St. Valentines Day Massacre | The Land of Bilk and Money | 1

0:13Imagine 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.

0:53As icy water seeps into your shoe, you look over at the garage. There's no obvious sign that anything's amiss. 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 Sarge 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 approach the door of the garage.

1:29He shoves his hands into his pockets. So, you got any plans tonight? You mean for Valentine's Day? Nah, 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.

2:06The troll 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. Not carnage like this. Whoever did this is a monster. All right, come on, we've 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 nine years ago, mobsters have been bootlegging alcohol in the city, and turf wars have exploded.

2:53So 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.

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3:47From Wondery, I'm Lindsey Graham, and this is American History Tellers. Our history, your story.

4:09On 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 manufacture 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.

4:50Due 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 rate skyrocketed as warring gangs participated in a vicious cycle of attacking and retaliating against each other. This violence reached its peak on February 14, 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.

5:37This is episode one in our two-part series on the St. Valentine's Day Massacre, the land of bilk and money.

5:48In the early 1920s, a new kind of gangster set up shop in Chicago. After years of working as an enforcer and running brothels in New York, Al Capone came to town and quickly developed a bold vision for how to make as much money as possible. Born Alphonse Capone in 1899 in Brooklyn, New York, Al was the fourth child of Gabriela and Teresa Capone. The two had immigrated to America from a small town outside Naples, Italy four years earlier. Gabriela worked as a barber, while Teresa brought in sewing. The couple also took in boarders for extra income, but despite this, money was tight, especially as their family expanded to include eight children.

6:30Al's father, Gabriela, 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, Gabriela 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.

7:03Ultimately, he much preferred to hang out on the streets rather than a classroom. And by the time he was eight years old, Al had already developed a reputation as a brawler. When he was 10, his favorite pastime was to hang out by the Navy Yard and taunt the sailors, throwing rocks and bottles at them. He was big for his age and had no fear of provoking the ire 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.

7:43He 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 shoeshine 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.

8:23But 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 Torrio. One day, Torrio asked Al to meet him at an Italian social club Torrio owned in Lower Manhattan. When Al arrived, he was brought into Torrio's office and told to wait, that Torrio would be with him in just a minute. Taking a look around, Al 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.

9:00Impressed with Al's integrity, Torrio 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 Torrio operated, collecting the gang's share of the previous night's earnings. His intimidating stature and predilection 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 Torrio's establishments, including from brothels and bars, giving him the opportunity to learn how each business operated.

9:36Torrio 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 Torrio'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.

10:14Newly 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 bereft, 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.

10:52His 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 Torrio's outfit, collecting and enforcing. But things had changed in Torrio's operation while Capone was away.

11:29Johnny Torrio had been spending more and more time in Chicago, where his cousin's husband, known as Big Jim Colosimo, ran a string of brothels. Colosimo brought Torrio out to be his right-hand man, Vittorio 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 1, 1920.

12:05Vittorio 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 large-scale political corruption, meaning it would be easy to pay authorities to look the other way.

12:42But when Torrio brought this idea to Colosimo, 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, Torrio summoned his top lieutenant Frankie Yale to pay Colosimo a visit. Yale took a train from New York, then walked into the Chicago restaurant that Colosimo operated from and shot him in broad daylight. Then Yale hopped back on the train. With Big Jim Colosimo out of the way, Torrio 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.

13:24And 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 White Handers, 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, the higher up in the White Handers gang swore revenge on Capone. Frankie Yale knew this was no idle threat. He believed Capone, who he considered to be one of his most valuable assets, was in serious danger.

14:05So 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.

14:15Imagine it's a warm spring day in Coney Island, New York, in 1920. You're sitting in your office in the Harvard Inn, a bar you own, listening to the seagulls squawking outside. You're just finishing your tally of the previous night's take. There's a knock on the door. 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?

14:51Yeah, have a seat. What's going on? Well, while Bill Lovett had really been out of shape that you put a white-hander in the hospital, he's promising to kill you on sight. Well, I'd like to see him try. No, no, you wouldn't. That man was a sharpshooter in the Great War. He even won a medal for it. Not to mention he's crazier than a loon. If he says he's going to kill you, he's going to kill you. 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.

15:26And 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 because he's running his mouth. You're not letting some Irish punk run you out. You're going where your boss, Johnny Torrio, is asking you to go for the good of the organization. You lean forward in your seat and look Capone dead in the eyes.

16:00And 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's 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.

16:39When Al Capone arrived in Chicago, his boss Johnny Torrio immediately put him in charge of the brothels he'd taken over after Big Jim Colosomov'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 Torrio saw in the city. It hadn't earned the nickname the Land of Bilk 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.

17:16And 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 Torrio that with a little ingenuity, they could be running the whole city. He was willing to do whatever it took to realize that dream.

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19:42By 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 Torrio. Capone was now Torrio's chief lieutenant in a gang that Torrio called The Outfit. So instead of just managing brothels, Capone was now running Torrio'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.

20:20His mathematical prowess came in handy as he managed the Chicago gang's accounts and developed creative ways to hide their income from tax collectors and law enforcement. His boss, Johnny Torrio, 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. Torrio 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, Torrio's plan worked well.

20:58The 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 Torrio. 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, the competition increased, and it was becoming evident that the peace couldn't hold forever.

21:37The most persistent thorn in Torrio's side was an Irish gang leader named Dean O 'Banion. Born in a small town in central Illinois, O 'Banion moved to the north side of Chicago when he was nine. Soon after, O 'Banion got involved with a local street gang called the Little Hellions, 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 newsstand owner who didn't carry the paper. But eventually, O 'Banion fell in with a more accomplished criminal who taught him how to crack safes. By the time Prohibition started in 1920, O 'Banion was the leader of a group known as the Northside Gang, and like Torrio, O 'Banion saw the potential gold mine Prohibition promised.

22:20He quickly bought up the best distilleries on the Northside and established a trade route with Canada. While other bootleggers, including Torrio, were mostly selling dressed-up moonshine, O 'Banion 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 Torrio took control of the South Side, including the neighboring city of Cicero. O 'Banion was content to honor this agreement at first, but after a few years, his ambitions grew. So in violation of his agreement with Torrio, O 'Banion started selling some of his alcohol to high-end establishments on the south side of the city.

22:58Their customers wanted better quality alcohol than what Torrio was providing, and O 'Banion didn't see why he shouldn't oblige them. The logic may have been sound, but O 'Banion's flouting of their agreement challenged Torrio's authority, and that was something Torrio could not let slide.

23:18Imagine 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 the 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.