Cigar Aficionado

Most of what we think we know about organized crime comes from the movies—actors in pinstriped suits and Borsalino fedoras who made us offers we couldn’t refuse. Some of it comes from historians who have conducted questionable interviews of anonymous gangsters willing to talk about “the life” in unverifiable tales that mix fact and fiction. The most reliable information was probably generated from the tedious legwork of FBI investigations.

What we’ve come to know with certainty is that the rules of organized crime are quite simple: you’re either an asset or you’re a liability. If you’re deemed a moneymaker, you stick around and work your way up the criminal ladder until you rise so far above the rackets that very little illegal activity can be traced back directly to you. That is, assuming you live long enough. But if it’s been decided that you’re a liability—or even a minor threat—then you’re terminated, murdered with pathological indifference. Everyone from the dimmest street soldier to the shrewdest crime boss knows this, if not intellectually, then certainly on instinct. 

The rackets of organized crime range from low-level, local operations—prostitution, illegal gambling and loansharking—to large scale, international enterprise like narcotics or human trafficking. In America, over the last century and a half, most of the players in this corrupt arena we call the Mafia end up in jail or eliminated before ever attaining any kind of notoriety. But a few, by way of ruthlessness and intelligence, have made their way to the more dubious pages of history. 

It would be a mistake to celebrate their achievements or be seduced by the swagger of these notorious figures. Ultimately, this is a list of criminals who have used the tools of terrorism to prosper and live an existence of violence and paranoia. But writing about organized crime is not tantamount to glamorizing it, as is often the accusation. It’s simply a question of the historical record. 

What we’ve assembled here is a list of players who have had the largest impact on American organized crime. They represent the clannish subculture of criminality that was imported mostly from Sicily and Americanized over subsequent generations—a deranged version of the American Dream. These are men whose nefarious actions have left their mark on society. They changed the look of Las Vegas, turned Cuba into a gambler’s paradise and earned (and spent) fortunes. They have been accused of all manner of crimes—even the killing of a president. Now that the strict code of silence known as omerta has long been broken, their achievements have become a matter of public record and are every bit as fascinating as they are frightening. —Gregory Mottola

1. Albert Anastasia (1902-1957)

For a man who came to Mob prominence as a contract killer and head of Murder Inc., Albert Anastasia managed to escape the law on a fairly regular basis. His slipperiness, however, didn’t save him from the long arm of gangland justice.

Born Umberto Anastasio in Calabria, Italy, he snuck into New York at age 17 and became a longshoreman. He went to prison for stabbing a coworker, but his violent skills came to the attention of one Lucky Luciano who got him an appeal. Witnesses conveniently disappeared or turned up dead before the retrial—a trend that would continue throughout his career.

Anastasia (along with Vito Genovese, Joe Adonis and Bugsy Siegel) is thought to have capped Joe “The Boss” Masseria in 1931, consolidating Luciano’s power. His reward was being named underboss to Vincent Mangano, who ran the waterfront. At the time, Anastasia was rising in Murder Inc., gangland’s enforcement arm, which arranged as many as 1,000 assassinations. He also struck a deal with the government to protect the docks from espionage during World War II. Mangano’s resentment of his underling’s increased importance only grew, and then Mangano mysteriously disappeared in 1951, drawing the ire of other New York families, who suspected Anastasia was to blame.

While Anastasia’s own murder couldn’t have been more public—he was shot in the barbershop of a Manhattan hotel in 1957—no one was ever arrested for the crime. It is supposed that Genovese and Carlo Gambino orchestrated the hit as the latter assumed control of Anastasia’s Mob family. Joey Gallo, who bragged of being one of the assailants, met his own very public end in Umberto’s Clam Bar in Little Italy 15 years later. ­—Jack Bettridge

2. Rosario “Russell” Bufalino (1903-1994)

That you probably never heard the name Russell Bufalino before watching Joe Pesci play him in The Irishman is a testament to the low profile he maintained. The head of the northeastern Pennsylvania crime syndicate became one of America’s most influential mobsters and built a fortune estimated by some at $1 billion. Rumored as one of the dons who ordered the killing of Jimmy Hoffa, Bufalino has also been tied to the John F. Kennedy assassination and attempted hits on Fidel Castro. 

Sicilian born, Bufalino came to the U.S. at an early age and was a criminal by the time he was a teen. He married into a Mafia family and rose to prominence, eventually running northeastern Pennsylvania with connections far and wide. His criminal interests included gambling, loansharking and racketeering, although he also boasted considerable legitimate businesses such as real estate. He stayed in the shadows until the Valachi hearings of 1963, when he was called “one of the most powerful and dangerous leaders of the Mafia.”

He testified at the Pennsylvania Crime Commission in 1982. In his light-colored suit and conservative tie, he looked like the CEO of a Fortune 500 company until he raised his left hand to his ear and revealed a missing part of a thumb and finger, rumored to have been blasted off by a shotgun.

Bufalino wasn’t big, but his threats loomed large. When he threatened to strangle a man he was imprisoned for extortion; when he tried to have the informant killed, he was brought up on murder charges. Unlike in The Irishman, Bufalino made it out of his cell, and stayed active in the Mafia until his death at the age of 90. —David Savona

3. Al Capone (1899-1947)

No mobster wielded more power in the days of Prohibition than Chicago boss Al Capone, who seldom spared the tommy gun. “You can get much further with a kind word and a gun,” he once said, “than you can with a kind word alone.”

Violence came easy and early to Capone, who was born in Brooklyn at the turn of the 20th century to parents who emigrated from Naples, Italy. After striking a teacher at age 14, he dropped out of school and joined a succession of New York street gangs, including the James Street Boys. He earned his nickname “Scarface” after being slashed across his left cheek. By 21 he had committed his first murder. In 1919, he was invited to Chicago to become a Mob enforcer.

Capone’s violence only escalated in the Windy City, usually for the purpose of protecting his most lucrative interest: bootlegging. Murder was a common method of eliminating competition. He is believed to have ordered what became known as the Saint Valentine’s Day Massacre. On February 14, 1929, mobsters dressed as policemen took out seven members of the rival North Side Gang in a blizzard of machine and shotgun fire. (The one victim who was still alive when the police arrived had 14 shots in him, but refused to divulge any details. He died soon after.) Capone spent only seven years as boss, but amassed a fortune estimated at $100 million, worth some $1.5 billion today. Despite all the bloodshed in his wake, it was tax evasion that finally took him down. He was sentenced to 11 years in Alcatraz in 1932 at the age of 33. Wracked by syphilis, he was paroled in 1939, and died in 1947. —David Savona

4. Frank Costello (1891-1973)

More than any other American mobster, Frank Costello (born Francesco Castiglia in Calabria, Italy) attained the image of a legitimate CEO. As a young man, he partnered with Lucky Luciano, Meyer Lansky, Owney Madden and other underworld pioneers to become one of the Founding Fathers of the New York Mob, but Costello eschewed violence. His great skill was negotiating sensible, lucrative partnerships with mobsters of all ethnicities—Sicilian, Jewish or Irish. He had a large role in establishing links between the underworld and Tammany Hall, the political machine that elected mayors, governors and presidents. In 1932, when gangsters were shooting it out in the streets of New York, Costello was in Chicago at the nomination of Franklin Roosevelt at the Democratic National Convention. 

After Luciano was convicted in 1936, Costello became acting boss of the Five Families. When served with a subpoena to testify at the Kefauver hearings in 1951, Costello balked at showing his face on live television. His lawyers negotiated an arrangement to hide his face, so the cameras focused on his hands as he testified. The effect was somehow more sinister, the result a TV sensation. Marlon Brando later said that he based the voice of Vito Corleone on Costello’s.

On May 2, 1957, with Costello out on appeal after a tax evasion conviction, his primary rival, Vito Genovese, sensed an opening. Genovese contracted 29-year-old hitman Vincent “The Chin” Gigante to take out the boss. Costello survived the hit attempt, but his standing was weakened. He turned over power to Genovese and retired from the Mob living in Manhattan as a kind of éminence grise of the underworld, until he died of natural causes in 1973. —T.J. English

5. Sam Giancana (1908-1975)

Where but in America could a poor kid from the slums grow up to shape international events? For Sam “Momo” Giancana, no neighborhood, federal organization or presidential office was off limits. Fidel Castro murder attempts, CIA scandals galore and the assassination of JFK—Giancana may have had a hand in it all.

Raised by Sicilian immigrants, Giancana grew up on the West Side of Chicago and by 17 had chalked up a rap sheet for auto theft. He set his sights on being a “triggerman” for the 42 Gang, a band of teenage toughs who aspired to Mob status, and by age 20 was suspected in three murders. Soon, he made the big leagues—the infamous Chicago Outfit—and Momo aimed high. After a stretch at Leavenworth, he strong-armed his way to a takeover of the illegal lottery racket. He was on his way, and throughout the 1940s and 1950s ran most of the Outfit’s illegal gambling, bootlegging and political racketeering across the country.

When Giancana expanded to Panama and Iran, he smuggled weapons to Israel’s Mossad with the CIA, which later allegedly recruited him to assassinate Fidel Castro, a spectacular failure. Nevertheless, he was rubbing shoulders—and sharing mistresses—with the likes of Frank Sinatra and John F. Kennedy. Giancana is rumored to have secured Kennedy’s victory in Illinois in the 1960 election. Things went thorny when Kennedy’s attorney general brother Bobby turned his sights on the Mob. Momo’s own daughter would later claim the betrayal pushed Giancana to order the president’s death in 1963. Involved or not, the gangster was gunned down cooking sausage and peppers just before he was supposed to testify against the CIA. —Chris Esposito

6. Vincent Gigante (1928-2005)

It was all handshakes and pats on the back for the feds when they busted the Five Families in 1986, but the joke may have been on them. Each surveillance task force focused on a specific family, and when the federal agents finally nailed “Fat Tony” Salerno on racketeering, there was no doubt that they captured the head of the Genovese crime family. Meanwhile nobody gave much thought to Vinnie “The Chin” Gigante—the “Oddfather,” the “Enigma in the Bathrobe”—and why should they? He seemed to be mentally deteriorating as he shuffled through the streets of Greenwich Village in his pajamas, muttering to himself, swatting at invisible foes and urinating in public. 

In his youth, Gigante hadn’t been much more than muscle for the Mob. His biggest claim to fame had been shooting crime boss Frank Costello in 1957—and he hadn’t even done that right. Costello survived. Then Gigante put on a paranoid performance so convincing that he was officially diagnosed with schizophrenia. In the guise of the doddering village idiot, Gigante functioned as the acting boss of the Genovese family starting in 1981 with Salerno propped up as the front boss. The charade allowed Gigante to extort garbage, trucking and construction operations, as well as tamper with labor agreements.

Ultimately, the feds would revisit the Genovese crime family investigation and further surveillance showed that Gigante was more than just a nutty imbecile off his meds. In 1990, he was indicted for extortion and bid rigging. In ’93 he was indicted again, this time for sanctioning murder (including a hit on John Gotti). Despite appearing in court in bathrobe and pajamas, Gigante was deemed able to stand trial when Sammy “The Bull” Gravano testified he was faking. In ’97, Gigante got a 12-year sentence, and died in prison in 2005. —Gregory Mottola

7. Enoch Johnson (1883-1968)

The Atlantic City political boss Enoch Johnson may have been the model for the character Nucky Thompson in the cable series “Boardwalk Empire,” but the real-life Nucky was more interesting for his subtlety than the lurid portrayal we saw on TV. Machinations, not muscle, gave him power. Indeed, Johnson was never known to have killed or even ordered an assassination. As a sheriff’s son and a WASP who controlled a Republican enclave in a largely Democratic state, he didn’t fit the gangster stereotype. His many political hats made him a kingmaker who filled offices as lofty as U.S. senator.  

By the time of Prohibition, his family was already offering political protection to vice providers (gambling and prostitution) in the seaside resort. Nucky extended the service to bootleggers and speakeasies. Rather than participating, Johnson took a cut on every drop of alcohol that flowed freely in Atlantic City. Unapologetic about the arrangement, he said about the vices: “If the majority of the people didn’t want them they wouldn’t be profitable and they would not exist.” To make the beach town a year-around destination he built a state-of-the-art convention center. The system not only benefitted business, but voters were rewarded as Johnson threw lavish parties and made sure no one went hungry at Thanksgiving. 

In the end, it wasn’t his open association with mobsters that brought Nucky down. The story goes that he ran afoul of William Randolph Hearst by lavishing attention on a showgirl that the media magnate was wooing. Hearst launched a newspaper attack that ended in a tax evasion rap and Nucky traded his trademark boutonnieres for prison stripes for four years. Released in 1945, he would only dabble in politics until his death from natural causes at 85 in 1968. —Jack Bettridge

8. John Gotti (1940-2002)

You’ve seen the smiling mug shots, the tailored suits, the defiant swagger. John Gotti took the unusual—for a wiseguy—tack of nurturing a high-profile persona. This dark prince was dubbed The Dapper Don for his fine Italian suits and the Teflon Don for his ability to evade conviction. 

An operative of the Gambino crime family, Gotti burst to public attention in 1985 for orchestrating the murder of his boss Paul “Big Paulie” Castellano. The Gambino faction was an enormous enterprise that, according to the FBI, grossed nearly $500 million a year and included everything from gambling and loansharking to racketeering and narcotics. What made the Castellano hit noteworthy was that it wasn’t sanctioned by the Five Families, a governing board of directors that presided over all of New York’s Mafia activity. 

Gotti not only avoided Mob revenge, but skated on a number of legal charges: assault in 1986; racketeering in 1987; and assault charges in 1990 after he was arrested for shooting a corrupt labor union official. All of his trials were heavily covered by the media and every Gotti victory only served to boost his popularity. The FBI was not amused. 

Eventually, after aggressive surveillance, the feds found a cooperating witness in Salvatore Gravano. Sammy “the Bull” (or “the Rat,” depending on how you look at it) was an underboss who spilled his guts. Gotti was convicted in 1992 of a slew of racketeering charges and five counts of murder, including that of Castellano. He was sentenced to life in prison and died at 61 years old at Marion Penitentiary in Illinois. Organized crime has yet to see such a cult of personality since the time of Gotti—and that’s exactly how they prefer it. —Gregory Mottola

9. Meyer Lansky (1902-1983)

His name may be different, but of all the big-screen portrayals of gangsters, the character Hyman Roth from The Godfather: Part II is one of the most faithful to real life. Meyer Lansky may not have literally sliced a Cuba-shaped cake at his birthday party, but he did oversee the transformation of Havana into a gambler’s paradise. And, like in the movie, he actually said, “We’re bigger than United States Steel.”

Born Meier Suchowlanski, a Polish Jew in what was then the Russian Empire, he fled pogroms with his family to emigrate to New York City’s Lower East Side. As a boy, he showed cerebral, even-tempered qualities that set him apart on the mean streets. But he was never soft. As a youngster he stood up to Lucky Luciano, who had tried to shake him down for cash. His toughness impressed the future Mob kingpin, and Lansky and another cohort, Bugsy Siegel, became his long-time associates.

Lansky avoided publicity and (for the most part) prosecution. He was involved in bootlegging during Prohibition and segued into gambling, owning interests in casinos in Havana, Las Vegas, Florida, and New Orleans, as well as London. When the
Flamingo in Vegas became a money pit, underworld investors blamed Siegel, who was running it. Just as it played out on-screeen, Lansky was forced to agree to a hit on Bugsy, who is portrayed as Moe Green in The Godfather. The  mobster’s downfall is also accounted somewhat accurately: the Cuban revolution killed his interests in Havana, Lansky retreated to Florida and then sought asylum in Israel but was rejected. However he was arrested—not gunned down—upon his return to America. Acquitted on tax evasion, Lansky lived to see his onscreen portrayal.  —Jack Bettridge

10. Charles Luciano (1897-1962)

If anybody put the “organized” in “organized crime” it was enlightened Mob visionary Charles “Lucky” Luciano, who saw that bloodshed was bad for business and wholesale cooperation was key to bringing the Mob into the 20th century. His coordinated approach to management incorporated all the major crime syndicates nationwide in one body called The Commission. The first step was to extinguish the Castellammarese War, an ongoing, citywide battle between Salvatore Maranzano and Luciano’s own boss Giuseppe Masseria. 

Luciano turned on his own leader, conspiring with rival Maranzano to have Masseria iced. When Maranzano established the Five Families of New York City, he declared himself the capo di tutti capi—boss of all bosses—upsetting the balance Lucky dreamed of. He also conspired to kill Luciano. A short reign for Maranzano was the only answer.

With Maranzano dead, it was Luciano who, in 1931,  established The Commission, a Mafia board of directors that included representatives from New York, Buffalo, Philadelphia and Chicago. It controlled not only such rackets as gambling and prostitution, but allowed infiltration of legitimate entities like labor unions and construction. 

Luciano would eventually be taken down by New York City’s crusading prosecutor Thomas Dewey, convicted on 62 counts of forced prostitution. After 10 years in prison, his sentence was unexpectedly commuted when the Office of Naval Intelligence asked for his help during World War II. On Luciano’s orders, all dock workers on the Port of New York cooperated with the U.S. Navy. In return, Luciano was released from prison early and deported back to Italy in 1946, where he resumed criminal activity in narcotics until he died of a heart attack in 1962 at 64 years old, young by today’s standards, but in Mob years, that’s closer to a century for civilians. —Gregory Mottola

11. Giuseppe Masseria (1886-1931)

Before the Five Families, before The Commission and before the Mafia became organized, there was Giuseppe “Joe the Boss” Masseria, one of the last relics to rule New York’s criminal underworld in the old-school style of  Mafia monarchy and strict omerta.  

Masseria emigrated from Sicily in 1902, and before long he joined the Harlem-based Morello/Terranova gang, which dated back to the 1800s, when America’s Mafia was in its infancy. Even by the 1920s, the New York Mob was still a rough patchwork of gangs fighting for control of small-time rackets. A series of murders ended with Masseria becoming “boss of all bosses,” one of the last mobsters to possess such a title of absolute power.  

As head of the Morello crime family, Masseria became known as “Joe the Boss” with an ambitious Charles “Lucky” Luciano as one of his trusted lieutenants. True to his nickname, Masseria demanded heavy kickbacks from his underlings and squeezed smaller gangs to pay large tributes. His authority was challenged in 1930 by Salvatore Maranzano, a rival gangster from Castellammare del Golfo in Sicily. The Castellammarese War, a series of turf battles, lasted from February 1930 to April of 1931.

Luciano secretly switched sides and plotted with Maranzano in hopes of ending the war. As the story goes, an unsuspecting Masseria joined Luciano for a card game one afternoon at a restaurant in Coney Island. When Luciano excused himself to go to the men’s room, Masseria was shot to death by gunmen believed to include Bugsy Siegel, Albert Anastasia and Vito Genovese. With no official witnesses there were no convictions, just the next generation of gangsters waiting to take over, and a new style of leadership on the bloody horizon. —Gregory Mottola

12. Dutch Schultz (1902-1935)

Many mobsters garnered nicknames to suggest their questionable mental state (“Mad Dog” Coll, “Crazy” Joe Gallo, Vincent “The Oddfather” Gigante), but the one who was unstable enough to propose killing a U.S. Attorney was simply called “Dutch.”

Born Arthur Flegenheimer in the Bronx, Schultz took up his byname while working for the Schultz Trucking Co., with the moniker “Dutch” apparently a mispronounced reference to his German heritage (Deutsch). On the advent of Prohibition, the firm began bootlegging; Shultz left, and soon was making money via a ring of speakeasies with partner Joey Noe. 

Brutality was their answer to any competition. Wishing to expand into Manhattan, Schultz soon clashed with the bootlegger Jack “Legs” Diamond, a protégé of Arnold “the Brain” Rothstein, who supposedly fixed the 1919 World Series. Rothstein and Noe ended up dead. Diamond was shot, but recovered and sought new territory in Albany. The vengeful Dutchman, who was implicated in more than 100 murders, also rubbed out compatriots he felt had betrayed him.

When Prohibition ended, Schultz branched out into strong-arming restaurants and tried to muscle into the Harlem numbers racket, starting a bloody and protracted turf war with kingpin Bumpy Johnson. Schultz’s success made him a target of gangbuster prosecutor Thomas Dewey. Dogged by a series of tax evasion charges, Schultz asked the Mafia Commission for permission to have the future governor offed, but was refused. When Dutch threatened to act on his own, Lucky Luciano decided the underworld didn’t need the heat and ordered Schultz’s own execution. Hit men gunned him down in the restroom of a New Jersey chophouse. Police taped some 27 hours of his incoherent deathbed babblings in a vain attempt to determine his attackers. Schultz is said to have buried $7 million in profits somewhere in Upstate New York. Happy treasure hunting. —Jack Bettridge

13. Benjamin Siegel (1906-1947)

The handsome, charming, well-dressed but often volatile Benjamin “Bugsy” Siegel is best remembered for his contribution to sprucing up Las Vegas (although he did not live to enjoy the fruits of his labor). But to paint him as a mere real estate developer would be to sell him short.

Growing up in Williamsburg, Brooklyn, Siegel started in petty theft, graduated to extorting street peddlers and was soon a bootlegger and murderer. His association with Meyer Lanksy introduced him to Lucky Luciano, and Siegel is often linked to the hit on Giuseppe Masseria, a murder that consolidated the Mob Commission in New York City. He also palled with the founders of Murder Inc. for whom he is assumed to have moonlighted.

His unwelcome nickname “Bugsy” referenced his penchant for erratic violence, although he showed other quirks (like once trying to sell munitions to Mussolini). When his behavior made him too hot for New York, he moved to Los Angeles where he chummed not only with gangster Mickey Cohen, but a long list of Hollywood stars and an equally explosive mistress, Virginia Hill.

Together, the two planned Siegel’s path to legitimacy: the Flamingo Hotel and Casino on the Las Vegas Strip. He muscled in on the stalled project and then poured in Mob money, trying to make it the town’s most lavish development. Bugsy’s opulent vision came in five times over budget and the Flamingo struggled to turn a profit. His Mafia backers grumbled until the night he was taken off the project—via a hail of bullets. While Lansky is said to have tried to stave off Siegel’s murder, his own thugs invaded the Flamingo to take charge only hours after Siegel’s execution. —Jack Bettridge