Transcript

St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers

From American History Tellers · Episode page · Watch on YouTube

· 39 min · 6,948 words · 50 timestamped sections

This is the full, timestamped transcript of "St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers", an episode of American History Tellers published February 12, 2026 (39 min, about 6,948 words). It mentions 20 people, works and ideas, including Chicago, Al Capone, Johnny Torio, Haimey Weiss, George Bugs Moran.

What this episode is about

The St. Valentine's Day Massacre, which took place on February 14, 1929, in Chicago, marked a violent turning point in the city's organized crime history. The brutal slaying of seven members of the North Side Gang by gunmen allegedly linked to the South Side Italian mob exemplified the intense gangland rivalries and law enforcement's struggles to control rampant crime during the Prohibition era.

Key takeaways

  • The St. Valentine's Day Massacre: where organized crime's bloody ballet met law enforcement's 'oops, not again' moment.
  • Prohibition didn't just ban booze; it poured gasoline on the mob's turf wars—cheers to unintended consequences!
  • Capone’s rise reminds us: in the great American dream, some chase prosperity, others chase bodies.
  • Gangster uniforms: flashy suits and a license to kill—proof that style can indeed be deadly.
  • When seven gangsters drop in a single day, it's not just murder; it’s a clarion call to chaos.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Chicago, SMC Cartage Company, The St. Valentine's Day Massacre, Great Lakes
  2. – 10:00: Al Capone, Coney Island, Chicago, Brooklyn
  3. – 15:00: Chicago, Frankie Yale, Al Capone, Brooklyn
  4. – 20:00: Chicago, Al Capone, Johnny Torio, Brooklyn
  5. – 25:00: Chicago, Al Capone, Dean Oanion
  6. – 30:00: Chicago, Haimey Weiss, Al Capone, George Bugs Moran
  7. – 35:00: Chicago, Al Capone, Thompson submachine gun, Haimey Weiss
  8. – 39:09: Chicago, Al Capone, George Bugs Moran, The St. Valentine's Day Massacre

Notable quotes from "St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers"

  • You hop down from the truck and land directly in a pile of dirty snow. As icy water seeps into your shoe, you look over at the garage. There's no obvious sign that anything's a miss.
    about SMC Cartage Company · at
  • Time a densely populated and expanding urban area and became the epicenter of the bootlegging industry. Due to its location along the Great Lakes, Chicago was an ideal place…
    about Chicago · at
  • Opportunities to make more money than Capone had ever dreamed of. And by the end of his first year in Chicago, Capone vowed that he wasn't going to remain a glorified…
    about Al Capone · at
  • Coordinated who would buy which distilleries and who would pay off which politicians. Toriel believed that keeping everyone working together was better for business than letting 12 separate gangs compete for territory.
    about Johnny Torio · at
  • Business that competition increased and it was becoming evident that the peace couldn't hold forever. The most persistent thorn in Toriel's side was an Irish gang leader named Dean Oanion.
    about Dean Oanion · at
  • Oban's death left his close friend and top lieutenant, Haimey Weiss, in charge of the North Sight gang. Although Oan's murder was never officially solved, Weiss had no doubt about who was.
    about Haimey Weiss · at
  • Instead, he holed up at the Hawthorne Hotel in Cicero. And taking no chances, he installed bulletproof shutters on the windows and hired armed guards to patrol the lobby. Meanwhile, across the city,.
    about Hawthorne Hotel · at
  • The effect was so intimidating that soon every gangster in Chicago wanted a Tommy gun of their own. When Capone managed to procure one in the spring of 1926, his men promptly…
    about Thompson submachine gun · at

Who and what is mentioned in this episode?

People

  • Al Capone — Person · Primary historical subject · 15 mentions · first at
    Central figure whose rise in Chicago’s bootlegging underworld and conflict with the North Side Gang frames the lead-up to the St. Valentine’s Day Massacre.
  • Johnny Torio — Person · Referenced historical figure; Capone’s mentor/boss · 3 mentions · first at
    Depicted as the strategic leader who built a multi-gang syndicate (“the Outfit”), brought Capone to Chicago, and whose retirement enabled Capone’s takeover.
  • Haimey Weiss — Person · Referenced historical rival; successor North Side leader · 5 mentions · first at
    Takes over after O’Banion’s death and leads major retaliatory attacks against Torrio and Capone, including the Hawthorne Hotel shooting.
  • George Bugs Moran — Person · Referenced historical rival; North Side lieutenant/leader · 3 mentions · first at
    Identified as Weiss’s top lieutenant and later the remaining key North Side figure by early 1929—implied target leading into the massacre narrative.
    Shopping trip. Suddenly, a black Cadillac pulled up and Haimey Weiss and one of his top lieutenants, George Bugs Moran, jumped out of the car, pistols blazing. They shot Toriel…
  • Dean Oanion — Person · Referenced historical rival; North Side Gang leader · 2 mentions · first at
    Introduced as Capone/Torrio’s principal North Side rival whose repeated violations and betrayal escalated the gang war; his murder triggers retaliation cycles.
  • Frankie Yale — Person · Referenced historical enforcer/lieutenant · 4 mentions · first at
    Portrayed as Torrio’s top New York lieutenant who kills Colosimo and participates in O’Banion’s assassination; also helps move Capone to Chicago for safety.
    Jeopardize it. But unwilling to take no for an answer, in May 1920, Toriel summoned his top lieutenant Frankie Yale to pay Collimo a visit. Yale took a train from New York…
  • Lindsey Graham — Person · Host · 1 mention · first at
    Narrator/host introducing the series and guiding the historical storytelling framing of the massacre and Capone’s rise.
    From Wondery. I'm Lindsey Graham and this is American History Tellers. Our history, your story.
  • William Mcwigan — Person · Referenced victim; assistant state attorney · 1 mention · first at
    His death in a gang shooting triggers public outrage and intensified law enforcement pressure on Capone, shaping the crackdown context.
    Questions about what Mcwigan was doing in a car full of bootleggers, authorities highlighted the fact that Mcwigan had once bragged that he was going to put Al Capone away. A…
  • Terresa Capone — Person · Referenced family member (mother; transcript variant) · 1 mention · first at
    Mentioned alongside Gabriella in Capone’s origin story; the transcript appears to conflate/variant-spell Capone’s parents’ names.
    Naples, Italy 4 years earlier. Gabriella worked as a barber while Terresa brought in sewing. The couple also took in borders for extra income. But despite this, money was…
  • Gabriella Capone — Person · Referenced family member (mother) · 1 mention · first at
    Provides biographical grounding for Capone’s early life and immigrant family background; mentioned as a parent shaping his upbringing.
    Capone. The two had immigrated to America from a small town outside Naples, Italy 4 years earlier. Gabriella worked as a barber while Terresa brought in sewing. The couple also…

Books & papers

  • The St. Valentine's Day Massacre — Book · Primary recommendation · 3 mentions · first at
    Recommended reading for listeners interested in the St. Valentine's Day Massacre and its impact on organized crime.
    We recommend Al Capone, the Life, Legacy, and Legend by Dear Jar, The St. Valentine's Day Massacre by William J. Helmer, and Arthur J. Bilick, and Murder and Mayhem on Chicago's North Side by Troy Taylor.
  • Murder and Mayhem on Chicago's North Side — Book · Primary recommendation · 2 mentions
    Recommended reading for listeners interested in the violent history of Chicago's North Side gangs.
  • Al Capone, the Life, Legacy, and Legend — Book · Primary recommendation · 1 mention · first at
    Recommended reading for listeners interested in learning more about Al Capone and the Chicago Gang Wars.
    If you'd like to learn more about Al Capone and the Chicago Gang Wars, we recommend Al Capone, the Life, Legacy, and Legend by Dear Jar, The St. Valentine's Day Massacre by.

Companies & orgs

  • SMC Cartage Company — Company · Setting · 1 mention · first at
    Location of the St. Valentine's Day Massacre, where seven gang members were executed.

Products & tech

  • Thompson submachine gun — Product · Key weapon · 2 mentions · first at
    A revolutionary firearm that changed the nature of gang violence in Chicago, used extensively by gangs including Al Capone's outfit.

Places & events

  • Chicago — Place · Setting · 33 mentions · first at
    Primary location where the events of the episode take place, central to the narrative of the St. Valentine's Day Massacre and Al Capone's operations.
  • Hawthorne Hotel — Place · Headquarters · 2 mentions · first at
    Al Capone's base of operations in Cicero, where he conducted much of his business and survived an assassination attempt.
  • Brooklyn — Place · Setting · 5 mentions · first at
    Birthplace of Al Capone and initial setting for his early criminal activities before moving to Chicago.
    Came to town and quickly developed a bold vision for how to make as much money as possible. Born Alons Capone in 1899 in Brooklyn, New York, Al was the fourth child of…
  • Coney Island — Place · Setting · 3 mentions · first at
    Location in Brooklyn where Al Capone spent time and where key events in his early life took place.
    For his boys to get ahead. But one by one, Al's older brothers all dropped out of school. The eldest went to work in the horse stables on Coney Island, while the other two…
  • Great Lakes — Place · Setting · 1 mention · first at
    Geographical feature that made Chicago an ideal location for bootlegging operations due to its proximity to Canada.
    Time a densely populated and expanding urban area and became the epicenter of the bootlegging industry. Due to its location along the Great Lakes, Chicago was an ideal place…

Full transcript with timestamps

Wonder. Imagine it's late in the morning on February 14th, 1929. You're an officer in the Chicago Police Department and you're sitting in the passenger seat of a telephone repair truck as it drives down a snowy street of the north side neighborhood. You shouldn't need to hitch rides like this, but both of the station's patrol cars were in use when an urgent call came in about half an hour ago. So, you had to ask a workman who was repairing a phone at the station to drive you over. The repairman pulls in front of a brick building with the name SMC Cartage Company painted across a blacked out window.

You hop down from the truck and land directly in a pile of dirty snow. As icy water seeps into your shoe, you look over at the garage. There's no obvious sign that anything's a miss. But just then, one of the station's patrol cars screeches to a stop nearby. A beat cop jumps out. Hey, good timing. I heard the call on the radio to report here, but then the reception cut out. What's going on? Some lady called the station hysterical. Insisted that the garage was full of death and destruction. The sergeant said she sounded nutso, so it's probably nothing.

I bet she heard some car backfiring and assumed it was gunshots. Happens all the time. You and the other officer approached the door of the garage. He shoves his hands into his pockets. So, you got any plans tonight? You mean for Valentine's Day? No, I'm a bachelor, remember? Hey, hold on. You hear that? You bring your finger to your lips to tell your buddy to stay quiet. A surge of adrenaline runs through your chest. You unholster your gun and push through the open door, squinting into the dark. You immediately flinch as you're hit by the acidic coppery smell of fresh blood. The only light in the garage comes from a dim bulb hanging from the ceiling. A few feet away, you see a man lying on the ground, a revolver next to him. He doesn't appear to be breathing. A patrol officer next to you gags. Oh, Lord have mercy. You follow his gaze to the back of the garage where you see a slew of bodies.

You count six in total, wearing the kind of flashy suits that gangsters like to sport. Looks like this has to have been at pretty close range. Whoever shot them must have been just a few feet away. I thought I'd seen it all, but not carnage like this. Whoever did this is a monster. All right, come on. We got to call the station. We need to secure the scene and get more officers here. As you charge back into the icy air outside, your mind races. Since prohibition started 9 years ago, mobsters have been bootlegging alcohol in the city, and turf wars have exploded. So far, you've been content to let these criminals fight amongst themselves. But what you've just witnessed in that garage is beyond brutal. It's clear to you now that things have gone too far, and these gangsters need to be stopped.

from Wondery. I'm Lindsey Graham and this is American History Tellers. Our history, your story. On our show, we'll take you to the events, the times, and the people that shaped America and Americans, our values, our struggles, and our dreams. We'll put you in the shoes of everyday people as history was being made. And we'll show you how the events of the times affected them, their families, and affects you now. In January 1919, the United States ratified the 18th Amendment, banning the manufacturer and sale of alcohol across the country. When the law went into effect one year later, criminals rushed in to fill the demand with illicit booze. Chicago was at the time a densely populated and expanding urban area and became the epicenter of the bootlegging industry. Due to its location along the Great Lakes, Chicago was an ideal place for criminal gangs to make big money importing alcohol from

Canada. But with vast fortunes to be made, turf wars soon broke out. The city's murder rates skyrocketed as waring gangs participated in a vicious cycle of attacking and retaliating against each other. This violence reached its peak on February 14th, 1929 when seven gang members were shot at close range in what appeared to be an execution style murder. This unprecedented carnage shocked local law enforcement and outraged the public. And what became known as the St. Valentine's Day Massacre changed the face of organized crime in America and marked the beginning of the end for one of the country's most notorious criminals, Al Capone. This is episode one in our two-part series on the St. Valentine's Day Massacre, the land of milk and money.

In the early 1920s, a new kind of gangster set up shop in Chicago. After years of working as an enforcer and running brothel in New York, Al Capone came to town and quickly developed a bold vision for how to make as much money as possible. Born Alons Capone in 1899 in Brooklyn, New York, Al was the fourth child of Gabriella and Terresa Capone. The two had immigrated to America from a small town outside Naples, Italy 4 years earlier. Gabriella worked as a barber while Terresa brought in sewing. The couple also took in borders for extra income. But despite this, money was tight, especially as their family expanded to include eight children. Al's father, Gabriella, believed strongly in the American dream and thought that education was the way for his boys to get ahead. But one by one, Al's older brothers all dropped out of school. The eldest went to work in the horse stables on Coney Island, while

the other two brothers joined up with local street gangs, earning money running numbers and doing other errands for the gang bosses. For a while, Gabriella thought Al, who was a good student and a quick learner, especially in mathematics, would be the only one to graduate high school. But as a young man, Al had little patience and resented authority. Ultimately, he much preferred to hang out on the streets rather than a classroom. And by the time he was 8 years old, Al had already developed a reputation as a brawler. When he was 10, his favorite pastime was to hang out by the Navyyard and taunt the sailors, throwing rocks and bottles at them. He was big for his age and had no fear of provoking the eyeire of men twice as old as him. Then in 1913 when Al was in sixth grade, he got into an altercation with a teacher and decided he was done with school. He walked out and never returned. Instead, he started working in

the neighborhood. He held a variety of jobs, including working behind the counter at a candy store, setting pins in a bowling alley and shining shoes. He often brought his wages home to help his parents support his younger siblings. But Al soon figured out that there were ways to supplement his legitimate income. While shining shoes, he watched as enforcers from a local gang collected protection money from the various merchants, charging them a fee just to be able to operate safely. This gave Al the idea to start his own protection racket. It wasn't long before he roped in a couple of cousins and friends and sent them out to collect money from the other shoe shine boys. His plan was to keep his operation small enough that it would escape the notice of the more established gang in the neighborhood.

But they quickly caught on and kicked Al off their street, shutting down his scheme. But the endeavor gave Al a taste of another way to make money, and he soon joined up with his older brother, Frank, who was by then working odd jobs for a local gang boss named Johnny Toriel. One day, Toriel asked Al to meet him at an Italian social club Torio owned in lower Manhattan. When Al arrived, he was brought into Toriel's office and told to wait that Toriel would be with him in just a minute. Taking a look around, Al not noticed a large bag of money sitting on the desk.

Being a quick study, Al realized this was a test. So instead of walking over and pocketing a handful of bills, he sat there and waited, never touching the cash. Impressed with Al's integrity, Toriel brought him on as an errand boy for his gang. And as part of his new responsibilities, Al made the rounds at the gambling saloons Toriel operated, collecting the gang share of the previous night's earnings. His intimidating stature and predelection for violence made him an effective collector. He wasn't afraid to bash heads if someone failed to pay, and he even went so far as to practicing his menacing stare in the mirror. As time went on, he began collecting the so-called take from more and more of Toriel's establishments, including from brothel and bars, giving him the opportunity to learn how each business operated. Torio quickly recognized the young Capone's facility with numbers, and frequently assigned him to help

tally up the day's collections. Over the next several years, Capone continued to work his way up Toriel's operation, all while still holding down a variety of legitimate jobs. Then in 1917 when Capone was 18 years old, he met a young Irish woman named May Coughlin at a box factory where he was employed as a laborer. May worked as a timekeeper in the factory office and the two were instantly attracted to each other. Only a few months after they met, May was pregnant and the two were married in December 1918, a few weeks after their son was born. Newly married and with a young son, Capone tried to go on the straight and narrow. His wife May and their baby son lived with her parents in New York while Capone moved to Baltimore where he took up work as a bookkeeper for a construction company. He was considered a good and reliable worker, arriving on time every day in a clean suit and tie. But in November 1919, less

than a year after his son was born, Capone's father died of a heart attack at age 55. Capone's mother was bereff and his four younger siblings were still living at home. So Capone rushed back to New York. It was clear that none of his older brothers were up to the task of supporting their mother and other siblings. His oldest brother, James, had left to try to be a star in Hollywood, and no one had heard from him in years. His other two brothers were in complicated entanglements with women and had unreliable income. So, Capone decided to move back to Brooklyn for good. In truth, it was just the excuse he needed because he missed New York and hated being away from his family. But he knew that to support his wife, son, mother, and four younger siblings, he would need to make a lot of money and fast. So he went back to work for Johnny Toriel's outfit, collecting and enforcing. But things had changed in

Toriel's operation while Capone was away. Johnny Torio had been spending more and more time in Chicago, where his cousin's husband, known as Big Jim Collasimo, ran a string of brothel. Kazimo brought Torio out to be his right-hand man. But Torio had bigger ambitions than playing second fiddle, and a new opportunity was brewing in the underworld of America. For years, temperance advocates in the United States had been pushing to amend the Constitution to outlaw the sale of alcohol. And in 1919, they succeeded when the 18th Amendment was ratified to ban the manufacturing, sale, or transport of alcohol across the country.

Prohibition was set to begin on January 1st, 1920. But Torio knew that people's appetite for alcohol wasn't going to disappear just because it was illegal. He believed that rather than driving people to stop drinking, prohibition would create a massive black market. And he saw a chance to capitalize on it, and Chicago was the perfect place to set up shop. Thanks to German and Irish immigrants, the city had plenty of distilleries, and it had developed a strong drinking culture. It was also a major transportation hub and allowed easy access to Canada to smuggle liquor in from the north. But if that wasn't enough, there was already largescale political corruption, meaning it would be easy to pay authorities to look the other way. But when Toriel brought this idea to Colossimo, the brothel owner wasn't interested. He had a racket that worked for him and didn't want to jeopardize it. But unwilling to take no

for an answer, in May 1920, Toriel summoned his top lieutenant Frankie Yale to pay Collimo a visit. Yale took a train from New York, then walked into the Chicago restaurant that Collasimo operated from and shot him in broad daylight. Then Yale hopped back on the train. With Big Jim Collaso out of the way, Toriel took over his business and quickly expanded into bootlegging. Back in Brooklyn, Al Capone reported to Frankie Yale, who had come to appreciate Capone's willingness to do whatever was necessary, even murder, to get what was owed. And under Capone's watch, everyone from the brothel workers to the saloon employees stayed in line. But soon after Colosimo's death in Chicago, Capone found himself in hot water in New York.

A member of the Whiteanders, an Irish gang, had made a smart remark, disparaging Irish women who married Italian men. Capone took it as a personal insult since his wife May was Irish and he was Italian. So he beat the man until he was close to death. As a result, a higher up in the Whiteanders gang swore revenge on Capone. Frankie Yale knew this was no idol threat. He believed Capone, who he considered to be one of his most valuable assets, was in serious danger. So, he came up with a plan for how to protect his prized enforcer. But first, he had to convince Capone to go along with it.

Imagine it's a warm spring day in Coney Island, New York in 1920. You're sitting in your office in the Harbor Inn, a bar you own, listening to the seagull squawking outside. You're just finishing your tally of the previous night's take, and there's a knock on the door. Ah, come in. Al Capone enters the office. He's tall with a round face and two scars slashed across his cheek, the result of a bar fight in this very establishment. The young man's willingness to take on a bloody fight is one of the reasons he's such an asset.

But there are some downsides, too. Capone takes off his hat. You wanted to see me, boss? Yeah, have a seat. What's going on? Well, Wild Bill Love It has really been out of shape that you put a white-hander in the hospital. He's promising to kill you on site. Well, I'd like to see him try. No, no, you wouldn't. That man was a sharpshooter in the Great War. You even won a medal for it. Not to mention, he's crazier than Aloon. If he says he's going to kill you, he's going to kill you. Oh, don't worry, boss. I'm not a sharpshooter or anything, but you know I'm not a bad shot myself. I'll be sure to keep my head on a swivel. That's not going to be enough. As long as you're in New York, he's not going to stop coming after you, and we can't risk losing you. What are you suggesting? Well, Johnny could use some of your skills in Chicago, so maybe it's time for a change of scenery.

Capone runs his hand over his scarred cheek and shifts in his seat. Well, with all due respect to you and Johnny, Brooklyn's my home. My mother lives here, my siblings. I can't let some Irish punk chase me out of town just cuz he's running his mouth. You're not letting some Irish punk run you out. You're going where your boss Johnny Toriel is asking you to go for the good of the organization. You lean forward in your seat and look Capone dead in the eyes. And if you can't do what your boss is asking you to do, then there may no longer be a place for you within this operation. You understand what I'm saying? Capone gives a small nod. All right. Anyway, I hear Chicago is beautiful. You slide three train tickets across your desk. Now there's a good boy. Now go home and get your wife and son. Train leaves tonight.

Capone tucks the tickets into his inside coat pocket and nods again before walking out. You'll miss Al Capone's talents in Brooklyn, but you have a feeling he's going to do very well in Chicago. When Al Capone arrived in Chicago, his boss, Johnny Torio, immediately put him in charge of the brothel he'd taken over after Big Jim Colosimo's death. Capone kept things running smoothly, collecting the earnings, managing the books, and making sure the customers stayed in line. And as he got to know Chicago better, Capone began to understand what Toriel saw in the city. It hadn't earned the nickname the land of bil and money for nothing. Local politicians and law enforcement officers were all on the take. You could cater to the public's every whim, legal or not, with little interference. This offered opportunities to make more money than Capone had ever dreamed of. And by the end of his first year in Chicago, Capone

vowed that he wasn't going to remain a glorified babysitter of prostitutes forever. He intended to convince Johnny Toriel that with a little ingenuity, they could be running the whole city. And he was willing to do whatever it took to realize that dream.

By 1921, roughly a year after Al Capone had moved to Chicago, he had worked his way up to a prominent position in one of the most powerful organized crime groups in the city run by Johnny Toriel. Capone was now Toriel's chief lieutenant in a gang that Toriel called the Outfit. So instead of just managing brothel, Capone was now running Toriel's premier establishment, a multi-story building that housed a brothel, a nightclub, and a gambling hall known as Four Deuces because of its address, 2222 South Wabash Avenue. But Capone was not just a brawn. The time he'd spent as a bookkeeper in Baltimore was also paying off. His mathematical prowess came in handy as he managed the Chicago gangs accounts and developed creative ways to hide their income from tax collectors and law enforcement. His boss, Johnny Torio, was busy, too. Over time, he'd proven an effective leader, ultimately managing to unite approximately 12

neighborhood gangs, forming a cohesive syndicate. He divided territory and coordinated who would buy which distilleries and who would pay off which politicians. Toriel believed that keeping everyone working together was better for business than letting 12 separate gangs compete for territory. And for the first few years of prohibition, Toriel's plan worked well. The various Chicago gangs he oversaw were peaceful and worked in harmony. In the early 1920s, the crime rate actually dropped in Chicago, especially property related crimes. This was because bootlegging was safer and more lucrative than robbery or burglary. So career criminals went to work instead as drivers, distillers or collectors for bootleggers like Toriel. And there was so much money floating around that for the time being the various gang leaders were content to stay on their established turf. But by 1923, so many people had entered into the bootlegging

business that competition increased and it was becoming evident that the peace couldn't hold forever. The most persistent thorn in Toriel's side was an Irish gang leader named Dean Oanion. Born in a small town in central Illinois, Oanyan moved to the north side of Chicago when he was nine. Soon after, Oanion got involved with a local street gang called the Little Helens, pickpockets, and petty thieves. As he got older, he joined another gang, the Market Street Boys, who were employed by the Chicago Tribune to beat any news owner who didn't carry the paper. But eventually, Oion fell in with a more accomplished criminal who taught him how to crack safes. By the time Prohibition started in 1920, Obanyion was the leader of a group known as the North Side Gang.

And like Toriel, Oanion saw the potential gold mine Prohibition promised. He quickly bought up the best distilleries on the north side and established a trade route with Canada. While other bootleggers, including Toriel, were mostly selling dressed up moonshine. Oan earned a reputation for having the best quality alcohol in Chicago. He also had the right to distribute his alcohol on the north side, hence the name of his gang. While Toriel took control of the southside, including the neighboring city of Cicero. Oion was content to honor this agreement at first, but after a few years, his ambitions grew. So, in violation of his agreement with Toriel, Oanion started selling some of his alcohol to high-end establishments on the south side of the city. Their customers wanted better quality alcohol than what Toriel was providing, and Banyan didn't see why he shouldn't oblige them. The logic may have been

sound, but Oan's flouting of their agreement challenged Toriel's authority, and that was something Toriel could not let slide. Imagine it's spring 1923 on the south side of Chicago. You're sitting in a cold warehouse surrounded by barrels of bootleg beer. You're the boss of one of the biggest gangs in the city, but lately you feel like you haven't been getting the respect you deserve. So, you call a meeting with your top lieutenant, Al Capone, to figure out your next move. Capone saunders into the warehouse, a cigar dangling from his lips. He looks relaxed, but you can tell from the flash of anger in his eyes that he's chomping at the bit to take action against your north side rival. Johnny, just give me the word and I'll take out that Irish jerk myself. You shake your head. Capone is always quick to turn to violence as a solution. And what happens if we do that? I tell you what happens. They send

someone after us. Then we send someone after them and so on and so forth. And you know what happens in the meantime? Yeah, these north side thugs learn we're not to be messed with. Yeah, maybe. But we get police breathing down our necks. We lose some valuable workers. We're distracted by watching our backs. And overall, we make less money. So, no, no violence. There's another way to deal with Oan. Yeah. And what would that be? Look at it this way, and I hate to admit it, but he does have better product than us. And I understand why certain high-end places want his alcohol, so maybe we let him have that. Boss, hey, I'm not done. I'm sorry, Johnny. Please continue. So, we let them have that in exchange for access to warehouses on the north side. Oh, boss, you're a master dealmaker. No doubt about it. But I'm telling you, there's no reasoning with guys like Oanion. And much as some warehouses up there would help our

operation, I just don't think Oanian's word means much. He agreed to only distribute north of Madison. And then without permission, he started distributing in our territory. What makes you think he'll honor this new agreement? Well, I don't believe he's an unreasonable man. We'll just have to explain it to him in a way he'll understand. I'm telling you, Johnny Oion won't listen. He thinks we're a bunch of heathen grease balls. Well, it's your job to make him see reason. And I'm saying there's only one way to do that.

No, Al, you listen up. War, it's bad for business. The longer we can keep the peace, the better. I'm trusting you to take care of this and take care of it the right way. Capone takes a long drag on his cigar and blows a smoke ring into the air. You're the boss, boss. Capone strides out, leaving you alone in the warehouse. You adamantly believe that maintaining peace is key, but you hope that you're right that Oanion can be brought into line without resorting to violence. Otherwise, things could get real nasty in Chicago.

In late 1923, Al Capone approached North Side gang leader Dean Oanion with a proposal. Capone and Toriel would be allowed to operate warehouses in the north side in exchange for letting Obanyion distribute alcohol to certain restaurants on the south side, but Oanion rejected the idea. Still, Toriel continued to try to find a way to compromise with Oanion. There were over a dozen meetings between the two organizations, and over and over, Oanion agreed to respect the terms of their agreement and then went right back to violating them. And as time went on, his transgressions grew even bolder. Not only did he distribute Enoro's territory, he started hijacking Toriel's trucks and robbing his distilleries.

Capone repeatedly called for violent retaliation. But Toriel remained committed to keeping the peace until finally Oanion went too far. In May 1924, Oanion approached Toriel and told him he was getting out of the business. He offered to sell Toriel some of his establishments, including a brewery on the north side. Toriel agreed and paid Oanyan a half million in cash. On May 19th, 1924, Toriel arrived at the brewery to inspect his new property. But just a few minutes after he arrived, 20 police officers raided the building, arresting everyone inside, including Toriel. Toriel immediately realized Oan had set him up. He had never intended to retire. It was all a ruse. This was Toriel's second arrest for violating prohibition. The first time he'd been ordered to pay a fine, but he knew this second offense would mean jail time.

Rubbing salt in the wound, Oanion paid the bail for everyone arrested except for Toriel. Paying his own bail, Toriel was furious. He finally realized that Capone was right. The only way to deal with Oan was to kill him regardless of the consequences. So, 6 months later, in November 1924, three men, including Toriel's right-hand man from New York, Frankie Yale, walked into a flower store that Oan operated as a front. They said they were there to pick up a funeral wreath that had been ordered earlier in the day. When Oanyan came out from around the counter to give them the wreath, Yale shook his hand and then clamped down hard. He yanked Obanyion toward him and shoved his pistol into Oban's stomach. The two other men moved to either side and all three opened fire. Oban was shot in the chest, throat, and face. He fell into a display of geraniums, and the three gunmen fled, jumping into the car, idling out front.

Oban's death left his close friend and top lieutenant, Haimey Weiss, in charge of the North Sight gang. Although Oan's murder was never officially solved, Weiss had no doubt about who was responsible and swore revenge against Toriel. It didn't take long for Weiss to act. On January 12th, 1925, Toriel and his wife were exiting their limousine outside their house on the south side of Chicago. They had just returned from a shopping trip. Suddenly, a black Cadillac pulled up and Haimey Weiss and one of his top lieutenants, George Bugs Moran, jumped out of the car, pistols blazing. They shot Toriel five times, hitting him in the groin, chest, neck, and arm before returning to their car and speeding away. Miraculously, Toriel survived the attack. He spent a month in the hospital, and Capone made sure Toriel's room was guarded at all times.

He personally slept on a cot by Toriel's bed every night and made sure his guns were fully visible. The hospital staff was too scared to say anything. But that wasn't the end of bad luck for Toriel. When he was released from the hospital, he was due in court for the brewery raid. There, he was sentenced to serve 9 months in prison. While he did this time, Toriel turned over the Chicago outfit to Capone to run. And by paying off guards and wardens, Toriel was able to ride out his prison sentence in relative comfort. He brought in his own furniture and was able to eat dinner every night at the sheriff's house nearby. He even entertained guests there. And during this mandatory break from gang life, he came to the decision that it was time to retire. When Toriel was released from prison near the end of 1925, Capone was there to meet him.

Toriel was still worried about threats on his life, so Capone arranged for an armored limousine to transport Toriel and his wife to a train station in Indiana. There, Capone paid armed men to patrol the platform until the train departed for Florida, where Toriel and his wife would set sail for an Italian vacation. Later, they settled in Westchester outside New York City. That left the outfit the gang Torielo had tirelessly put together for years now in the hands of Al Capone and he was just 25 years old. But the carefully calibrated orchestra of gangsters that Toriel had assembled was fracturing. By the end of 1925, Toriel's smoothly operating syndicate had dissolved. Rival gangs were back to battling each other for bigger pieces of the pie. Capone found himself fighting just to maintain control of the territory he'd inherited. And he knew it would take all his wits, savvy, and cold-blooded instincts to

maintain his position at the top. In 1925, when Al Capone took over the outfit, he found himself at the head of a sophisticated corporation with diverse revenue streams. The gang operated hundreds of speak easys, brothel, gambling dens, and roadouses throughout Chicago. This sprawling criminal syndicate was bringing in up to 100 million a year, equivalent to 1.5 billion today, and employed over 1,000 people. As leader, Capone faced the same types of problems that troubled the heads of any massive organization. There were distributors who bungled deliveries, employees who griped about compensation, and retailers who failed to pay what they owed. But beyond all those problems, Capone also had to worry about his personal safety. The North Side gang, now run by Haimey Weiss, still had its eye on the outfit's territory, and they had aligned themselves with a Westside gang who was making moves into the outfit stronghold

in Cicero. Fearing attempts on his life, Capone spent almost no time in his family home in the suburbs of Chicago. Instead, he holed up at the Hawthorne Hotel in Cicero. And taking no chances, he installed bulletproof shutters on the windows and hired armed guards to patrol the lobby. Meanwhile, across the city, smaller gangs continued to war with each other. They hijacked trucks, robbed distilleries, and mowed down their rivals in shootings. Adding to the chaos, a powerful new weapon had arrived on the scene, changing the tenor of the fighting. Just before he died in 1924, Dean Oan had taken a trip to Colorado.

There he encountered a new type of firearm, the Thompson submachine gun, or Tommy gun for short. This was a handheld automatic machine gun that spewed out a torrent of bullets. At the time, most automatic weapons weighed over 50 lbs and needed two or three people to maneuver. They were weapons of war with little use on the streets. So, the idea of a lightweight automatic weapon that was smaller than a rifle seemed too good to be true. Oion bought three and brought them back to Chicago. And after Oan's death, the Northsiders put these powerful new weapons to use in their various assassination attempts. Their normal tactic was to drive by a rival gang's establishment and a gunman would lean out of the car window, raining dozens of bullets down on the building.

The effect was so intimidating that soon every gangster in Chicago wanted a Tommy gun of their own. When Capone managed to procure one in the spring of 1926, his men promptly unloaded 92 bullets into a beauty shop in an attempt to kill a rival Westside gangster who was there visiting his girlfriend. And other gangsters soon got their hands on the technologically superior weapon. The result was that by the end of 1926, there had been 75 gangland killings, a sharp increase from the year before. But despite this market increase in murders, for the most part, the public was inure to the gang violence. Many wrote it off as gangsters killing gangsters, something that didn't concern them, and many residents were still more than happy to drink the booze that the gangsters were supplying. But one evening in April 1926, a car full of gangsters shot up a saloon called the Pony Inn in Cicero. The men shot through

the windows of a touring car and scattered bullets into the building itself. They also shot lead into a Lincoln that had just parked in front of the tavern. When the shooting stopped, four people were dead. Three of the victims were known bootleggers, but the fourth was a 27-year-old assistant state attorney named William Mwigan. The next day, the press blasted headlines that gangsters had murdered a prosecutor, and the public was outraged. Despite questions about what Mcwigan was doing in a car full of bootleggers, authorities highlighted the fact that Mcwigan had once bragged that he was going to put Al Capone away. A reporter even claimed that Capone had personally fired the bullet that killed the attorney, and it didn't take long for Capone to become the prime suspect, and police were convinced they were finally going to bring Al Capone down. Officers soon flooded Cicero, raiding Capone's

establishments there. They searched the residences of his known associates and tore apart his house, upsetting his wife and son. But what they didn't realize was that Capone had fled Chicago as soon as he had learned that charges had been filed against him. He hightailed it to Lancing, Michigan, where a trusted associate had a safe house. But despite going on the run, Capone had no intention of leaving his business in anyone else's hands. He continued to run the outfit from afar, setting up temporary headquarters in a hotel in downtown Lancing. And in the meantime, his men drove in from Chicago for frequent meetings to keep him up to date on what was happening back in the city.

But as time went on, Capone grew restless. So that summer, at a meeting with his men, Capone revealed that he'd made a decision. Imagine it's a hot, muggy day in July 1926. Your legs ache as you walk through the lobby of a hotel in downtown Lancing. You're a lieutenant in the outfit, and you've just driven over 200 miles to get here from Chicago. It's a drive you've gotten familiar with over the past few months, ever since your boss, Al Capone, decamped here. You make your way into a back room, find Capone digging into a steak. He gestures at a seat with his knife. Hey, sit. Sit. You want something to eat? Nah, I'm good. So, what's the damage this week? Well, we had three trucks hijacked, two distilleries robbed, but we'll make them pay.

Don't worry. That's fewer than a few weeks ago. It's true. Yeah. The Westside O'Donald's have lost most of their leaders. The Genna family's been picked off. I think the war is slowing down. And the police, they figure out a way to pin the state attorney thing on me. No. I talked to my guy in the department. They said nothing. Apparently, the brass is getting very frustrated. Capone puts down his fork, leans back in his chair. Well, then that makes it easy. I've decided it's time for me to come back home to Chicago. Hey, you sure? It's like you said, the police got nothing, right? It's been 3 months. The war's winding down. We won. Time to claim the spoils of victory, I say. Okay, boss.

But make no mistake, Haimey Weiss, Bugs, Moran, the other North Side boys, they still have it out for you. Oh, don't worry. I think we can reach an agreement. You raised your eyebrows. I thought that's how this all got kicked off. I mean, Toriel, all due respect, he thought he could make a deal with those no good Irish thugs. You blew up in his face. What makes you think they'll honor a deal now? Thousands of spent bullets, millions of dollars lost in property damage and stolen goods, dozens of dead friends. Well, I could go on, I guess.

Look, there are some people out there you can tell them the stove is hot and they won't touch it. They're smart like that. But others, they got to get burned before they believe it. The Northsiders had to touch the stove themselves, but now they know it's hot and we can burn him again. That's right. Now go back. Tell the guys at the Hawthorne that the boss is coming home. You nod and stand up to head back to your car. You won't miss the long drive to Lancing from Chicago, but the truth is Capone's return to the city makes you nervous. You're not sure the North Side gang has learned its lesson the way Capone says they have, but you keep your mouth shut and follow orders.

You know, Capone's not someone to second guessess. When Al Capone returned to Chicago in late July 1926, he turned himself in to the police. But once they had him in custody, they were forced to admit they had no evidence tying him to the murder of Assistant State Attorney William Mcwigan. A judge dropped all charges. Free from the spectre of arrest, Capone threw himself back into work. He returned to the Hawthorne Hotel and began talks with Haimey Weiss, leader of the Northside gang. He told Weiss he was tired of the violence and he wanted to end the war. Those talks were still ongoing when on September 20th, 1926, Capone was eating at a restaurant in the Hawthorne. Suddenly, a line of cars came rushing down the street, skidding to a stop in front of the hotel. Armed men emerged and unleashed a barrage of bullets. A bodyguard shoved Capone to the floor and he managed to crawl out through a back door. The gunmen emptied

cliff after cliff into the hotel. After a moment, Weiss and his top lieutenant, George Bugs Moran, jumped out of one of the cars and ran to the entryway of the hotel. Weiss waved his gun back and forth, firing into the lobby. Ultimately, the northsiders shot over a thousand bullets into the Hawthorne. Miraculously, no one was killed, but the shooting put an end to the peace talks. Al Capone was infuriated by the attempt on his life. He wasted no time in taking revenge. In early October 1926, Weiss was gunned down crossing the street in front of his headquarters on the north side. And over the next few years, almost every higher up in the north side gang was either killed or fled Chicago.

None of the murders could ever be pinned on Capone, but everyone assumed he was behind the hits. So by early 1929, only one top lieutenant in the north side gang was left, George Bugs Moran, there was little doubt there was a target on his back. But as Capone's war with the northsiders continued, the hits got more and more violent until even hardened Chicago residents began to think that gang leaders had gone too far. From Wondery, this is episode one of our two-part series on the St. Valentine's Day massacre for American history tellers. In the next episode, a gruesome shooting in a garage provokes local and federal government to finally take action to stop the bootleggers. And Al Capone finds himself facing threats from all sides as public sentiment turns against him.

If you'd like to learn more about Al Capone and the Chicago Gang Wars, we recommend Al Capone, the Life, Legacy, and Legend by Dear Jar, The St. Valentine's Day Massacre by William J. Helmer, and Arthur J. Bilick, and Murder and Mayhem on Chicago's North Side by Troy Taylor. American History Tellers is hosted, edited, and produced by me, Lindsey Graham, Airship. Audio editing by Muhammad Shazi. Sound design by Molly Bach. Music by Thrum. This episode is written by Austin Rackless, edited by Dorian Marina, managing producer Desi Bllelock, senior producers Alita Rosanski and Andy Beckerman. Executive producers are Jenny Lauer Beckman and Marshall Louie for Wondery.

Questions about this episode

Who speaks in "St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers"?

Lindsey Graham (Host), Al Capone (Guest), Johnny Torio (Guest), Dean O'Banion (Guest), Haimey Weiss (Guest).

What is "St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers" about?

The St. Valentine's Day Massacre, which took place on February 14, 1929, in Chicago, marked a violent turning point in the city's organized crime history. The brutal slaying of seven members of the North Side Gang by gunmen allegedly linked to the South Side Italian mob exemplified the intense gangland rivalries and law enforcement's struggles to control rampant crime during the Prohibition era.

What is mentioned in this American History Tellers episode?

20 people, works and ideas are mentioned, including Chicago, Al Capone, Johnny Torio, Haimey Weiss, George Bugs Moran, Dean Oanion. Each one on this page links to its own page with every episode that mentions it.

How long is "St. Valentines Day Massacre | The Land of Bilk and Money | American History Tellers"?

The episode runs 39 min; the transcript is about 6,948 words in 50 timestamped sections.

More from American History Tellers

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated February 15, 2026.