Boardwalk Gangster

by Tim Newark

  Over the previous decade, the Lower East Side underworld had been dominated by several well-known criminal characters. There was “Humpty” Jackson, whose gang worked out of East Fourteenth Street. He got his name from his physical deformity—a hunchback—and he wore a pistol in his derby hat. Then there was “Nigger Mike” Salter, who ran a bar in Chinatown and got his name from his very dark Mediterranean coloring. His gang killed “Eat-’em-up” Jack MacManus, who had been lording it over his rivals by wearing an elegant suit and overcoat and carrying a silver-headed cane. MacManus was found dead one night in Houston Street with his head crushed in by an iron bar. He had been a lieutenant to Paul Kelly, chief of the long-established Five Points Gang, who was not in fact Irish but Italian.

  Many of these gangs gained their prestige from their connection with corrupt Democrat politicians from Tammany Hall who paid them handsomely on election days for delivering votes for their party. When these gangs demonstrated their power openly in 1903 by taking over sections of the Lower East Side and raiding saloons, the police moved in strongly and ever after kept them in the shadows with frequent raids on their headquarters.

  A more insidious criminal organization was the Black Hand. They were an early form of the Italian Mafia and were notorious for bombings and kidnappings. At first, they had preyed largely on their own countrymen, but by 1911, as their confidence in moving among the English-speaking community increased, they widened their zone of activity to include rich Jewish businessmen. Their mode of action was to send threatening letters to their wealthy victims—when they refused to pay up, mobsters would kidnap their children or blow up their properties. In 1911, there were seventy bombings in New York City credited to the Black Hand gangsters. Sometimes the victims fought back.

  On August 14, 1911, the whole Italian community of the Lower East Side was celebrating the feast day of Saint Rocco. Four Black Hand assassins threaded their way through the crowds on East Eleventh Street to enter the grocery store belonging to the Calandro brothers—they had persistently refused their letters of blackmail and were now going to pay the price. But Sylvestro and Antonio Calandro recognized the gangsters through the shopwindow and pulled out pistols as soon they entered the store. Shots rang out and the four mobsters ran out into the street, causing panic as bullets flew everywhere. One gangster fell mortally wounded just outside the grocery store. A crowd gathered around him and called for a priest, but as soon they recognized him as a Black Hander, the mood changed. “Beware of La Mano Nera!” one shouted, and the crowd disappeared, leaving the man to die alone on the sidewalk. The Calandros were tried and acquitted for his murder.

  Two years later, Black Hand mobsters turned to poisoning the horses needed for delivering goods. When Jewish blacksmith Louis Blumenthal still refused to pay up, gangsters drove a car that cost them $3,400—all raised from frightened local businessmen—to his street, where they shot him dead. His murder roused all the other traders to get together and work with the police to run down the murderers. They succeeded, but they faced another major problem. “The immunity of the gangster from arrest has been due to the fear of the victims to appear against him,” said Eighth District Assemblyman Solomon Sufrin. “The only way to prevent the development of gangs in future will be found in giving more attention to the growing boy in the streets.”

  One of these growing boys was Salvatore Lucania, and he keenly followed the news of all the latest gang outrages. At the age of fourteen, he acquired his first gun. As he was showing it proudly to a friend, it went off and the bullet grazed his left leg. It gave him a scar he would bear for the rest of his life—the only time he would ever be shot. When his father found the gun, Antonio pointed it at his son and said he should shoot him for bringing disgrace on their family.

  “So I stopped coming home, when he was around,” Lucania later recalled. “I’d sleep in empty apartments in the neighborhood, or in pool halls. I’d only go home in the daytime, to get a hot meal from my mother. But I stayed away from my old man as much as I could.”

  His friends out on the street were his family, and it was them—not his brothers or his parents—who would help him get on in the world. When he got some money, he shared a furnished flat on East Fourteenth Street with two other men, one of them another wannabe gangster called Joe Biondo.

  Working as a delivery boy for the Jewish hatmaker Goodman helped shield Lucania’s criminal activities, but all the time he was building up his name as a gang leader with a following of violent kids who would do anything for money. Lucania and his mates would steal old-fashioned pocket watches and gold chains from wealthier Italian immigrants. He said he averaged a haul of three items a day. Early on, he was aware of the market in illicit drugs—especially heroin and cocaine—and started running errands for a local drug dealer. One day he delivered a vial of heroin to a prostitute in a bar who turned out to be a police informer, and he got caught. On June 27, 1916, at the age of eighteen, Salvatore Lucania was sentenced to eight months in prison at New Hampton Farms Reformatory.

  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 polic
e 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.

  3

  UPTOWN GAMBLER

  To 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.