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near you. That's the letter K, the number 12 dot com slash HTDS. K12 dot com slash HTDS. It's a little past 1 a.m., Monday, March 22nd, 1920, roughly two months since the start of Prohibition. We're on the Washington state coast, about 20 miles north of Seattle, where a Lieutenant Roy Olmsted of the Seattle Police and a dozen or so others are waiting impatiently on Meadowdale Dock.
They haven't been here long, and they know that their intel is good. That any minute now, a rum runner, that is, a bootlegger ship or boat, will arrive with an obscene amount of Canadian whiskey. But still, standing in the cold dark morning grows tedious fast. Suddenly, they hear it, the distant sound of a humming motor. Now peering across the Puget Sound, the lieutenant sees the silhouette of a launch speeding across the moonlit waters and directly at his group.
Ah, most excellent. His contacts have come through. This bootlegging policeman couldn't be happier. That's right, Roy's a crooked cop. And since that launch still won't make it here for a few minutes, let me fill you in on how he turned bootlegger. Roy Olmsted has a lot going for him. He's well-built, charming, intelligent, numbering among Seattle's finest since 1906, this family man and friend of the mayor quickly ascended the ranks and gained influence.
He also took note of the rise in crime since Washington State instituted prohibition back in 1916. Roy watched as two rival gangs, one led by former policeman Jack Marquette, the other by a set of brothers, Fred and Logan, aka Slim Billingsley, left dead bodies on the streets of Seattle. He also watched gangsters make veritable fortunes and being far more intelligent than most, if not all of them. Well, Roy decided to get in on the action himself.
How long he's been at it now, I can't say, but we know that in these early months of national prohibition backed by federal enforcement, the 34-year-old bootlegging policeman is among those on the dock tonight. But enough about Roy. The launch is tying off on the dock. Time for us to move some booze.
The group gets to work, hefting case after case of Canadian whiskey from the speedboat across the dock and into a car parked just beyond on a narrow road near some tracks belonging to the Great Northern Railway. They work quickly, but not all that quietly. In fact, one man's voice cuts above all competing sounds of shuffling feet, sloshing liquor, and lapping water.
He seems to be directing foot traffic as bootleggers stream back and forth on the dock, but surely he must be disturbing some nearby neighbors. His flashlight too. The gentleman appears to give little thought as he casts its beam into the black morning, but the work continues. Once a car is loaded, a couple of bootleggers hop in and drive off as the next of their eight or nine cars pulls up. And so it goes, loudly, but systematically and smoothly.
At some unspecified point, Seattle police officer Roy Olmsted's car is loaded. He likely has a passenger, an unknown woman, but we can't say for sure. Be that as it may, Roy starts the car up, engages the clutch and begins ascending the steep and narrow road. Roy drives on, his automobile climbing the hill, but then he notices something in the distance, something in the road itself. Finally, it comes within the beams of his headlights.
It's a barricade, manned by federal and local station agents, with machine guns no less. Determined to protect his local celebrity policeman profile, Roy cranks the wheel and gasses it, driving hard into the nearby brush. As the bootlegging lawman makes this desperate attempt, the fed's machine gun glows in scenes spitting lead at him. The car is struck several times, and yet, Roy gets away. So does one other liquor-laden vehicle. As for the other half a dozen cars though,
They're stopped and apprehended. As the last of the cars are dealt with, station agent Norman Busfield moves down the hill and onto the beach. He sees that the rum runners are casting off their last line. "We'll have to move fast." Norman steps onto the dock, firing his rifle while advancing. The rum runners respond by desperately attempting to start their engine. It spits, sputters, and finally roars to life. The boat zips off into the dark morning and is soon lost from sight.
The feds have been waiting for days to make this bust, and it was worth it. They captured six cars, seized 96 cases and 10 quarts of Canadian whiskey, and apprehended nine men. Actually, 11 as the day drags on. For all his efforts to conceal himself, Roy Olmsted was recognized. They arrest him at home. The authorities also catch his fellow officer, Sergeant Thomas Clark, and the notorious Billingsley brothers.
And though the rum runners escaped, their speedboat now has an easily identifiable bullet-ridden hole. It's a real victory for law enforcement, even as they put away two of their own. But it's hardly a dent in the bootlegging game. Indeed, the fight to stop the flow of liquor into the United States is only beginning. Welcome to History That Doesn't Suck. I'm your professor, Greg Jackson, and I'd like to tell you a story.
Roy Olmsted gets fired from the force. He gets fined $500. All good by Roy. He now turns to bootlegging full-time. He amasses a fortune before a wiretap brings him down in 1925. Charged with violating the Volstead Act and conspiracy, the jury finds him guilty and Roy receives a four-year sentence and an $8,000 fine.
The former cop appeals, arguing his Fourth and Fifth Amendment rights were violated, but no such luck. In a 5-4 decision, the U.S. Supreme Court upholds Roy's conviction, setting a precedent that won't change again until Katz v. United States in 1967. So ends the criminal career of the King of the Puget Sound Bootleggers, or "The Good Bootlegger," as Roy was also known, because he refused to let his men carry weapons or take lives.
And today, in this second of three prohibition episodes, we'll see that Roy deserved to stand out for his nonviolent ways amid the violence and murder that comes with America's ban on booze. We'll start by digging into prohibition's enforcing law, the Volstead Act, which actually does allow some drinking. We'll explore that, then meet the law's defender, the prohibition agents.
We'll bust a speakeasy with famed prohibition agent Izzy Einstein, as well as a still operation in Montana with agent Ben Holter. Ah, but once we know the law and its enforcers, it's off to the underworld. And I'm not just talking about busting a club or a single rum runner. I'm talking high-level organized crime types. Now, there are more romanticized and deadly gangsters than we can ever meet in a few episodes, but we have an excellent sampling here.
First, the murderous tale of Cincinnati's early 1920s king of the bootleggers, George Remus. Second is New York's deadly and seemingly bulletproof Jack Legs Diamond. And then we go deep on New York, following the sordid story of Sicilian-born Charlie Lucky Luciano as this mafioso and his Jewish gangster buddies, Meyer Lansky and Benjamin Bugsy Siegel, redefine organized crime in The Big Apple.
So grab your trench coat and grab your gat. These streets aren't safe. And we begin by making sure we understand the laws we'll soon see broken with abandon, which means going back to the start of the year, just a few months before Roy got caught his first time and fired from the Seattle police force. Rewind. Most Americans are compliant as the alcohol-prohibiting 18th Amendment goes into effect on January 17th, 1920.
Some replace their old liquor habit with a new soda pop habit. They even keep drinking at the same place as saloons pivot from serving gin and tonic to just tonic. Others are slowly working their way through their home collection. Yes, the home collection is, as we learned in episode 157, perfectly legal.
While the 18th Amendment prohibits the manufacture, sale, or transportation of intoxicating liquors, it does not prohibit owning or consuming said intoxicating liquors. Nor does the amendment's far more detailed enforcer, the Volstead Act.
In fact, it expressly states otherwise in section 33, to quote the law, Close quote.
Naturally, the wealthy benefit from this loophole the most. They're the ones with the cash and storage space to secure ungodly stockpiles of their favorite inebriating libations before the booze-less bewitching hour strikes. One such example is Joseph Kennedy. Acting before January 1920, the future presidential father filled his Brookline, Massachusetts home with a wine collection that would make Bacchus red with envy.
And side note, later claims that Joseph makes a second fortune bootlegging are unsubstantiated and probably bogus. The origins of these rumors are likely due to him sharing a name with Canada-based liquor producer Joseph Kennedy, whose jazz and silk hat cocktails are incredibly popular. Anyhow, there are other exceptions in the Volstead Act.
We hit some of these in episode 157, but I'll remind you that priests and rabbis can still get wine, homemade cider is in the clear, and medical uses are still in play too. Unsurprisingly, doctors see a sizable uptick in patients seeking a prescription for whiskey or scotch to cure what ails them. That all said, let's not make too much of these small exceptions or loopholes.
The Anti-Saloon League's success in getting the Volstead Act to define anything above a 0.5% alcohol content as intoxicating is incredibly limiting, and even though most Americans are compliant, there are more than enough who aren't. In fact, so many are boozing illegally that the Boston Herald asks its readers to invent a new word to describe those who so brazenly break prohibition laws. 25,000 readers submit.
Two contestants end up splitting the $200 prize as they each come up with the same word, scoff law. And with so many Americans so willing to scoff at this law, that is, at prohibition, Uncle Sam needs someone to enforce it. That's where the Treasury Department's Bureau of Internal Revenue comes in.
Yeah, you heard that correctly. While the Coast Guard, Customs Bureau, J. Edgar Hoover's Bureau of Investigation, that is, the predecessor of the FBI, and of course, local law enforcement all play their part, the Prohibition buck stops with the Bureau of Internal Revenue. This bureau, later to be known as the Internal Revenue Service, or the IRS, soon establishes the Prohibition Unit, which consists of just more than 1,500 agents, all of whom are better armed than trained.
They're covering all 48 states. Yeah, they're spread thin. But don't discount them just yet. Some of these agents prove incredibly capable. Like Isidore, Izzy Einstein. A Jewish immigrant from Eastern Europe, Izzy speaks Yiddish, Hungarian, Polish, German. You know what? This could take a while. Let's just say he's a true polyglot. And that gift of tongues is part of what makes him so successful. One day, he poses as a German pickle packer.
The next, he's a Hungarian violinist or perhaps a Russian fisherman. Yes, despite his conspicuous appearance at 5'5" and 225 pounds, he's basically a shorter doppelganger to Alfred Hitchcock. Izzy is a master of disguise. He'll convince you that he's whoever you want him to be until it's too late. It's an unspecified day in early 1922.
A heavy set man in a boater hat and suit is lingering near the front door of the Yorkville Casino situated between 2nd and 3rd Avenue on 86th Street in New York City. The ornate six-story building of limestone, brick, and terracotta trim has served as home to a musician's union since the 1860s. And that's exactly the angle our lingering friend, Prohibition agent Izzy Einstein, is relying on to get in.
See, the musicians' union is above the casino, and you can't just waltz in. You need an invite, because this union has its own bar to serve the creative needs of its 1,000 or so musical members. And so, here's Izzy, down by the door, looking for someone to offer him an invite. Soon enough, a gentleman approaches the stout but friendly undercover agent. Where are you from?
Izzy plays his part. The Eastern European native answers in a perfectly American accent. "I'm a native of Pittsburgh, far from home and out of a job. Maybe I could get you one. What do you play?" "I play the trombone." That's good enough for this musician. He brings Izzy upstairs to the musicians' union. Stepping into the room, Izzy must be ecstatic.
No other agent has managed to get in here before, and now his eyes are drinking in the sight of taps, bottles, cocktails. This is clearly an illegal speakeasy. But as the heavyset agent absorbs his surroundings, his new friend comes back. Ever looking to be helpful, the man has a request for the allegedly out-of-work musician. Play something. Let's hear how good you are. Thinking quickly, Izzy tells the suspicious crowd that he left his bone at home. But that's fine.
They've got one for him to play. Izzy takes the trombone in his hands. He raises the mouthpiece to his lips. And wouldn't you know it, he begins to play. Of course, the multilingual, voice-shifting master of disguises actually plays. Why wouldn't he? Perhaps with a sense of irony, Izzy plays a piece called How Dry I Am. It works. The crowd is sold. They tell him to come back that evening, and they'll have a job for him. Well, Izzy will come back.
but with a warrant. The bartender's bane, the scourge of the speakeasies, the terror of the tenderloin. Whatever you call him, Izzy Einstein is a legend. He even has a catchphrase. As he slaps the cuffs on a suspect, he says, "'There's sad news here. "'You're under arrest.'"
During his years as a federal prohibition agent from 1920 to 1925, Izzy delivers that line thousands of times. 4,932 times, to be exact, if he really says it every time he and his partner, Moe Smith, make an arrest. The nation just eats up the tales of their exploits.
But while this famous duo is making headlines, most prohibition agents struggle just to cover their ground, especially near those thousands of miles long borders with more permissive Mexico and Canada. Alcohol is legal in Mexico, meaning these southern smugglers, or tequileros as they're known, in a nod to Mexico's famous agave-based liquor, run no risks until they reach U.S. soil.
Not that it's a big problem. There are only 24 federal prohibition agents assigned to the Mexican border. As for Canada, it too is in the midst of a prohibition experiment, but on more of a province basis, meaning there's plenty of legal booze up north. For instance, British Columbia ends its prohibition efforts in 1921, and wouldn't you know it, tourism from Americans living in the Pacific Northwest really takes off.
So much so, in fact, that BC gives up the British tradition of driving on the left side of the road to drive like Americans do on the right. Ah, you know Canadians. So polite. So kind of them to accommodate the American tourists who understand that the BC abbreviation really stands for bring cash and may happen to purchase large quantities of perfectly legal Canadian whiskey.
And sure, that whiskey ceases to be perfectly legal once it crosses the border, likely in an automobile's false bottom or removable seats, but that's a problem for Uncle Sam, not Johnny Canuck. Speaking of tactics, some road-bound bootleggers focus less on hiding their liquor and more on outrunning the cops. And that means modifications.
In the words of Edmund Fahey, quote, heavy loads hauled over the toughest of roads, often at reckless speeds, kept the rubber on your car always under the utmost strain. Close quote. Now, the idea that NASCAR directly arises out of these supercharged bootleg mobiles retrofitted with larger pistons is a bit of a stretch. It ignores the stock car racing tradition that goes back to the first wrenchers eking out a little extra horsepower from their Model Ts.
But it is true that a number of future mechanics and racers, like Junior Johnson, later credited with inventing the skidding 180 degree bootleg turn, get their first taste of speed while racing over hills during prohibition. That's right, hills, not just borders, because not all of America's illicit liquor is coming from abroad. Moonshiners, that is, those distilling their own hooch at home, are running stills all over the country.
They might double as bootleggers, running that booze elsewhere or serve customers from their "home speaks" or "blind pig" to use the heiress slang for the at-home speakeasy. Such bootlegging moonshiners are found all across the nation. Even in the deserts of rural Sanpete County, Utah, one local will later claim that "bootleggers almost had to wear badges so they wouldn't sell to each other."
And with so much moonshining going on, it's just a matter of time before an agent comes across an operation, even when that agent isn't trying. It's a late summer evening, May 17th, 1922. Dressed in a vest and flat-brimmed Stetson, a 44-year-old mustachioed prohibition officer named Ben Holter is driving with an unnamed partner on Nettie Street in Butte, Montana.
Ben Numbers, among a few state prohibition officers, recently made federal agents, which is no surprise. He's made a number of successful busts. Even so, I doubt Ben's mind is on bootlegging right now. Enjoying the road, his mind is likely 200 miles away in Whitefish, Montana, on his wife, Clara, and his four kids playing on tree stumps outside their home. Yeah, he's stoic and tough, but the Norwegian-born agent is a family man through and through.
Suddenly, Ben is rocked back to the present as the car's front ax breaks. They come screeching to a halt. Damn it. Look at the damage. Ben knows there's nothing to do but call a tow. Well, one house on this street has its lights on. Maybe they've got a telephone too. He walks over to 2705 Nettie Street and knocks on the door. 23-year-old Madvagen answers. Ben must be relieved to see a phone mounted on the wall behind her.
He tells her about his car and asks to call a tow truck. Maude replies, "We have no phone." She then shuts the door. Wow, that's a bold lie. But as Ben stands there, unsure of what to do, two officers, Charles Rhoda and John Gary, happen by. Then the three of them notice two women slipping out the back of Maude's house. Huh. Ben waits while Charlie and John investigate. Then, only two minutes later, Maude opens the door.
Defeated, she invites Ben in, saying, "Go ahead. They'd found it anyway." Heading upstairs, Ben finds that the "it" is a 20-gallon still along with jars of mash and moonshine. Ben takes samples for evidence and destroys the rest while Maude, a five-time divorcee using a false name, wishes she'd never answered the door tonight. Just another day for Ben Holter. Frankly, Maude wasn't even inventive.
On other occasions, Benz found stills and illegal liquor behind false walls in a home, in a secret concrete chamber under a chicken coop. And last April, the stoic agent trudged through waist-deep snow to deal with a mountain still that sent casks of booze down the slopes on skis. In short, moonshiners are everywhere. But does catching them even matter? The usual penalty is a relatively small fine. Maude's penalty is $100.
And while I can't tell you what happens to her after this, it's fair to guess that she just fires up another still and continues her illicit side gig. Ben sees this pattern all the time. Indeed, after a much bigger raid in which Ben seizes 800 gallons of mash and a 50-gallon still, the bold bootlegger grins from ear to ear as he tells the earnest prohibition agent that they'll, quote, find a new location and start anew, close quote. And Ben knows he's right.
As courtrooms fill with bootleggers and moonshiners, over-tasked judges are happy to slap the perp with a fine and quickly move on. The truth is that the nation's mere 1,500 prohibition agents, all earning a modest salary of $1,500 to $3,000 per year, are facing a Sisyphean task. They're understaffed and underfunded as everyone tries to pass the buck.
Congress wants the states to allocate the funds necessary to enforce prohibition, while the states say that, as a constitutionally imposed mandate, the federal government should foot the bill. In fact, some states are making zero effort at all. Oh boy. And so, prohibition agents fight the underfunded fight. The often unpopular fight, with few seeing the success of New York's Izzy Einstein or even Montana's Ben Holter.
But prohibition is more than an uphill battle against small-time moonshiners and bootleggers. When it comes to the big boys, to the more organized, large-scale criminals, well, that's where things get far more deadly. This message is sponsored by Greenlight.
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Before Prohibition, 1,300 American breweries supplied the nation with full-strength beer. By the mid-1920s, they're all out of business or have pivoted in a serious way. And I'm not just talking about brewing less than 0.5% alcohol per volume near beer. Coors produces malted milk and porcelain pottery. Anheuser-Busch is putting out refrigerated truck bodies and ice cream.
If you're going to buy your ice cream from a repentant brewer, though, I suggest Yinglings. Word has it that theirs is next level. Malted syrup, soft drinks, candy, cheese. Brewers are doing whatever it takes to eke out a living.
But with the nation's large law-abiding breweries and distilleries mostly or completely out of the alcohol business, other, shall we say, entrepreneurs possessing the organization, supply chain, and business know-how are happy to fill this booze business void. I am, of course, referring to the underworld of organized crime. And one of the finest early examples of this is a German-born pharmacist and lawyer named George Remus, aka the King of the Bootleggers.
In his pre-prohibition life, Remus, as he likes to call himself while talking in the third person, was already a gifted lawyer. He popularized the temporary insanity plea a few years back. But it's his pharmacy background that launches his bootlegging career. As we've already established, the Volstead Act allows hard liquor for medicinal purposes. And oh, does Remus see opportunity here.
Setting up in Cincinnati, he purchases distilleries, sets up a drug company, and obtains the proper licenses for medical or bonded alcohol. Then comes the genius part. As his own supplier, he arranges for his own trucks to get robbed. Remus then turns around and sells that booze as a bootlegger and pockets the profits. Thus begins the king of the bootleggers' ascent. Remus's empire grows and soon makes him a millionaire.
He leaves his wife in favor of his likewise married and soon divorced secretary, Imogene. The two become celebrities known for their lavish lifestyle, including a New Year's party with $1,000 bills under every plate, gold watches as parting gifts for the men, and Pontiacs for the women. But all that comes to a stop in 1925 when the law finally catches up with Remus and he's sent to prison. It gets worse. While there, star prohibition agent Frank Dodge interviews Remus about his bootlegging empire.
The portly criminal is soon convinced that he can bribe Frank to get parole. To that end, Remus asks the corrupt warden to put the agent in touch with his beautiful wife, Imogene. Alas, she falls head over heels for Frank who, in turn, goes corrupt and convinces her to run off with him and her incarcerated husband's money. Damn, that is cold. Remus thinks so too and as he gets out of prison in 1927 and receives divorce papers, he begins exchanging lawsuits with his soon-to-be ex.
Well, he's not liking this. Remus thinks they should meet up. Just to talk, of course. It's a pleasant fall morning around 8:00, Thursday, October 6th, 1927. We're just a block away from the stone and red brick Alms Hotel in the Walnut Hills district of Cincinnati, Ohio, where a disappointed and angry George Remus is climbing into the backseat of a borrowed blue Buick touring car. He's frustrated.
Remus sent a courier to the Alms Hotel where his spies tell him that Imogene has a room, hoping to arrange a conversation about their assets before their divorce proceedings go forward later this very morning. That's all he wants, or so he claims. But the messenger was turned away. So now, the ever-determined 51-year-old king of the bootleggers is sitting in this car, his henchman and driver, George Klug, at the wheel, watching for Imogene. Suddenly, Remus spies a lithe, dark-haired woman exiting the Alms Hotel.
That's her, that's Imogene. But she's not with her suspected new lover, Frank Dodge. She's with her 19-year-old daughter, his stepdaughter, Ruth. Both dressed all in black, the two are smiling and laughing as they get into a cab and start to drive off. Remus's temper flares. He nearly lunges at the driver as he shouts, "Run them down if you have to!" The henchman floors it, shooting across Victory Street and cutting off morning commuters.
But in careening through the traffic, the blue sedan draws Imogene's attention. She instantly knows who's in the car, barreling toward her. She exclaims to Ruth, "There's Remus." Ruth urges the cabbie to drive faster, shouting, "Go ahead!" Soon, the two cars are next to each other. In a fit of rage, Remus grabs the wheel and hurls the blue Buick toward the cab, forcing both vehicles onto the grass of Eden Park. The cabbie guns it, tearing divots into the manicured lawn.
The Buick does the same. Both cars hurtle through the usually picturesque open space until the king of the bootleggers car manages to pull ahead and cut off the cab just 12 yards from Mirror Lake. Pushing her daughter back in the cab to keep her safe, Imogene abandons the vehicle and flees on foot. Children, parents, and couples scream and flee as Remus leaps from his car and follows. Though a heavy set man, Remus is quick. He catches up and seizes Imogene by her delicate wrist.
Imogene twists and pulls. Remus only squeezes tighter as he swears and screams. Onlookers are too terrified to move as they watch the powerfully built bootlegger brutally punch his light-framed estranged wife in the face. Remus then pulls her close and draws his pistol. Terrified, Imogene pleads with her enraged husband. Oh, don't hurt me, daddy. You know I love you. Don't do it, don't do it.
But Remus is too far gone. He only pulls her closer and shouts out, "You degenerate mass of clay, take this!" and fires point-blank into Imogene's abdomen. With his wife's blood spilling out, Remus drops her to the ground. Heartbroken, Ruth helps her blood-soaked but breathing mother to the hospital. On the operating table, Imogene ekes out, "My God, do you think I'm going to die? Oh God, I don't want to die."
But it's too late. She dies two hours later. Meanwhile, Remus, in a daze, heads to Cincinnati's District 1 police headquarters and announces, "I just shot my wife and I came to surrender." As he talks with Chief Detective Emmett D. Kerrigan, the king of the bootleggers, tells him with a shrug, "She who dances down the Primrose Path must die on the Primrose Path. I'm happy. This is the first peace of mind I've had in two years." Remus goes to trial.
Despite the testimonies of Ruth, the many witnesses in Eden Park, and Remus' own initial confession, the sly, self-representing lawyer and bootlegger is able to paint himself as the victim using his favorite plea: temporary insanity. The prosecutor, former President William Howard Taft's son, Charles Phelps Taft II, does his best, but when it's all said and done, the jury deliberates for just 19 minutes before declaring Remus not guilty.
He spends seven months in an asylum, goes back to the law, and again marries his secretary. He'll then disappear from the public eye, passing away in 1952 at 73 years old. While Remus's career rose expressly because of Prohibition, make no mistake. Organized crime has a long and storied history before the United States' 18th Amendment. Gambling, prostitution, racketeering, gangs have long had plenty of other illegal pursuits.
That said, prohibition is a gift to organized crime and across the nation, from Detroit's predominantly Jewish purple gang to Boston's Charles King Solomon and on. Gangs and crime lords quickly move into the new black market of alcohol. It pairs in a synergistic way with their other endeavors, particularly prostitution.
Now, the examples and directions we could go from here are almost endless. But we'll take our first seedy step into the underworld by meeting one of New York's most charming killers of the 1920s. Jack Legs Diamond. The son of Irish immigrants, Jack grew up in Philadelphia. What turned Jack and his brother Eddie toward the world of crime isn't readily apparent, but turn they did, running first with Philly's petty thieving boiler gang.
As a 16 year old, Jack excelled at snatching packages delivered at nightclubs and darting off without getting caught. Basically, if he had lived in the online delivery world of the early 21st century, Jack would have been a porch pirate. And it's his ability to sprint with lifted packages or cases of beer that yields his famous lifelong nickname, Legs. Legs was called upon to serve his country during the Great War. Uninterested, he was arrested for desertion and served a stint at the Leavenworth Military Prison.
He only got harder here as he met and mixed with New York gangsters. Upon his release, Legs and his brother become bodyguards and gunmen for hire. The slender, dark-featured gangster is soon racking up charges including assault and grand larceny. Yeah, Legs beats the charges nearly every time and is as charming as they come, but make no mistake, he isn't a good guy.
Moving up the mobster chain, Legs Diamond is soon rubbing shoulders with New York City's most notable mobsters, including one whom we'll meet in more detail a bit later. Sicilian-born Charlie Lucky Luciano. But let's not get ahead of ourselves. This evening, Legs is out with his first underworld boss, a New York gangster with a thriving kingdom built on narcotics, bootlegging, and the garment racket. The one and only Jacob Littleoggi Organ.
It's a crisp fall evening, just about 8:30 p.m., Saturday, October 15th, 1927. The dapper and youthful-faced 34-year-old Jewish gangster, Jacob Organ, or Little Augie, is walking down Delancey Street with Jack Legs Diamond. Now, Legs is highly valued by Little Augie,
The lanky, filly transplant is respected and feared throughout New York and serves as a lieutenant in Little Augie's underworld empire, even running his own speakeasy called the Hotsey Totsy Club. Frankly, the bodyguard gig is a little beneath Legs these days. This is usually his brother Eddie's job, but seeing as he's indisposed due to some run-ins with the law at the moment, Legs is happy to fill in and keep an eye on the boss this evening. Sources don't say what they're up to. The boys might be leaving a business meeting,
griping about competitors like aspiring garment racketeer, Lepke Buckalter, and beer baron, Dutch Schultz, or heading to one of the Big Apple's many speakeasies for a night out. But wherever they're headed, or however sober they are, little Augie has, as always, put a lot of faith in the Irishman. Legs is the only one packing. The duo soon reach a corner and turn onto Norfolk Street. As they start walking up it though, a car begins creeping behind them slowly.
Neither Legs nor Little Augie seem to notice this, nor do they notice when the vehicle stops and three men get out, sneaking up behind them. Suddenly, shots ring out. Men, women, and children scream and run for cover. Little Augie barely has time to attempt to cover his head as his lead-filled body crumples. But even this proves futile as one bullet tears through his right temple. The three gunmen dash back to the waiting car. They peel out, leaving Little Augie dead on the pavement.
Next to him is Legs, who's been hit twice just below the heart. Like his dead boss, the bodyguard is covered in his own blood. While there are some variations on the accounts of the shooting, the outcome is the same. Little Augie is dead. Meanwhile, blood-soaked Legs is taken to nearby Bellevue Hospital. "Incredibly," he pulls through. This is merely one of many attempts to kill Legs.
It's said he carries so many bullets in his body that he jingles while walking, and the fact that he never dies leads the press to dub him the Clay Pigeon. But he ain't talking. When the police question Legs about the shooting, he answers with as much gusto as his shot-through chest can muster. Don't ask me nothing. You hear me? Don't ask. And don't bring anybody in here for me to identify. I won't identify them even if I know they did it. And he does know.
This was likely the work of Lepke Buckalter and Gero Shapiro. Legs will make peace with them, allowing Lepke to replace his dead boss as New York's new kingpin of garment racketeering. This just isn't a fight Legs is interested in. He prefers bootlegging. But that just means other fights. The speakeasy-owning Irishman is soon in a booze turf war with Dutch Schultz. Legs and the Dutchman do their best to kill one another over the next few years. Both sides collect dead bodies, but not the bosses.
That said, everyone's number is up at some point. On December 17th, 1931, Legs goes out to celebrate yet another acquittal with plenty of booze. He then drunkenly stumbles into bed sometime after midnight on December 18th. Once he's asleep, assassins, likely working for Dutch Schultz, unload on him at point-blank range. Thus ends the Clay Pigeon. Well, to an extent that is. His legend will live on in books and film.
But speaking of films, I think it's time for us to meet some other New York gangsters. To hear their tales of friendship, families, and all-out war. You might say it's a story that you can't refuse.
Thank you.
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Possibly derived from an Arabic word that came to Sicily during the brief period of Islamic rule over a thousand years ago. Possibly derived from the nickname of a 17th century Sicilian witch. The word mafia is believed to have originated on the Italian island of Sicily and means something along the lines of boldness or swagger.
Whatever the origin of the word, it became attached to the Mediterranean islands several gangs in the 19th century as they banded together against the much despised Bourbon monarchs who ruled much of southern Italy prior to its unification in 1871. In fact, this mafia soon became Sicily's de facto government, enforcing law, collecting taxes, and dealing justice. All according to its own code, of course. A code of hierarchy and secrecy. The mafia didn't stay on the small island, though.
As hard times spurred Sicilian emigration, many of whom, as you may recall from episode 118, found themselves passing through Ellis Island to make a new life in the United States, and particularly in New York, the mafia spread with them. Let's keep this in mind as we take in a bit of pre-prohibition background on one particular Sicilian immigrant destined for big things in this American-based mafia.
Salvatore Lucenia, as he was first known, was only nine years old when his Sicilian family made the transatlantic steerage class voyage to Ellis Island in 1907. They soon settled on the Lower East Side of New York, but the dark-featured youth didn't care much for it. As he saw it, his family had merely traded poverty on their home island for poverty in a trash-filled slum where he can't even speak the language. Frustrated, Salvatore turned to petty theft at the tender age of 10.
He dropped out of school by 14. Now it's important to note that Salvatore's childhood was one of ethnically divided immigrant neighborhoods. There's Chinatown. The Italians had their own Little Italy. While Eastern European Jews were sandwiched between the Italians and the Irish. Yet, despite their ethnic or religious dividing lines, many children in these struggling neighborhoods were learning the same lesson. That crime does, in fact, pay.
pickpocketing, craps games, muggings. This was their world and by his late teens Salvatore had taken a liking to using extortion tactics on Jewish kids. He and his fellow young Italian thugs would isolate a Jewish youth then let the kid pick between a beating or quote-unquote paying for protection. Well, one day Salvatore presented his offer to a particularly small Eastern European Jewish boy.
The teenage Italian threatened, "If you want to keep alive, Jew boy, you gotta pay us five cents a week." The diminutive child answered with bold defiance, "Go f*ck yourself." That boy's name was Meyer Lansky. Various versions of this meeting of young criminal minds carry various apocryphal details, but the simple and important truth is that this failed attempt at extortion proved the beginning of a deep, abiding, and soon law-breaking friendship between the two.
In a rather monumental step for the era, Salvatore crossed the ethnic divide to ally with this small but fierce Jewish kid who had a head for numbers. And with Meyer came his hard-fighting best friend, Benny, or Bugsy Siegel. Growing into teenagers, Salvatore, Meyer, and Bugsy merged their Italian and Jewish gangs to fend off the better established Irish gangs.
Meyer and Bugsy rigged street games while Salvatore, who was also running with the Five Points Gang and getting mentored by fellow Italian Johnny Torrio, got arrested for dealing heroin in 1916. After a six-month stint in prison, Salvatore, or Charlie as he now prefers, after other inmates shortened his name to Sal or Sally as they tried to make sexual advances on him, returned to the streets with more cred for not squealing on his associates while in the slammer.
The Five Points Game reward newly christened Charlie with full membership. This allowed Charlie to rub shoulders with another young gangster who would soon follow Johnny Torrio out to Chicago, a guy named Al Capone. I know, Charlie has barely reached adulthood, yet has already met or worked with half of the era's legendary gangsters. But enough background. As Prohibition begins in 1920, Charlie parts ways with the Five Points Game. He's now running with a true mafioso, that is, a true Italian gangster.
Giuseppe Masseria, otherwise known as Joe the Boss. A Sicilian immigrant whose criminal life began on his home Italian island, Giuseppe Joe Masseria quickly applied his mafia know-how upon arriving in New York. As Prohibition starts, he's already wealthy, powerful, but also very old country in his thinking. He's a mustache Pete, as the mafia's older and mustachioed generation is known.
As such, Joe expects his men to show him great deference and is not a fan of working with non-Italian gangsters. As the years progress, these old country ways become increasingly irritating to younger members of the mafia, particularly to Charlie Luciano, or Charlie Luciano, or Charlie Lucky Luciano, as he's not only changed his last name, but picked up a nickname.
Yes, this is the guy we first met as Salvatore Luciano. And I know, this guy goes through names like you go through smartphones, updating every few years. Anyhow, this particularly irritates Charlie Lucky Luciano. As we know, he values his friendship and business relationships with Jewish gangsters Meyer Lansky and Bugsy Siegel. Charlie and other young Turks, as the upcoming generation of the Mafiosi are known.
Think more along the lines of the full-on genius Jewish gangster Arnold Rothstein, allegedly the man who rigged the 1919 World Series and definitely F. Scott Fitzgerald's inspiration for the handsome, debonair character Meyer Wolfsheim in The Great Gatsby. Arnold doesn't believe in letting ethnicity or religion get in the way of a good deal. He invests in Irish gangsters like Jack Legs Diamond just as readily as he invests in Italian-born Charlie and so on.
In fact, he might be the one behind the Seven Group, aka the Big Seven, a collection of major gangs that, around 1927 or 28, begins pushing for a more diplomacy-first-shoot-second approach amid all the obscene violence and murder brought on by bootlegging. It isn't that the younger generation is opposed to violence and killing, but these up-and-coming gangsters have simply seen so much of it since Prohibition began that they're putting illicit business ahead of prejudice.
As Meyer Lansky puts it, we were in business like the Ford Motor Company. Shooting and killing was an inefficient way of doing business. Ford salesmen didn't shoot Chevrolet salesmen. They tried to outbid them. But there's more trouble than this generation gap. The ambitious leader of a rival mafia faction in Brooklyn, Salvatore Maranzano, is growing a bit too powerful for Joe the Boss' liking.
In February 1913, an Italian on Italian turf war, known as the Castelabarese War, breaks out. Charlie is not a fan of this war. Again, this young Turk mafioso, who now runs nearly all prostitution in New York, is quite capable of violence. But as he sees headline after headline about this inter-mafia turf war in the newspapers for more than a year, Charlie also sees lost dollar signs in his mind.
So he goes to see his own boss's enemy, Salvatore Maranzano, to see if this thickly mustachioed, Brooklyn-based boss is amenable to ending the violence. He is, and soon, a plan to do so is put in motion. It's about one o'clock on a bright spring afternoon, Wednesday, April 15th, 1931. Giuseppe Masseria, or Joe the Boss, is just pulling up to 2715 West 15th Street in Coney Island.
This is a brand new Italian restaurant, Nuova Villa Tamaro, and the seafood is so good you'll kiss your mother. Accompanied by two bodyguards, Joe steps out of his steel armored sedan. Joe enters the restaurant, flashes a smile at the owner's mother-in-law, Mrs. Anna Tamaro, and joins his already seated trusted lieutenant, Charlie Lucky Luciano. We don't know the details of the meal, apart from Joe's appetite, that is.
He wolfs down his spaghetti with red clam sauce and lobster. He gulps plenty of Tuscan red wine. Meanwhile, Charlie just picks at his food. As the talking meal wraps up, Lucky suggests they play some cards. Joe agrees. But as the cards come out, first Lucky says he needs to hit the men's room. Hey, when you gotta go, you gotta go. Returning from the bathroom,
Charlie finds Joe the boss's heavy body sprawled on the floor with several bullet holes in his back and head. The boss pulled the tablecloth down as he died, and cards littered the blood-stained wooden floor. Good. It's just as Charlie and the boys planned. They plant an ace of spades in Joe's lifeless hand. We suppose. Then walk out and drive off.
Legend will put Charlie at the scene when the cops arrive, mournfully explaining that this all happened while he was in the bathroom, barely able to hear much apart from the gunshots over the running tap water. But that's just legend. He likely left with the gunmen, who, we think, were Bugsy Siegel, Vito Genovese, Albert Anastasia, and Joe Adonis. So much ambiguity though. I guess all we can say for sure is that Joe the boss has eaten his last meal.
With Joe dead, Salvatore Maranzano is ecstatic. The Brooklyn-based boss holds a meeting in an enormous hall in the Bronx for all 500 of his men. With a massive crucifix over his head, Salvatore tells the gathered gangsters that he is now the "capo di tutti i capi," or the mafia's boss of all bosses.
He says New York will be divided across five mafia families, all answering to him and that, quote, whatever happened in the past is over. There is to be no more ill feelings among us, close quote. He goes on to clarify that all senior members of Casa Nostra, literally our thing, and that thing being the mafia, are not to be harmed.
Perhaps to drive home the point that he's in charge, and to show that the past is indeed in the past, Salvatore holds a three-day party in the same restaurant where Joe was killed. He invites mafiosi from across the country. Yet, despite getting named as head of one of the five families, Charlie isn't happy. Salvatore may have given the order, but Charlie is the one who planned and carried out Joe's execution. Moreover, Salvatore is not getting on with the Young Turk agenda.
Turns out he's a bit old-fashioned as well. Another mustache Pete, who prefers to work with Sicilians and is decidedly anti-Semitic. That doesn't work for Charlie. Meyer is not just a friend. He's the brains that got Charlie to where he is today. And if Salvatore is going to waste a gifted mind over some dumb old world rules and prejudice, then he's got to go. At the same time, Salvatore, who's feeling the animosity, is thinking the same thing about Charlie. He tells Joseph Valachi...
We got to get rid of them before we can control anything. To that end, Salvatore is willing to step outside of Sicilian circles to hire an Irishman, Vincent "Mad Dog" Cole, to end Charlie's luck. Ah, but now Charlie's learned of Sal's plan to bump him, so the young Turk mafioso decides to take care of his problem with a degree of irony.
Charlie turns to his Jewish friend Meyer Lansky, who in turn hires a crew of Jewish men to take out Salvatore, specifically a crew out of Toledo led by Samuel Red Levine, a man who wears a yarmulke under his hat when killing on the Sabbath. On September 10th, 1931, four men arrive at Salvatore's office. Some sources say they claim to be with the Bureau of Internal Revenue. Other sources say with Immigration Services.
Either way, Sal invites them in, prepared to offer a bribe. As soon as the door closes, the fighting starts. Salvatore puts up quite a struggle, but in the end, they stab him six times, shoot him four times, and, just to ensure his death, slice Sal's throat. The killers leave the building with no resistance. That same day, Vincent "Mad Dog" Cole comes to see Sal. By some accounts, he passes the four assassins on the way in.
Whatever the truth of it, he finds the man who hired him is dead. So, the Irishman shrugs his shoulders and leaves unaware that he'll soon meet his end as well. A few months from now, Bugsy will put the mad dog down while he's in a telephone booth. With Joe the Boss and Salvatore Maranzano, those two mustache peats, dead. A number of other hits for those still loyal to them go out across the Big Apple, but most are happy to switch allegiances.
By the end of September 1931, Charlie Lucky Luciano could assert that he's the Mafia's new boss of all bosses. But rather than try to wear this blood-soaked crown, he goes a more democratic approach. He calls for the formation of the Commission. Effectively, this is a committee with representatives from the Mafia's five New York families, as well as other representatives from Chicago and Buffalo, forming a confederation of families within the Mafia.
Ideally, this means that if two or more mafia families are in conflict and their respective conciliaris, that is, the chief counselor to a family boss, can't resolve it, this governing body can still sort things out without resorting to a war.
Now, while the mafia remains ethnically Italian, the downfall of the Mustache Pete's allows a mafioso like Charlie to collaborate easily with gangsters outside the mafia, or La Casa Nostra, as it's now known in New York, or The Outfit or Syndicate, as it's known in Chicago, or The Office, to use the New England term. More to the point, Charlie can work with his dear Jewish friends, Meyer Lansky and Bugsy Siegel.
Meanwhile, Meyer, Charlie, and other gangsters of all backgrounds are working on stabilizing organized crime across all ethnicities and gangster organizations in the nation. This starts with that diplomacy-minded Seven Group I mentioned earlier. It's alleged that the nation's top gangster bosses then met in Atlantic City in 1929, though no primary source evidence can corroborate it. But as less grandiose meetings of gang bosses take place, the result is the same.
By the early 1930s, we have the organized crime governing National Crime Syndicate. Its stability is ensured by the supra-organization's assassination arm, soon dubbed Murder Incorporated.
But of course, it's just as the Mafia's commission and the larger gang-governing National Crime Syndicate get going, just as gangsters of all backgrounds and ethnicities start to figure out how defined territories and collaboration can make all of them wealthier, that prohibition gets repealed through the 21st Amendment on December 5th, 1933. That stings since bootlegging is organized crime's biggest moneymaker.
But hey, there's still money to launder, people to extort, prostitution rings to run, gambling to fix, and well, it sounds like organized crime will stay plenty busy even if the golden age of prohibition is gone. But we aren't ready to close the door on this criminal golden age just yet. There's still one bootlegging gangster out in Chicago whose story looms so large over the roaring 20s that it needs its own episode. How does Sean Connery put it?
They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. That's the Chicago way. That's right. Next time, we're heading to the Windy City to meet Al Capone as he battles it out with Prohibition agent Elliot Ness and his Untouchables. ♪♪
History That Doesn't Suck is created and hosted by me, Greg Jackson. Episode researched and written by Greg Jackson and Will El Tigre Número Uno King. Production by Airship. Sound design by Molly Bach. Theme music composed by Greg Jackson. Arrangement and additional composition by Lindsey Graham of Airship. For a bibliography of all primary and secondary sources consulted in writing this episode, visit htdspodcast.com. Thank you.
