other. Suffice to say, I’m not a fan of the holiday, but to each their own.

That said, there is another side to this oh-so beloved (and loathed) holiday that I do happen to love. It’s a day that lives on in infamy and legend in Chicago. A time when law didn’t rule, but rather crime did. It’s an event known only as the Saint Valentine’s Day Massacre and today marks the 90th anniversary of what is often called the most legendary Mob hit job. So let’s dive into this story and both learn about it and the theories as to who the hitmen were.

The date: February 14th. Valentine’s Day, 1929. At 10:30 A.M., four men, two of them dressed as police officers while the other two wore suits, ties, overcoats and hats, entered a garage at 2122 North Clark Street, which was a part of the Lincoln Park neighborhood in the north side of Chicago. Within the garage were seven men that belonged to the ruthless North Side Gang headed by George “Bugs” Moran; the arch rival to the legendary “Scarface” Al Capone. The two men had been at war with each other for control of Chicago and neither would ever accept responsibility for what would happen in the North Clark Street garage.

Gunfire rang out; the sounds of Tommy Guns and shotgun blasts ripping through the air. When silence finally returned, the so-called “policemen” lead the two suited men out at gunpoint and sped off, leaving the inside of the garage littered with bullet casings and the mangled bodies of the seven men; five members of Moran’s gang: his second-in-command and brother-in-law, Albert Kachellek (who sometimes went by his alias: James Clark) and the North Side’s bookkeeper and business manager, Adam Heyer. Enforcers and brothers Frank and Peter Gusenberg were also shot. Albert Weinshank, who was managing several cleaning and dyeing operations for the North Side Gang, was yet another victim.

The other two shot were collaborators with the North Side Gang: Reinhart H. Schwimmer, who was a gambler and associate of the gang, and John May, who was a mechanic for them. May’s dog, Highball, was also present and unharmed. All of the men—save for John May—were dressed in their best clothes, a custom of the North Side Gang and other gangsters during that time period.

When law enforcement arrived on the scene, all but one of the victims was alive: Frank Gusenberg. EMTs managed to stabilize him for a short period of time, but all he would tell police when questioned was, “No one shot me”.  Three hours later, he died from the fourteen bullet wounds and blood loss that came from said wounds.

Back at the crime scene, police looked over at what was left for them to discover. It was immediately apparent that whoever perpetrated the crime knew what they were doing. The hit was clean and well executed. The actual hit itself was a different story. The men had been lined up against a wall and mowed down by Tommy Gun fire—two in total were confirmed to have been used—and a few had their faces blown off by shotgun blasts.

Crime scene photos.

Immediately, police had a suspect: Al Capone. His long standing feud with Moran at the time of the massacre had hit its zenith after a shootout between his gang and the North Side Gang wherein over a thousand rounds were exchanged between the two gangs. That, plus numerous other skirmishes that the two gangs had, including one where Frank Gusenberg attempted to murder Jack McGurn earlier that year, made it clear that Capone wanted nothing more than for Moran to be killed.

This wouldn’t be the first time a North Side Gang leader was killed by Capone either. Every leader following Dean O’Banion, who was gunned down in his flower shop, was killed by members of Capone’s gang, the Chicago Outfit, but Moran managed to elude him. Following the massacre, Moran was quoted as saying, “Only Capone kills like that.”

In response, Scarface had this to say: “The only man who kills like that is Bugs Morgan.” We’ll get more into this later.

As for Capone’s plan, police theorized that Capone, driven by the aforementioned events plus the losses of Pasqualino “Patsy” Lolordo and Antonio “The Source” Lombardo—both of who were presidents of the “Unione Siciliana” and close to Capone himself—wanted to bait Moran, and a few of his lieutenants, to the warehouse with the promise of whiskey as supplied by the Purple Gang, which operated out of Detroit and was associated with Capone. Meanwhile, the Gusenberg brothers were to drive to Detroit and pick up Canadian whiskey.

Then, on the morning of the massacre, Moran’s gang arrived at the warehouse. However, Moran himself wasn’t there. Rather, he left his apartment late. Whether or not this was because he was skeptical of the meet-up or merely overslept is unknown. Nonetheless, when he arrived, he saw a police car near the building and immediately turned away, instead opting to go to a coffee shop. Along the way, they encountered Henry Gusenberg and advised him to turn away on. Yet another member, Willie Marks, also saw the car and left, but not before writing down the license plate number.

On the opposite side of things, Capone's lookouts wrongly identified one of the North Side members as Moran. With that, the massacre began; the two “police officers” and suited men entering the garage, lining then up against a wall, and mowing them down, even after all seven men were lying on the ground.

All things considered, the theory sounds air tight: Capone was sick of Moran's presence in Chicago and wanted him out. The only problem is there was no definitive way to pin it on him and even after Elliot Ness and his “Untouchables” went him to Alcatraz for tax evasion, nothing ever emerged that could tie Capone to the massacre.

Even still, the investigation continued. Initially, police turned their attention to the aforementioned Purple Gang, to which a few landladies were able to pick out a few men that they saw on the morning of the massacre: George Lewis, Eddie Fletcher, Phil Keywell and his younger brother, Harry. In spite of all four being questioned and subsequently cleared, the Keywell brothers remained persons of interest; by extension, the Purple Gang too.

A little over a week after the massacre, police got a break through in the case. A 1927 Cadillac Sedan was found in a garage that was ablaze on Wood Street. Although it was partially burned and had been disassembled, they were able to to determine that not only had it belonged to the killers, but they were able to trace the engine number to a dealer on Michigan Avenue. The owner told police that he had sold it to a man by the name of “James Morton” who claimed to be from Los Angeles. As for the garage, it was being rented by a man who called himself “Frank Rogers”. Rogers also gave his address, which was 1859 West North Avenue. This piqued the interest of police as that was the address of the Circus Café, which was run by a man named Claude Maddox; a gangster from St. Louis and had ties to not only Capone, but the Purple Gang and Egan’s Rats—which operated out of St. Louis.

Although the address proved to be promising, police weren’t able to figure out who either James Morton or Frank Rogers were. However, that would prove to not be necessary. A truck driver by the name of Elmer Lewis came forward and told authorities that mere minutes before the massacre took place, he sideswiped a police car and stopped. However, the officer, who Lewis noticed was missing a front tooth, waved him away. Backing up Lewis’ story was the H. Wallace Caldwell, who was the president of the Board of Education.

This tip set off alarm bells in the heads of police as there was only one man in the Chicago area who fit the description given: former Egan’s Rats member Fred “The Killer” Burke, a man who, along with James Ray, was known to don police uniforms and go on robbery sprees, and was missing a front tooth. Around this time, it was also theorized that the brother of Pasqualino Lolordo—Joseph—may have been involved to extract revenge on the North Side Gang for his brother’s death.

While the hunt for Burke went on, a few suspects were publicly named: John Scalise and Albert Anselmi, Jack McGurn, and Frank Rio. Scalise and Anselmi were both gunmen for Capone, while Rio was a bodyguard for Scarface himself. Of the four named suspects, McGurn and Scalise were charged with the massacre. However, Scalise and Anselmi, along with Joseph “Hop Toad” Giunta, were whacked by Capone in May of that year. As it would turn out, the three men planned kill Capone. It’s claimed that after he discovered their plot, he threw a dinner party in their honor and that at the end of his, Capone brought out a baseball bat and beat them all to death.

As for McGurn: the charges against him were dropped on account of a lack of evidence. Instead, he was charged with a violation of the “Mann Act” because he took his girlfriend, Louise Rolfe, out of state to marry. Rolfe was also the main witness against him. McGurn would later be murdered at the age of 33. His murder, just like this one, remains unsolved.

With their suspects either dead, free due to a lack of evidence, or not yet in custody, the case went cold until December 14, 1929. It was on this day that the Berrien County, Michigan Sheriff’s Department raided a bungalow in St. Joseph, Michigan that belonged to a one “Fredrick Dane”. Inside the bungalow, police found a large trunk that held a bullet-proof vest, $320,000 in bonds that had been stolen from a bank in Wisconsin, two Thompson submachine guns, pistols, two shotguns, and thousands of rounds of ammunition.

As for Dane, he happened to be the owner of a vehicle that was driven by Fred Burke and as it turned out, Burke was out drinking that same name and rear-ended another vehicle before driving off. A patrolman by the name of Charles Skelly promptly pursued Burke and managed to force him off the road, but was shot three times as he hopped onto the running board, and died later that night from his wounds.

As for Fred Dane, it turned out he was Fred Burke.

When St. Joseph authorities notified Chicago police, they requested that both of the Tommy Guns be brought to them at once thanks to the new science that was ballistics testing; both weapons proved to be a match to not only the massacre, but also in the murder of Frankie Yale, a mobster from New York who partook in the murder of Dean O’Banion.

Although the ballistics matched, Chicago police weren’t able to prove that Burke was responsible or present at the massacre itself and as such, when Burke was captured a year later on a farm in Missouri, he was sent back to Michigan where he was sentenced to life in prison for the murder of Officer Skelly. He died in 1940.

From 1929 until January of 1935, the case sat cold until agents from the Federal Bureau of Investigation got into a standoff with the remaining members of the Barker Gang. After a shootout, Doc Barker, Byron Bolton and two unnamed women were taken into custody. Russell Gibson however was killed during the shootout.

When being interrogated, Barker was as stubborn as a mule and didn’t speak. Bolton, a former Navy machine gunner and associate of Egan’s Rat’s, on the other hand was, as a crime historian put it, “geyster of information”. A valet for Fred Goetz, who was a hit man from Chicago, Bolton gave the FBI the location to both Ma and Freddie Barker (both of who were killed in a shootout with the FBI not long after) and claimed to have been a part of the massacre.

In spite of the large amount of evidence provided by Byron, the FBI lacked jurisdiction in Illinois and thus couldn’t do anything. That is, until the newspaper “Chicago American” reported on the robber’s confession, proudly claiming that the crime had been solved, despite then-director J. Edgar Hoover and the rest of the Bureau not wanting any part of the case.

To diverge for a bit, I want to touch upon something: the FBI back during this time, and especially under the leadership of J. Edgar Hoover, operated more like the mafia than it did as a law enforcement agency. Hoover was notorious for being very questionable in his tactics and was worse when it came to actually pursuing justice when it was warranted. FBI agents were known to take bribes from mobsters to turn a blind eye when it came to shady dealings and murders and some even had questionable trials. In the event that Hoover had sent the FBI to assist in the investigation, it’s unlikely anything would have changed considering the horrendous reputation the agency had.

In spite of the FBI’s unwillingness to pursue the case, the mainstream media picked up on the story and ran with it like it was the truth straight from Capone’s mouth. It was claimed that Bolton had said that the murder of Moran was plotted in either October or November of 1928 at a resort in Couderay, Wisconsin owned by Goetz. Those present at this supposed meeting were Goetz, Capone, Frank Nitti, Burke, Gus Winkeler, Daniel Serritella, William Pacelli, Louis Campagna, and Bolton. All of the men stayed there for a few weeks, hunting and fishing in between the plotting of the murder of their enemies.

Bolton went on to state that while he didn’t know who the shooters were, he believed they were Goetz, Burke, Winkeler, Bob Carey, Raymond "Crane Neck" Nugent, and Claude Maddox. All told, there were four shooters and two getaway drivers. Bolton also claimed that he and another man were tasked with monitoring the garage and giving the signal to the shooters, who were at the Circus Café, when Moran arrived at the meet. Corroborating this claim was that law enforcement had found a letter that was addressed to Bolton at the lookout nest.

From here however, Bolton’s claim began to steer in a different direction from the one that’s normally been given by historians. He stated that he only saw men dressed in “plain clothes” exist the Cadillac and enter the garage; indicating that there was a second car that was used by the gunmen. A witness by the name of George Brichet stated that he had seen at least two men in police uniforms exit a car in an alleyway before they entered the garage via its rear doors.

In the days following the massacre, a Peerless sedan was found near a Maywood house that was owned by Claude Maddox. In one of its pockets was an address book that belonged to Albert Weinshank, which Bolton said that he had mistaken one of Moran’s men for Moran himself; likely Weinshank himself. After mistaking Weinshank, or another one of the men, for Moran, he telephoned the killers, who were apparently surprised when confronted when the seven men. Being the quick thinkers that they were, the gunmen decided to go ahead and just mow them all down and get the hell out of dodge. Bolton then claimed that Capone was pissed at him for his mistake and threatened to kill him, but Fred Goetz persuaded him to let Bolton live.

If there was any doubt surrounding Bolton’s claims, they were potentially thrown out when Winkeler’s widow, Georgette, stated both to the FBI and in her memoirs that her husband, Gus, had made a special crew that Capone used for particularly difficult jobs; nicknamed the “American Boys”, Capone entrusted those within it to do whatever job he gave them and them alone.

Georgette’s statements weren’t the only backing that Bolton’s claims had. William Drury, a maverick detective from Chicago who kept investigating the massacre long after every other detective had either given up or died, stated that Alvin Karpis said he heard that Nugent that those within the “American Boys” were paid a collective salary of $2,000 a week, plus any potential bonuses. Karpis went on to say that while in Alcatraz, Capone personally told him that Goetz was the mastermind behind the massacre.

Yet, in spite of all of Bolton’s claims and the corroborating statements from Georgette and Drury, along with the evidence that supported Bolton, the FBI opted to take no action whatsoever. Everyone that Bolton named, save for Burke and Maddox, had died by 1935 for an assortment of reasons, and it would be a mere five years before Burke was croak.

In an autobiography released in 1973, Harvey Bailey—a bank robber—later claimed that he and Burke were out drinking in Calumet City while the massacre was taking place. He also stated that the ensuing heat from the event forced both of them to drop their bank robbing ventures. Exactly how Burke got possession of the weapons used in the massacre remains a mystery.

Claude Maddox was repeatedly questioned by Chicago police and that was all she wrote there; Maddox never coughed up an iota of evidence and took whatever he knew to the grave.

To this day, historians remain divided as to whether or not the “American Boys” were the perpetrators behind the massacre.

With no conclusive evidence pointing towards those associated with Capone as the killers, some have come to wonder if Capone was perhaps right about when he said that, “The only man who kills like that is Bugs Moran”. Indeed, there are those—both back then and even nowadays—who think Morgan himself ordered the hit. It was common for mob bosses to whack their own for an array of reasons, be they a mole, rat, or broke some sort of code. In this case however, the reasoning behind Moran doing this is questionable at best and outright doesn't exist at worst.

Some theorize that perhaps Moran wanted to pin the murders on Capone in homes of swaying business partners from working with him, while others believe Moran had the seven men killed because they were rats or any other of untrustworthy type of person. This, while not implausible, has nothing to back it up, but it remains an odd theory. Likely to make the feud between Capone and Moran all the more grandiose and fantastical.

The Saint Valentine's Day Massacre remains a staple in the sordid history of early twentieth century American history. A few of the bricks that were damaged by the gunfire during the massacre now reside in Las Vegas’ Mob Museum, while others were auctioned off after the garage itself was torn down. As for the case, it remains officially unsolved.

Two bricks from the garage that are now on display; the upper one at the National Museum of Crime and Punishment and the lower at Ripley;'s Believe it or Not.

All information was found via Wikipedia and was used to write this, but I reworded it so nobody can whack me for copying stuff, right? Ah well. Happy Valentine's Day everyone!