The Valentine's Day Massacre

On February 14th, 1929, one of the most shocking murders in mob history goes down in Chicago... and becomes known as the Valentine’s Day Massacre. The 20s and 30s are full of gangland murders, but the Valentine’s Day Massacre is considered the most brutal, and the toughest to solve. So who carried out the Valentine’s Day Massacre? And why? Thank you to our experts who contributed to this episode: Clarence Goodman, Claire White, Natalia Mehlman Petrzela, Mike King, Cheryl Dorsey, and Larry Dale Gragg. If you’re new here, don’t forget to follow History’s Greatest Mysteries to never miss an episode! History’s Greatest Mysteries is a History Channel Original Podcast, brought to you by Rewind Studios. 🎧 Need More to Binge? Listen to other Rewind Studios Originals, Hidden History and Government That Doesn’t Suck, wherever you get your podcasts! Follow us on Social Instagram: @RewindStudios https://www.instagram.com/rewindstudiosTikTok: @RewindStudios https://www.tiktok.com/@rewindstudios See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

• 0:00Speaker 00

  And now, a History Channel original podcast presented by Rewind.

• 0:11Speaker 00

  Today, one of the most shocking murders in mob history, the Valentine's Day massacre.

• 0:17Speaker 01

  On February 14th, 1929, seven men from Bugs Moran's infamous gang are lined up against a wall and executed.

• 0:27Speaker 02

  There's 70 shots fired.

• 0:29Speaker 01

  Bugs Moran was supposed to be in that meeting, and he never came. And then he sat back in the wings and watched what happened.

• 0:38Speaker 03

  This level of violence was off the charts.

• 0:40Speaker 00

  The 1920s and 30s are full of gangland murders, but the Valentine's Day massacre will go down as both the most brutal and toughest to solve.

• 0:51Speaker 04

  They published incredibly gruesome images of this violence. And there's this immediate public outcry for justice. People want to know who did this and to see them brought in. But no one can really figure it out.

• 1:04Speaker 00

  Now, we explore the top theories surrounding the Valentine's Day massacre.

• 1:09Speaker 05

  The person with the most to gang when it comes to the death of Moran and the gutting of his gang is obviously Al Capone.

• 1:16Speaker 01

  He's quite direct. He says, "Gangsters did not do this. Cops did it."

• 1:22Speaker 03

  If this were a revenge killing over the son of a police officer, it would make sense why officers would then look the other way.

• 1:33Speaker 05

  Even though we're approaching a century since the Valentine's Day massacre, it is still one of the coldest cases in American history.

• 1:42Speaker 00

  Who carried out the Valentine's Day massacre, and why did they do it?

• 1:48Speaker 00

  Welcome to History's Greatest Mysteries, a History Channel original podcast presented by Rewind Studios. Each episode, we take a deep dive into some of the greatest unanswered questions from history, backed by some of the foremost experts on the subject. Today, the Valentine's Day massacre.

• 2:18Speaker 00

  January 16th, 1920, Chicago, Illinois. It's a Saturday night, and as midnight draws near, bar patrons take their last sips of legal alcohol. When the calendar flips, America is officially going dry.

• 2:35Speaker 05

  The Volstead Act, the dreaded 18th amendment, which has been brewing since the Industrial Revolution hit the United States, and suddenly, everybody's working a 40-hour work week. And alcohol is being blamed for absenteeism, tardiness. It's also, more importantly, being blamed for violence that men rain down on women.

• 2:59Speaker 02

  Prohibition is seen as a Christian cure-all for American bad behavior. They believe that this can end domestic violence, it can end poverty. This is something, they believe, will make the nation healthier, wealthier, and safer.

• 3:17Speaker 04

  So as the clock winds down on prohibition, you have kind of two energies taking hold of the American populace. You both have temperance advocates who are so excited that this new, more moral age in America is about to dawn. Then you have people who are rueing the fact that alcohol will no longer be available legally, and they're basically getting drunk on that last night. People talk about it as America's last call.

• 3:46Speaker 01

  There's no better way to create demand than to tell someone they can't have something. And essentially, what the government did is they immediately created a demand for alcohol that could not be satisfied any other way than through illegal means. And that was what the mob was built for. They were able to slip in and immediately start putting together networks of buying and selling alcohol and providing it to people.

• 4:15Speaker 04

  In this prohibition era, Chicago finds itself as a real hub. It's a big city, it's centrally located for distribution purposes. There's already a kind of notoriously corrupt law enforcement system. And so, all of this is kind of the perfect storm for it to be the place that Al Capone makes his name.

• 4:35Speaker 02

  Al Capone becomes the most important mob boss and the most important bootlegger in Chicago. He's actually Brooklyn-born. He moves to Chicago around 1920, and he takes what is already a pretty well-run gang, and he turns it into a million-dollar, money-making powerhouse.

• 4:58Speaker 00

  By some accounts, Al Capone's operation brings in $100 million a year, about $1.7 billion in today's money.

• 5:07Speaker 03

  There were actually two rival gangs at this time that were really vying for everyone's attention. There was the Chicago outfit, run by Al Capone, and the North Side Crew, which was run by George Bugs Moran. Bugs Moran earned the nickname Bugs because he was very violent, he was very volatile, and they kind of thought he wasn't all there. He was just kind of buggy.

• 5:31Speaker 00

  While Capone rules Chicago's South Side, Moran maintains a stronghold on the North Side, and by 1926, their rivalry turns into an all-out war.

• 5:43Speaker 01

  Bugs Moran and Al Capone couldn't stand that one might be growing faster than the other. And before long, we see Al Capone looking over his shoulder. In fact, he has a $50,000 bounty on his head that's bringing people from out of state in, trying to kill Al Capone.

• 6:03Speaker 05

  One of the tactics that was exclusively a Chicago thing was created by the North Siders, the marriage of the Thompson submachine gun to an eight-cylinder automobile. Absolutely devastating.

• 6:18Speaker 01

  So with this bounty on his head, Al Capone had an entourage of people who would travel with him, whose sole responsibility was to look out for something that would place him in danger. And that day came in a little restaurant in Cicero, near South Side Chicago. And Capone's eating when all of a sudden, a bunch of cars pull up. The windows come down, and men with Thompson submachine guns start spraying the building with bullets. More than 1,000 bullets were fired at Capone that day. And miraculously, this guy is able to escape unharmed.

• 6:59Speaker 04

  It's important to realize that even though these two men loomed so large, this was an era where petty criminality was everywhere. Everybody in Chicago seemed to be on the take at this time.

• 7:11Speaker 00

  The city's police force was notoriously corrupt. Even Chicago mayor William Hale Thompson was rumored to be in Al Capone's pocket.

• 7:19Speaker 04

  The public is kind of willing to turn a blind eye to some of this stuff. A lot of people felt that, you know, these guys can kill each other off. We don't really care. Just keep our booze flowing and keep us out of the crossfire.

• 7:31Speaker 00

  All that changes on the morning of February 14th, 1929, Valentine's Day.

• 7:38Speaker 02

  There is a meeting in a garage on the North Side, and there's seven members of the gang that are waiting for their boss, George Bugs Moran, to meet them. According to eyewitnesses in the neighborhood, they see a Cadillac pull up, and four or five men jump out of this Cadillac, two dressed in police uniforms, and they knock on the door of the garage. It's very likely that the seven men assembled in the garage thought that this was just a simple police shakedown.

• 8:11Speaker 01

  This was something that gangs were used to at that time. And frankly, if it's true that they owned the police through bribes and other kinds of things, it wasn't too stressful to go through the process, get arrested, and get bailed out, and the charges to be dropped. But this time, it was much different.

• 8:30Speaker 05

  So they are told, "Get against the wall, put your hands up." The ones who had weapons have their weapons relieved of them. The men from the Cadillac unsheathe their overcoats, pull out Thompson submachine guns and shotguns, and then they open fire.

• 8:58Speaker 02

  There's 70 shots fired. According to eyewitnesses, the perpetrators get back into the Cadillac and they speed off. People in the neighborhood know something has gone on. They've heard these shots. So a few brave souls go into the garage and discover what is clearly a horrific crime scene.

• 9:21Speaker 00

  Newspapers across the country pick up the story, dubbing it "The Valentine's Day Massacre."

• 9:27Speaker 04

  They published incredibly gruesome images of this violence. And if you can imagine, before this, people knew about the crime and the violence of the underworld, but it was very much sort of below the radar of what most people had in their face. Then, all of a sudden, you have this brutal act of violence and pictures of it in the newspaper.

• 9:47Speaker 05

  The usual suspects are rounded up, but no arrests were ever made. That stuck. Even though we're approaching a century since the Valentine's Day massacre, it is still one of the coldest cases, one of the most intriguing mysteries when it comes to crime in American history.

• 10:07Speaker 04

  There's this immediate public outcry for justice. People want to know who did this and to see them brought in. But no one can really figure it out. The rivalry between Bugs Moran and Al Capone is legendary. So when a group of Moran's men gets gunned down so violently, minds immediately go to one name.

• 10:26Speaker 00

  Bringing us to theory number one: the killer was Al Capone.

• 10:31Speaker 05

  The person with the most to gang when it comes to the death of Moran and the gutting of his gang is obviously Al Capone. Many people are certain that it's him because he has rumored to have already initiated, if you will, the deaths of maybe 200 people in Chicago, including a handful of men who have been Bugs Moran's predecessors.

• 10:54Speaker 02

  Bugs Moran is truly the only man standing in Al Capone's way of taking full control of Chicago. Even though Bugs Moran wasn't in the garage during the morning of the massacre, it completely hobbles Moran's operation.

• 11:08Speaker 00

  Moran himself publicly accuses Capone of orchestrating the massacre.

• 11:14Speaker 05

  As one would expect, Bugs Moran blames Al Capone and says words to the effect of "Only Capone kills like that." Many politicians and many people of note around the United States already believe that Al Capone is capable of doing anything. And so they tend to drift over into siding with Bugs Moran's interpretation of the events.

• 11:37Speaker 01

  Herbert Hoover had just been elected president. In his campaign, he spoke about bringing law and order back to the United States. And there was a focus on Capone. It was determined that he was a public enemy.

• 11:54Speaker 00

  In true Capone fashion, the notorious mob boss seems to have the perfect alibi.

• 12:00Speaker 02

  On the morning of the massacre, Capone is in Florida. He's living in his home on Palm Island in Miami. And that morning, he has a meeting with the DA to talk about his involvement with another murder, something that had happened the year before. It's impossible to put Capone at the scene of the massacre if he's clearly talking to law enforcement agents in Miami. Just because his alibi eliminates him from pulling the trigger, it doesn't eliminate his involvement. It's very possible he still pulled the strings.

• 12:35Speaker 03

  Some people believe the fact that Al Capone had such an airtight alibi, that this was part of the setup and probably means more so that he ordered the hit at a time when he knew he would not be there.

• 12:48Speaker 05

  So typically, part of the Capone plan was for there to be nothing that could tie him to the event, no matter how many layers he needed to use. Even if he had shot someone or beaten somebody's head in, he was never there.

• 13:05Speaker 02

  This was a highly planned, organized hit. And that sort of lends to the theory that it was put together by organized crime. But even though a good majority of people did think that this was a Capone orchestrated hit, it's not the only theory.

• 13:21Speaker 00

  It's the morning of February 14, 1929. Some Chicago residents have just heard a barrage of gunfire ring out at 2122 North Clark Street on gangster Bugs Moran's turf. As crowds gather outside the garage, Sergeant Thomas J. Loftus is the first policeman on the scene.

• 13:42Speaker 01

  Sergeant Loftus came in and saw this incredibly gruesome sight. As he checked each of the bodies to see if there was anyone alive, he came across one particular individual who'd been shot 14 times but was still clinging to life, a guy named Frank Guesenburgh. Sergeant Loftus leaned down and he whispered to him, "Who did this to you?" And Guesenburgh said, "The cops did it."

• 14:09Speaker 02

  Sergeant Loftus does try to get more information out of Guesenburgh. And allegedly, Guesenburgh says, you know, "Take me to the hospital. I need to be seen by a doctor." And he never gives away anything else. Although a lot of people immediately jumped to the conclusion that Capone was involved, once stories about Guesenburgh's words, as well as the fact that eyewitnesses saw people dressed in police uniforms coming in a Cadillac that looked like a police-issued vehicle, people start to question, and there are theories that maybe Chicago police were involved.

• 14:45Speaker 00

  That's theory number two: they were killed by corrupt cops.

• 14:55Speaker 04

  There are real elements of this crime scene that support this theory that cops did it. Some of the guys that ran out of the car were wearing police uniforms. And the Cadillac in which these guys drove up was of the sort that the police would outfit for use. It also had a weapons rack on the back, which was something only the police had.

• 15:15Speaker 00

  The accusation that corrupt police carried out the Valentine's Day massacre also comes directly from a member of law enforcement.

• 15:23Speaker 06

  Frederick Sillaway, who was the Chicago Assistant Prohibition Enforcement Administrator, a very long title, holds a press conference the next day. And he's quite direct. He says, "Gangsters did not do this. Cops did it." Which gets the press's attention immediately. And he said later in the day, "We'll be giving you the names of the cops involved."

• 15:50Speaker 05

  One thing he stated to emphasize this point, that it was easily rogue cops, is that they had the perfect disguise when it came to their misdeeds, this very, very public war between the Capone Organization and the Moran Organization.

• 16:08Speaker 00

  This shocking allegation makes headlines across the country.

• 16:12Speaker 06

  But there was no second press conference. And the next day, Sillaway has been moved to another district.

• 16:21Speaker 02

  There are so many corrupt law enforcement officers in Chicago during prohibition that people don't find this very hard to believe, but Chicago police claim that there is no proof of this. They say that the police uniforms that eyewitnesses saw were red herrings, that these were probably imposters. And there are a number of hitmen throughout the Midwest that used police uniforms in order to get away with their crimes.

• 16:47Speaker 05

  The idea that someone might have gone to the lengths to soup up a car or make uniforms is not as ridiculous and as far-fetched as it might sound. It would have been pretty easy for someone with the connections to come up with really authentic-looking police uniforms.

• 17:06Speaker 02

  Chicago police shut down their internal investigation almost immediately. They are not considering their own. And they make it very clear to the public that they don't want them considering police either. By shutting down their internal investigation so quickly, it leaves people with a bad taste in their mouth, and there's a lot of room for speculation.

• 17:28Speaker 00

  Three months after Chicago's notorious Valentine's Day massacre, the investigation goes cold. But then, 20 miles away, in the town of Hammond, Indiana, there's a gruesome discovery.

• 17:42Speaker 01

  Police come across an abandoned car and they look inside and there are two guys horribly murdered. They were just shot. They're completely disfigured. Then they found a third guy lying on the ground, same thing. If anything, it was even more brutal than the Valentine's Day massacre. The investigators are able to identify who these three butchered men were: John Scalise, Alberto Anselmi, and Joseph Junta.

• 18:14Speaker 05

  Even hardened coroners are absolutely dumbstruck by this scene because it looks like these three men have been bludgeoned with what appear to be baseball bats. Nose is broken, eyes bludgeoned, faces going both directions simultaneously. They're almost unrecognizable.

• 18:34Speaker 04

  The three men had noted ties to Capone. Junta was one of his henchmen, a hitman. And Anselmi and Scalise were known as the Sicilian Murder Twins.

• 18:46Speaker 05

  The Murder Twins were made mafia men who came to Chicago and they were Al Capone's favorite contractors. They would rub the bullets in garlic so if the hole didn't kill you, the infection would.

• 19:00Speaker 02

  In 1925, both John Scalise and Alberto Anselmi had taken part in a failed attempt on Moran's life. So there's history there. People had already connected these men to the massacre. They were questioned after the crime. Scalise and Anselmi were actually charged at one point, although there just isn't enough evidence to pin the crime on them.

• 19:20Speaker 00

  But now, three months after the massacre, these same gangsters have turned up dead.

• 19:27Speaker 05

  So these men turning up dead in the way in which they were killed, it's so brutal. It makes the authorities in Chicago start to say, hey, maybe these people were involved with the Valentine's Day massacre and they were actually the perpetrators. And this is the retaliation for that.

• 19:44Speaker 00

  Giving us theory number three: the killers were Capone lieutenants.

• 19:49Speaker 04

  Some newspaper reports indicated that Bugs Moran believed these were the men who had carried out the Valentine's Day massacre. And maybe this is comeuppance for that. Another theory is that this was almost a sacrifice that Capone made to make peace with Moran. In the months between the Valentine's Day massacre and the Hammond murders, there is this moment where there are peace talks between Moran and Capone and other organized crime figures. This much violence, this much attention from the police, from the press, it is not good for business. And so as bitter as the rivalry between Capone and Moran is, they know that it might actually serve them to kind of call a halt to these hostilities.

• 20:34Speaker 05

  Everybody wants peace. But Bugs Moran won't even come to the table unless the Southsiders turn over. Anselmi, Scalise, and Junta. He won't even attend any meetings. And so there's not going to be any peace. This is clearly personal for Bugs Moran. He wanted these guys gone because he felt that they were responsible for the massacre. So, funny enough, just five days after the Indiana murders, we not only have a peace conference, we have a peace conference that involves every big-time gangster in the United States, including Capone and Moran. So did Capone give the green light to kill these guys to settle the score? Possibly.

• 21:17Speaker 01

  As Americans are sort of getting used to the idea that Bugs Moran had called for the elimination of these three men outside Hammond, Indiana, the Chicago Tribune publishes an article that says, no. It wasn't Moran. It was Al Capone. And according to the story, Capone arranges for a dinner at the Plantation Restaurant just outside Hammond, Indiana. And Capone shows up with two objects, which most people think are large decanters of champagne. When he pulls away the tissue paper, it's two large clubs. Capone used those clubs to beat these men senseless and then shot them in the head.

• 22:01Speaker 02

  Capone killing his own associates is not all that uncommon in gangland Chicago. And there are these rumors that Scalise and Anselmi and Junta are starting to grow a little too big for their britches. Capone has been in hiding for so long and he's living primarily in Florida. So there's this potential that maybe these three men are leading a revolt back in Chicago. They're trying to take over the Southside Gang. And if that's the case, Capone's not going to let that happen. It's also possible that he was willing to sacrifice a few of his men in order to broker peace with Moran. In reality, all of these things could be true. If these three men were involved in the massacre,

• 22:47Speaker 02

  that goes with them to their graves. But it's not long before another mobster comes under suspicion.

• 22:53Speaker 00

  It's December 1929, nearly a year since seven of gangster Bugs Moran's associates were gunned down in the Valentine's Day massacre. And the case is still unsolved. By now, the tide is turning against gangsters and the rampant violence they cause. But without any hard evidence, investigators still can't crack the case. Then they get what might be their biggest break yet.

• 23:19Speaker 01

  In December, in the same year of the Valentine's Day massacre in Michigan, just about 100 miles north of Chicago, a man was driving his vehicle when he was involved in a collision. A patrol officer, who happened to be in the area, witnessed the accident and ordered both of the men to come to the police station. The policeman jumps on the running board of one of the vehicles. And as they're approaching the police station, they come up to a stoplight. And when they're fully stopped, the driver of this vehicle pulls out a revolver and shoots the policeman three times. Knocks him off the running board and he takes off. Crashes his car.

• 24:02Speaker 01

  And gets out and runs away.

• 24:08Speaker 05

  When the authorities go through the abandoned vehicle, they find documents regarding the ownership. And it is registered to a guy named Fred Dane. So using these documents, they go to the home of Fred Dane and they find something that they've never seen before, certainly not in the small town of St. Joseph.

• 24:28Speaker 01

  They discover a cache of automatic weapons, two Thompson submachine guns, grenades, shotguns. And along the way, they recover some physical evidence, fingerprints, that they're able to compare. And they learn at that point that Fred Dane is actually a man named Fred Killer Burke. Burke was actually kind of a sole entrepreneur, working on his own, sometimes for the mob, sometimes for himself. But he had a beef with Bugs Moran because it was Moran's men who actually hijacked some of his illegal shipments of alcohol,

• 25:12Speaker 01

  costing him a lot of money. And with that came, in his opinion, a desire to commit homicide.

• 25:21Speaker 00

  Leading to theory number four: they were killed by an angry hitman.

• 25:26Speaker 04

  Not only did Burke have a motive to strike back at Moran, he clearly had the means. He has a closet full of weaponry, including the same kind of weapons that were used in the massacre.

• 25:38Speaker 01

  The police enlisted the help of this incredibly brilliant scientist named Calvin Goddard. They asked Goddard if it was possible to compare the bullets recovered at the scene of the Valentine's Day massacre with bullets fired through the Thompson submachine guns in Burke's house. Inside of a barrel of a gun are these things called lands and grooves that create kind of a circular motion. Calvin Goddard wondered if he could scientifically examine bullets and see if they came from the same gun, thinking that those lands and grooves might actually be like a fingerprint, so to speak, that it would be very characteristic of just that weapon.

• 26:23Speaker 00

  Calvin Goddard examines the guns found at Fred Killer Burke's house, along with bullets recovered from the Valentine's Day massacre.

• 26:32Speaker 01

  Goddard does his testing and he reaches a stunning conclusion. All seven men killed in the Valentine's Day massacre were shot with those two Thompson submachine guns found in the closet of Fred Killer Burke.

• 26:50Speaker 06

  And this is really the first significant use of forensic ballistics. And it will become an incredibly important science.

• 27:00Speaker 01

  Killer Burke goes on the run for nearly a year. So he kind of becomes public enemy number one. And he actually becomes the subject of a lot of true crime stories that are being published. And then a man in Green City, Missouri, reads a story about Killer Burke in one of these true crime magazines. And he realizes that one of America's most wanted men resembles a guy who's living next door to him.

• 27:29Speaker 03

  The neighbor phoned in a tip. And he says, I think your guy is over here. I think he's my neighbor. Come take a look. And officers did just that. And they found Fred Killer Burke hiding in a farmhouse. And he was taken into custody without incident.

• 27:45Speaker 03

  So officers have Burke in custody, and they're very much concerned about making sure that the charge of having killed one of their own sticks. And so they're much more preoccupied with those charges than they really are about who killed a couple of gangsters. And witnesses can't identify him from the Valentine's Day massacre. He's already serving life for having killed a police officer. And you can't serve life more than once. And so it just kind of really goes by the wayside.

• 28:12Speaker 00

  Four years later, however, more evidence emerges connecting Fred Killer Burke to the massacre.

• 28:19Speaker 04

  A bank robber named Byron Bolton says he's got new information on the Valentine's Day massacre. He says Burke was the gunman and that he knows because he was a lookout there. Most importantly, Bolton says that the guy who ordered the hit was Al Capone. Bolton's claim makes headlines, but immediately it has holes in it. Two of these men that Bolton fingers both have airtight alibis. And then J. Edgar Hoover says, this is not true. Bolton is just making up a story in order to look like he's cooperating to get a reduced sentence.

• 28:51Speaker 00

  Ultimately, the authorities don't act on Bolton's allegation, leaving Fred Burke's involvement with the massacre unresolved.

• 28:59Speaker 01

  Burke dies in prison without ever telling what happened, either on Valentine's Day or anything surrounding the weapons. And with everything Al Capone is responsible for, it's interesting that in the end, the only thing that Hoover and his men can get are tax evasion charges, which ultimately send him to prison, where his health deteriorates so badly that he finally is released and returned to his home, and he later dies. In keeping with the mob code of silence, Al Capone took the secret to the grave.

• 29:36Speaker 00

  Coming up, turmoil in Bugs Moran's crew leads to a surprising theory.

• 29:42Speaker 02

  All of these incidences with Peter Guesenburgh make the Northside Gang look like a laughingstock, and Moran might have gotten fed up.

• 29:57Speaker 00

  It remains a mystery exactly why Bugs Moran's men were gathered in a Chicago garage on the morning of Valentine's Day, 1929. But there's at least one clue that leads historians to believe this was an important meeting.

• 30:12Speaker 02

  We may never know exactly why Moran's men were gathered in the garage that day, but we know that they were all dressed well. One even had a carnation in his lapel. It's Valentine's Day, so maybe they're dressed up for that. But it's more likely that they were there, dressed up for their boss, believing that this is going to be a business meeting. But Moran does not show up at the garage that day.

• 30:34Speaker 00

  Moran's absence and the lack of specifics about the meeting's purpose leads some to suggest an unconventional theory.

• 30:42Speaker 02

  The fact that Moran wasn't at the garage that day casts suspicion in his direction. There are questions that he calls this meeting, and yet he's so late that he's not there. Did he have ulterior motives?

• 30:55Speaker 00

  This is theory number five. They were killed by Moran.

• 31:00Speaker 01

  The thing that's so intriguing is Bugs Moran was supposed to be in that meeting, and he never came. In fact, he later would only say that he pulled up a little bit late, and he noticed the police car and the police officers walking in. So he went and sat at the nearby coffee shop as the murders unfolded. Essentially, he called the meeting, and then he sat back in the wings and watched what happened. Many have theorized that Moran may have done this to do a little house cleaning, that he might have had leaders within his organization that were starting to carve a new pathway.

• 31:40Speaker 01

  Maybe there was some infighting that was going on, or perhaps they were colluding to take over the organization and take it away from Bugs Moran.

• 31:52Speaker 06

  He had some rogue members of his organization, the Guesenburgh brothers. Frank and Peter were not always doing what he told them to do. They were his key hitmen, his key musclemen. But Peter in particular had gotten into the habit of pulling off what really were petty crimes. One example that the press liked to write about is that he robbed two very well-dressed women and stole their jewelry worth $14,000, which is an enormous amount of money in the 1920s. And then a really bizarre case, he tries to shake down a stockbroker. I'm aware of this fellow had a gun, and the guy began shooting his gun at Peter Guesenburgh, this tough, tough Bugs Moran hitman, and he runs away.

• 32:37Speaker 06

  And to Moran, this is unacceptable.

• 32:40Speaker 02

  All of these incidences with Peter Guesenburgh make the Northside Gang look like a laughingstock, and Moran might have gotten fed up. People who are critical of this theory say that it's unlikely that he would have taken out so many of his own men just to send a message to two. He's hobbled his own organization, if you believe this theory.

• 33:01Speaker 01

  After the Valentine's Day massacre, Moran's organization started to rapidly decompose. Moran tried to hang on to his position as a mob boss, but he quickly was being recognized by others in the criminal world as someone who couldn't perform any longer. He made attempts to join other mob organizations, and they simply said, your time has passed, and kind of brushed him off.

• 33:28Speaker 00

  By the 1940s, Moran's nearly broke. And after being arrested for robbery and mail fraud, he dies in prison in 1957.

• 33:38Speaker 02

  We will never know if Moran actually killed his own men, but it definitely would explain why he never showed up.

• 33:45Speaker 00

  Although a letter buried in the files of federal investigators suggests the massacre was payback. In 2010, Al Capone biographer Jonathan Igg discovers a 75-year-old letter in the FBI archives.

• 34:02Speaker 05

  This is a letter written by Frank Farrell. In it, he tells the director that if he wants truly to solve the St. Valentine's Day massacre, he should look into the fatal shooting of William Davenport. He says that in November of 1928, William Davenport, the son of a police officer, was in a Northside pub that was known as a gangster hangout. And he got into a skirmish with some people from Bugs Moran's crew, and he wound up beaten, shot, and left four dead.

• 34:34Speaker 02

  He's able to make it to a firefighter's call box, and he calls in this crime. He's taken to the hospital, and he lives for several weeks. But he does not tell anyone who shot him, with the exception, according to this letter, of his cousin, a man named William White, more commonly known as Three-Fingered Jack.

• 34:55Speaker 05

  Three-Fingered Jack is a lifelong criminal in Chicago. He knows all of the Northside gangsters. He's been in a number of stick-ups, big heists of payrolls and things of this nature. But he also has a hot temper, and he's been known to get really, really violent when necessary, particularly when it comes to family pride. When it came to his cousin, he swore vengeance.

• 35:21Speaker 00

  Taking us to theory number six. They were killed for revenge.

• 35:26Speaker 04

  Three-Fingered Jack had done some work with Moran's men, the Guesenburgh brothers. Back in 1926, Three-Fingered Jack and this crew, including the Guesenburgs, had robbed a factory of $80,000. When one of them snitched, Jack and another guy dressed up as policemen and murdered the snitch in his sleep. Of course, that detail links directly back to the Valentine's Day massacre, when multiple people saw the perpetrators dressed up as police before shooting up the place.

• 35:57Speaker 05

  Three Finger Jack knows plenty of crooked cops, including his uncle, who not only is a retired cop, but also the father of his murdered cousin, who can easily put him in touch with all of the things they need when it comes to fake police uniforms and the like. And so the plan appears to be that he will tell Moran to send all of his guys and himself over to the garage for another job. And the result is all of these men being killed.

• 36:28Speaker 03

  Coincidentally, the location of the Valentine's Day massacre, 2122 North Clark Street, is the exact same location where Three Finger Jack had done business with the Moran gang previously. So if he summoned them to that location, they would not have thought twice about it. When you look at the sheer brutality of the Valentine's Day massacre, it doesn't feel random. It feels very personal. It feels like they were really trying to send a message. So if this were a revenge killing for someone having killed the son of a police officer, it would make sense why officers would then look the other way.

• 37:09Speaker 06

  Is there any evidence whatsoever to link Three Finger Jack to this shooting? Well, one of the witnesses said, you know, the driver of the black Cadillac looked like he was missing a finger. So maybe there is some validity to this, but there is no genuine follow-up. In part because Three Finger Jack had been arrested. He was incarcerated on the day of Valentine's Day massacre. Maybe he bribed the police to let him out? That's highly unlikely. So even this theory that Frank Farrell comes up with, like all the others, has some holes in it.

• 37:45Speaker 00

  Ultimately, Hoover doesn't act on Farrell's tip. Some believe it's because Three Finger Jack was an informant for the FBI.

• 37:53Speaker 03

  And it would make sense that if Three Finger Jack is able to toss them a bone or two bad activity by other gangsters, that they might look the other way. I don't know how much value they really put on the life of somebody who was involved in the kinds of things that the North Side gang members were involved in. Maybe having them executed wasn't really causing any heartburn for law enforcement at that time.

• 38:23Speaker 05

  When it comes to Three Finger Jack, we'll never know, as he was shot in 1934. They took all of his secrets to the grave with him. The reason that so many gangland secrets have stayed a secret, and probably always will, is because there's always the implication, if not the out-and-out threat, of retaliation. It is assumed, and it is demanded, that one be silent.

• 38:47Speaker 04

  It's so hard to get to the bottom of this case because this is a world in which dishonesty is part of everyday activity, in which everybody's corrupt. Everybody has a side deal. People die very young. Violence eliminates people who might have shared something later in their life. And so I think that it is really difficult to ever really get a handle on what happened that day.

• 39:12Speaker 06

  There's two principles in this story. Bugs Moran and Al Capone lived several years after the Valentine's Day massacre. Capone, he would die at home almost two decades after this shooting. And Bugs Moran survives almost three decades after what happened in the garage that day. And what's intriguing about both these cases? No one was curious enough to ask either Capone or Bugs Moran what really happened. If they did ask them, no one ever recorded what the two men said. So we're left with this extraordinary mystery about America's coldest case almost a century later.

• 39:57Speaker 00

  Chicago in 1929 was so dominated by gangsters and corrupt officials. It's no wonder the truth about the Valentine's Day massacre remains shrouded in rumors and secrecy. Everyone had an agenda, one that often had nothing to do with justice. But interest in the most famous gangland hit of all time is still intense. Perhaps new evidence will emerge as we approach the massacre's 100-year anniversary. For now, though, it remains America's coldest case. Thanks so much for listening to History's Greatest Mysteries, a History Channel original podcast presented by Rewind Studios. Join us next time for a deep dive into another mystery

• 40:42Speaker 00

  and all the theories behind it.