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Authors: Tim Newark

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A later probation report declared that he had already acquired a “definite criminalistic pattern of conduct” by this age. “His freedom from conscience springs from his admitted philosophy: ‘I never was a crumb, and if I have to be a crumb I’d rather be dead.’ He explains this by stating that a crumb is a person who works and saves and lays his money aside; who indulges in no extravagance. His description of a crumb would fit the average man.”
When he came out on parole after six months, Lucania was acclaimed as a “stand-up guy” by his criminal associates. He’d taken his punishment like a man and hadn’t squealed. He also had a new name. He didn’t like the fact that Salvatore could be shortened to Sal or Sally. It invited sexual advances from convicts. Besides, he was an American gangster now and he wanted an American name, so he took up “Charlie” and became Charles Lucania. That was the name that would feature on his police reports over the next decade.
Lucania went back briefly to his shipping clerk job, but finally quit when he won $244—nearly a year’s wages—in a floating craps game. For him, crime paid, and that was an end to his honest living.
 
 
Just as the teenage Charlie Lucania was forging his reputation, so other notorious gangsters were also on the rise. “Terrible” Johnny Torrio was in his teens when he first came to prominence in the Lower East Side. He was a short, tough Italian, whose ruthless skill with his fists and knives got him a job as a bouncer at Nigger Mike’s bar. He became a lieutenant to the Five Points Gang leader, Paul Kelly, the Italian with an Irish name. Hungry for his own criminal territory, he took over a bar and brothel for sailors in Brooklyn. He took a liking to an effective street fighter called Al Capone and kept him close to him. In 1915, when Torrio was thirty-three years old, his uncle, “Big Jim” Colosimo, offered him a job in Chicago, looking after his extensive vice operations. Four years later, he called on Al Capone to join him there.
Capone was two years younger than Lucania, born in Brooklyn to Neapolitan immigrant parents. At school, he beat up his teacher and quit. He joined Torrio’s James Street Gang and also got to know Lucania. The two became firm friends. Capone got his nickname “Scarface” after a fight in a bar over a girl when he got his left cheek slashed open. By 1919, he was a professional
murderer and was happy to escape police interest in New York to join the older Torrio in Chicago.
On January 16, 1920, came Prohibition—the biggest break for organized crime in the United States. Campaigners against the evils of alcohol had succeeded in getting the government to introduce a ban on the sale of liquor. Almost immediately, illicit drinking bars called speakeasies sprang up in major cities and these had to be supplied with bootleg booze. The gangs stepped in to ensure this supply and made a fortune over the next thirteen years. Some of the money was used to bribe police and the legal system, as many of those entrusted with upholding the ban were happy to turn a blind eye to it, especially if it lined their pockets. It introduced a level of corruption into public affairs that enabled criminal gangs to get a firm grip on the American metropolis.
In Chicago, Big Jim Colosimo did not see the golden opportunity straightaway and clashed with Johnny Torrio over supplying illicit booze because he didn’t need the extra cash and the risks that came with it. With Capone at his side, Torrio organized the assassination of Big Jim. The way was now clear for them to take over the bootleg business and make themselves immensely rich. While Capone organized the strong-arm stuff, Torrio took on more of a management role and realized that the old way of street gangs fighting each other for a piece of the action was a waste of everyone’s effort, especially when there was so much money to be made from Prohibition. He called together many of the Chicago gangs, regardless of their ethnic background—Italians, Irish, and Poles—and divided the city up so that each gang had its own territory, secure in knowing that no one else would mess with them. That way, they could concentrate on shaking off the police and bringing in the cash.
Of course, not everyone went along with Torrio’s business model. The Irish North Siders led by Dion O’Banion double-crossed Torrio, and others cheated him. But the main proposition was not a request—it was a threat. Join up with this plan or
face annihilation. Most of the time Torrio got his way, but in 1925 his luck ran out and he was ambushed in his limousine, nearly killed by a shotgun blast and four pistol bullets. Out of the hospital, he told Capone he was retiring and left Chicago to Scarface.
Back in New York, other powerful criminal characters were emerging out of the underworld. The Lower East Side was rich in Jewish gangsters such as Meyer Lansky. He was born Maier Suchowljansky in 1902 in Grodno, Poland. His parents fled pogroms there and Lansky fought anyone who tried to intimidate him in America. His family had had a bellyful of that. As he formed his own teenage Jewish gang, the small-statured Lansky got together with a tall, good-looking boy called Benny Siegel, who was three years younger. Quick to anger, Siegel had a formidable reputation as a street fighter and was happy to use a gun from an early age. Lansky saw this both as strength and weakness.
“His big problem was that he was always ready to rush in first and shoot, to act without thinking,” said Lansky. “That always got him into trouble. I explained patiently to him again and again that if you’re going to succeed, it’s better to work from behind the scenes.” It was advice that Lansky would take himself, but Siegel was too much of a hothead to stay out of trouble for long. According to Lansky, his best friend got his moniker “Bugsy” because he was “crazy as a bedbug.” A later FBI report said he “acquired his title of Bugsy because many of the associates in the old days considered him as ‘going bugs’ when he got excited in that he acted in an irrational manner.”
Lansky and Siegel turned their teenage gang into muscle for hire and made a fortune in the early years of Prohibition. They offered protection to bootleggers or hijacked their shipment if they failed to come through with the cash. In their gang were other hoodlums who made names for themselves, including Abner “Longy” Zwillman, Louis “Lepke” Buchalter, and Arthur
Flegenheimer—who became famous as Dutch Schultz. Ever since they’d met as kids in the Lower East Side, Lansky and Charlie Lucania had kept up their friendship, but the time was not yet right for them to come together as a powerful criminal alliance.
In 1920, the king of the New York underworld was a stocky, five-foot-two Sicilian called Giuseppe Masseria, known as “Joe the Boss.” Fleeing a murder charge in his homeland, Masseria had joined the Morello gang, an early Mafia crime family based in East Harlem. When their top killer, Ignazio Lupo “the Wolf,” was jailed, Masseria had taken over the gang and his influence extended throughout Manhattan and into Brooklyn. When Lucania’s and Lansky’s gangs clashed with his soldiers in the Lower East Side, Masseria recruited the up-and-coming Sicilian as a gunman, but told him to ditch his friendship with Lansky. As an old-style Italian Catholic, he hated Jews.
On August 8, 1922, Masseria was at home on the Lower East Side in his three-story brownstone house on Second Avenue near East Fifth Street. Just after midday, a blue Hudson touring car stopped outside a kosher butcher’s shop nearby. Two men stepped out of the car and walked into a restaurant across the road from Masseria’s house. One of the men was thirty-four-year-old Umberto Valenti, a veteran hit man and associate of Peter Morello, who resented Masseria taking over his gang. Two months earlier, Joe the Boss had knocked off Mob rival Silvio Tagliapanna, and Valenti was looking to equalize things.
For an hour, Valenti and his accomplice toyed with cups of coffee and slices of cake, keeping a sharp eye on Masseria’s house. At just after 2:00 P.M., the tubby Italian Mob boss sauntered down the steps of his brownstone. He was wearing a light summer suit and straw hat. He turned north to stroll along Second Avenue. Valenti and his friend bolted out of the café and strode after Masseria. As Joe the Boss spotted them, Valenti pulled his weapon. Unarmed, Masseria tried to dodge inside a hat shop but was caught outside a women’s clothes store.
“The man with the revolver came close to the other fellow
and aimed,” said one of the shop owners. “Just as he fired the man jumped to one side. The bullet smashed into the window of my store. Then the man fired again and this time the man being shot at ducked his head forward. Again the man fired and again his target ducked his head down. The third shot made a second hole in the window.”
How Valenti, a professional gunman, could miss three times at point-blank range is a mystery, but it gave Masseria the nickname “the Man Who Could Dodge Bullets.” Joe the Boss didn’t hang around to wonder why and sprinted off toward his home. Seeing witnesses gathering, Valenti and his accomplice ran back to their parked car. As their Hudson careered down the road, they were confronted by a crowd of striking garment workers pouring out of a hall near the Bowery.
“The gunmen realized that an attempt to ram their way through the throng would take time and might prove unsuccessful,” said a newspaper report. “They resorted to more desperate measures. Two of them got on the running board and fired point-blank into the crowd.”
Some twenty shots were fired. Eight of them hit home, wounding the striking men—one died later. Panic spread down the street, especially when some of the garment workers fled into a nearby nursery school. A policeman commandeered a car and chased the gunmen north, but at East Thirty-second Street, the Hudson cut ahead of other vehicles in the dense traffic and escaped.
In the meantime, Masseria was sitting on the edge of his bed at home, poking a finger through the two bullet holes in his straw hat. A few hours later, he sent out a message to call a meeting with Valenti and his cronies to make things right. But he had no intention of turning up to face his incompetent assassin. He ordered three of his young gunmen to make the meeting. One of them was most likely the twenty-four-year-old Charles Lucania—ambitious to do some high-profile business for his boss.
Three days later, around midday, Masseria’s men met with Valenti and his gunmen on the corner of East Twelfth Street and Second Avenue, not far from where Lucania’s family first lived when they came to America. It was a heavily Jewish populated area and witnesses were shocked at the sudden explosion of violence as the group of mobsters broke apart and started firing at each other. An eight-year-old girl playing outside her grandfather’s store was hit in the chest in the crossfire. A road sweeper fell into a gutter seriously injured. Almost everyone else ducked for cover as Valenti ran out into the road and jumped on the running board of a taxicab. But one gunman stayed calm and stood rooted in the middle of the road, aiming carefully, firing methodically after the fleeing mobster.
“It was the coolest thing I ever saw,” said a teenager. “People were shrieking and running in all directions, and this fellow calmly fired shot after shot. He did not move until he had emptied his weapon.”
The ice-cool gunman was determined to complete his job. When Valenti pulled out his Colt to fire back, he was struck in the chest. He collapsed from the side of the taxicab, mortally wounded, blood pouring through his shirt. As police rushed to the scene, a passerby indicated the hallway of a tenement block into which the assassin had disappeared. The police ventured into the dimly lit building, but the gunman had climbed a ladder at the rear to escape into a yard—he knew his way too well around the neighborhood. A witness later described him as young, short, dark, and neatly dressed. It had likely been Charlie Lucania. Emerging out of the shadows, he was fast becoming one of the deadliest mobsters on the street.
As an expert gunman, Lucania had bought a country cabin near Nyack, on the banks of the Hudson, north of New York City. There, he and his mobster friends practiced their shooting skills while hunting and blasting off rounds from machine guns.
Lucania thrived under Joe the Boss and made a small fortune out of Prohibition, but he was only a low-level gangster. To earn
serious money and gain the power he hungered for, he had to make friends with another legendary villain, Arnold Rothstein—known variously as “Mr. Big,” “the Big Bankroll,” and “the Brain.” The lessons Lucania learned from Rothstein would put him on the road to becoming king of the New York underworld.
UPTOWN GAMBLER
T
o rise above the level of an ordinary hoodlum, Charles Lucania had to make a connection with a patron of crime—an enormously rich and influential underworld potentate who could link the Lower East Side with uptown Manhattan. None came bigger or more powerful than Arnold Rothstein—the original Mr. Big. This man has been credited with founding organized crime in New York City. Small-time gangsters had paid off local policemen to turn a blind eye to their activities. Rothstein took graft to a whole new level by dealing directly with politicians, paying them to alter the legal procedure. During Prohibition, he intervened with well-placed payments to get thousands of court cases dismissed.
Rothstein directly invested in the enterprises of leading bootleggers such as Jack “Legs” Diamond, Dutch Schultz, and “Waxey” Gordon and made sure they were protected from prosecution. He established good relations with European distilleries to bring in high-quality liquor and when he foresaw that
Prohibition would come to an end, he promoted international networks importing narcotics. Any up-and-coming mobster sought his favors and this included Johnny Torrio in Chicago and Lower East Side newcomers Charlie Lucania, Meyer Lansky, and Frank Costello. Above all, Rothstein liked to keep out of the limelight and that was the very best advice he could give to any aspiring crime boss.
Although he moved in rarefied circles in the 1920s, Rothstein came from the Lower East Side like so many other mobsters on the make. Born in 1882 to a native New Yorker, it was his father, Abraham, himself the son of a Bessarabian Jewish immigrant, who had made the leap from poverty to wealth—but he had done it the law-abiding way, through sheer hard work and business enterprise. So Arnold had a comfortable middle-class upbringing. At school, he excelled at numbers but when he should have been going to Hebrew studies he was out on the streets winning pennies from other kids.
“I always gambled,” said Rothstein in a rare newspaper interview in 1921. “I can’t remember when I didn’t. Maybe I gambled just to show my father he couldn’t tell me what to do, but I don’t think so. I think I gambled because I loved the excitement. When I gambled, nothing else mattered. I could play for hours and not know how much time had passed.”
When his father tried to get him into the family textile business, Arnold just played pool with his father’s employees. He preferred studying people to studying books and believed he could analyze the motives of other men at a glance and get the best of them. He got odd jobs in poolrooms, so named because they were places where lottery tickets were sold and the prize money paid out of the “pool.” Billiards tables were installed to keep lottery customers occupied and the game was adapted for quicker play, resulting in what is now known as “pool.” Rothstein had a talent for the new game and represented the house, sharing the profits with the poolroom owner who always bet on him. As a teenage gambler, he also played dice and poker, using
his winnings to buy friendships with bigger, tougher boys. He had a slim build, was no hard man, and sought out muscle for protection.
As Rothstein’s bankroll grew bigger, he peeled off bills to lend to other gamblers. When they didn’t pay up, he employed Monk Eastman, a street-brawling gang leader, to collect for him. Eastman also delivered votes for the Democrats at Tammany Hall at election time. Thus, Rothstein learned the connection between crime and politics—a relationship he would develop to an extraordinary degree.
Rothstein generated more money by organizing places to gamble. When regular gambling houses were shut down, Rothstein invented the “floating game” that moved from secret location to location. His bankroll just kept on growing. Flashing his hundred-dollar bills earned him respect in what were called “sporting circles,” in which gamblers bet on all kinds of sports from prizefights to baseball and horse racing.
As his personal wealth grew, he moved among more sophisticated New Yorkers and had the conversational skills to match. He was articulate and well informed. The only flashy thing about him was his ever-present bankroll; otherwise he dressed expensively but quietly. He never wore jewelry. He rarely drank, never smoked, didn’t play around with women. “Rothstein rarely exhibited anger,” said a contemporary report. “He might burn with indignation, but he never let it show. The heavy lids of his eyes might narrow a trifle, his pale, heavy face flush ever so slightly, but he kept his tongue under control. He shunned quarrels and if a disagreement arose he would depend on his ability to talk himself out of a tight corner”—or his ability to hire a mobster to do the dirty work for him.
In 1919, Rothstein broke his cardinal rule of criminal discretion when he hit newspaper headlines for the first time. In January of that year, two New York detectives broke into an apartment on West Fifty-seventh Street where Rothstein was playing a high-rolling game with some associates. They’d
knocked on the door but the gamblers refused to open up. Suspecting they were holdup gunmen, the gamblers drew their pistols and fired through the door. The detectives were wounded in the hail of fire and Rothstein was charged with assault. He was released on $5,000 bail—a sum he paid out of the bankroll he carried on him—and a judge later dismissed the case, saying that it was a waste of time and public money with not a word of evidence produced to show that Rothstein had committed an assault on anyone. It set the pattern for Rothstein’s future relations with the law.
The next year, Rothstein made far bigger headlines—as the man who tried to fix the 1919 World Series. The Chicago White Sox was one of the great baseball teams in America at the time. They looked like easy favorites to win the World Series. With millions of baseball fans betting on them, the odds were stacking up against the Cincinnati Reds, but a group of sporting gamblers saw an opportunity. If they could raise $100,000, they could pay off ten Chicago team players to throw the game. Exfeatherweight boxing champion Abe Attell acted as a go-between and approached the Big Bankroll for the money. Did he finance the deal or not? The White Sox threw the end-of-series game and when rumors of the fix got out, a grand jury trial was called in September 1920. There was little evidence to prove that Rothstein was involved. He testified against the leading conspirators and the jury exonerated him of any involvement in the scandalous action of the “Black Sox” intentionally losing the game. What probably did happen was that once Rothstein heard of the conspiracy, he made sure not to be involved, but that didn’t stop him from placing $60,000 on Cincinnati and winning $270,000. That was clever and typical of Rothstein’s ingenuity. For him, intelligence could be as effective as criminal action.
 
 
Even though Rothstein was cleared of any wrongdoing, his brilliance in making money out of the notorious baseball fix added
to his aura of invincibility and attracted young criminal acolytes. “Rothstein had the most remarkable brain,” said Meyer Lansky. “He understood business instinctively and I’m sure if he had been a legitimate financier he would have been just as rich as he became with his gambling and the other rackets he ran. He could go right to the heart of any financial problem and resolve it unerringly. I tried to keep up with Rothstein in reducing every business or financial operation to its basics—I asked his advice, asked questions.”
Charlie Lucania was equally impressed by his discretion. “You gotta stay out of the papers,” he later said, “you gotta pay people good to stick their necks out while you stay in the background. Arnold did that, Frank [Costello] did that, Johnny Torrio did, all the smart ones stayed out of the papers. Even Joe the Boss moved into a place on Central Park West and called himself an importer—and he was a greasy old
cafoni
[peasant].” In accordance with this lesson, Lucania disliked socializing with the more flamboyant gangsters, such as Al Capone, whenever he came to New York in his armor-plated Cadillac. He drew too much attention.
Lucania even aped the Big Bankroll’s personal style. Rothstein gave him advice on how to dress with conservative good taste, how to behave in sophisticated restaurants, and how to act around a lady—“If Arnold had lived a little longer, he could’ve made me pretty elegant,” he joked. It was supposedly Rothstein who gave him a taste for silk shirts, ties, and pajamas purchased from France.
Embarrassed by being forced into the spotlight by the World Series scandal, Rothstein announced his retirement as “Gambling King” in September 1921. “It is not pleasant to be, what some call, a ‘social outcast,’” he told the New York
Mail.
“For the sake of my family and friends, I am glad that chapter of my life is over.” Having made a fortune estimated between $3 and $4 million, he explained that he intended to devote his future life to his real estate business and his racing stables. In reality,
he concentrated on extending his control over New York’s underworld.
Rothstein got into the business of Prohibition-busting through his criminal friends. When they got arrested for supplying illicit liquor, he posted bail for them. From that, he took a little piece of all their enterprises. His massive bankroll enabled him to fund bootleggers and rumrunners. Jack Diamond started out as his bodyguard. When Rothstein acquired the trucks to shift the booze, Diamond took over this business for him. So widespread were his contacts that Rothstein could take care of every aspect of the bootleg business, and that included bribing the necessary politicians and police—even the Coast Guard.
Irving Wexler, known as “Waxey” Gordon, wanted to borrow $175,000 for Rothstein to increase his importation of whiskey from Canada. Rothstein countered by investing more money into the venture by extending the business to importing high-quality liquor directly from Europe. Rothstein was, in effect, merchant banker to the underworld. It was a small step to extending his reach to include the smuggling of narcotics and diamonds into the country.
It was through Jack Diamond that Rothstein exerted his grip over the gangs of New York. In 1919, at the age of twentythree, Diamond started working for Rothstein as a thug hired to settle labor disputes. Strikes had blighted the Lower East Side ever since Lucania and his family first arrived there. To combat the strikebreakers hired by employers, the unions turned to gangsters to help them out—for a fee—and as a result mobsters became closely involved with union officials, eventually putting themselves forward for fixed elections as union leaders.
When the garment district was rocked by a major series of strikes, Rothstein stepped in and many of his key henchmen, including Diamond, got involved in the street battles. At a September 1920 meeting of New York Central Trades and Labor delegates at the Central Opera House on East Sixty-seventh Street, a riot broke out between strikers. “Men ran about, punching each other
in the face indiscriminately,” said a reporter. “In the rear of the hall there appeared to be in progress a free-for-all fight. Several delegates rushed up and declared that one man already had been killed and others were being unmercifully beaten.”
By the mid-1920s Louis “Lepke” Buchalter had usurped the chief union racketeering role from Rothstein. When garmentmaking factories hit hard times and took loans from the Mob, gangsters ended up becoming employers and derived an income from that, too.
From hired thug, Jack Diamond graduated to becoming Rothstein’s personal bodyguard, paid $1,000 a week to protect him from sore losers and ensure that losing “sports” paid up. On the side, Diamond, with his brother Eddie, established their own bootlegging business, often hijacking consignments that had not paid “insurance” to Rothstein. Diamond was a psychopathically violent man who thrived on the adrenaline rush of an armed robbery. One of the top recruits to his gang was Charlie Lucania.
Lucania had already proved himself as an ice-cool hit man for Joe “the Boss” Masseria and been rewarded by promotion within his Mafia organization. He ran Masseria’s downtown gambling rackets as well as continuing his involvement in narcotics dealing and neighborhood protection. On December 15, 1921, he was arrested in Jersey City, New Jersey, for carrying a concealed weapon, but the charge was dropped.
Like most mobsters, Lucania exploited the gold rush provided by Prohibition. He did this in several ways. One was to provide the means by which local residents could brew their own liquor. Nick Gentile was an influential Sicilian-born mafioso, and he recalls how this worked for him. He started by opening a wholesale grocery store.
“The commodities that I sold most were sugar, tin cans and yeast which the bootleggers needed for the distillation of alcohol,” he said. “In a few months, I succeeded in bringing 75% of the bootleggers to my store. In this manner, I succeeded in earning about $2000 a month.”
Lucania and his associates were alert to this and quick to provide similar supplies. Joe Biondo, Lucania’s old friend from the days when they shared an apartment in East Fourteenth Street, devised a method of mixing a liquid with denatured spirits—not prohibited by law—that once distilled became pure spirits. Another scam was to obtain the pure alcohol used in the manufacturing of perfumes. Showcase bottles of perfume were kept by barbers, but the rest of the alcohol they bought from federal storehouses was sold to bootleggers at $15 per gallon, rather than the usual $5 per gallon. Lucania worked alongside Willie Moretti and others to open their own distilleries throughout New York State.
Sometimes this work could be dangerous. Joe Bonanno started off his career as a mobster with a basement distillery that he ran with his cousins. One of them, Giovanni Romano, was working through the night distilling whiskey when the building was rocked by an explosion.

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