Top 10 Real-Life Mob Bosses

In the largest FBI Mob bust in history, 110 Mafia members were arrested and 127 charged across three U.S. states and Italy this week.

Some of the crimes, including murder and racketeering, took place 30 years ago in a different era for organized crime.

TIME takes a look at history’s most infamous mob bosses

POSTED IN ‘TIME’ / Thursday, Jan. 20, 2011

Semion Mogilevich

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One of the FBI’s 10 most wanted fugitives, Semion Mogilevich cuts a frightening figure. Called the “Brainy Don” (he has an economics degree), the Ukrainian-born mobster’s gang has a multinational reach, with his hands allegedly in everything from a Pennsylvania-based company that defrauded investors of $150 million to the East European gas trade. His other reputed crimes include murders, arms dealing and drug trafficking. Mogilevich was arrested in Moscow in 2008 for tax evasion, but, brainy and crafty as he is, was released the following year.


Al Capone

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You can’t have a list of mobsters without mentioning the man who sticks in the minds of most people: Al Capone. It seemed for years as if law enforcement couldn’t touch him. As head of the Chicago-based Italian-American empire known as the Outfit, Capone was guilty of any number of sins, from gambling and prostitution to bootlegging and narcotics trafficking to robbery, bribery and murder. Though his record is long, Capone gained the most notoriety for the infamous St. Valentine’s Day Massacre in which seven high-ranking members of a rival gang were shot dead. Though Capone himself had arranged to conveniently be vacationing at the time, there was little doubt the job didn’t have the boss’s approval. But what finally brought the mobster down was one of his most minor offenses: tax evasion. The lesser crime — and lighter sentence it carried — meant one of the most notorious crooks of all time served just seven years, six months and 15 days behind bars.


Charles ‘Lucky’ Luciano

New York Times Co. / Getty Images

Charles “Lucky” Luciano organized organized crime. The New York City boss built the now legendary Mafia model, turning petty criminal activity into a smoothly operating enterprise that turned serious profits. Along with his associate Meyer Lansky, Luciano even instituted a board of directors. The Genovese family crime boss set up shop in the Lower East Side and palled around with the likes of Frank Sinatra until U.S. special prosecutor Thomas Dewey charged Luciano with 62 counts of compulsory prosecution. He was deported to Italy in 1946 and then appeared in Cuba a year later. But he never regained the status and cachet his former life of crime had afforded him and died in 1962.


Pablo Escobar

Reuters / Corbis

As a teenager, Pablo Escobar would steal tombstones and sell them to smugglers in Panama. From those devious roots, he entered the coca business in the 1970s, just as the U.S.’s obsession with the highly addictive drug began. Thanks to his ruthless ambition, Escobar built up Colombia’s now infamous Medellin cartel into a powerful drug-trafficking enterprise that by the 1980s controlled more than 80% of cocaine shipped to the U.S., making him one of the 10 richest people in the world. After his death (he was gunned down at age 44 while on the run), books and movies shed light on just how lucrative his empire was. His son Juan Pablo Escobar (who changed his name to Sebastian Marroquin) said his father once burned some $2 million to keep himself and his daughter warm while they were on the lam. Another tale said Escobar once offered to pay off his country’s $10 billion national debt. But his reign was not just lucrative: Escobar was also one of history’s most violent criminals. The deaths of three Colombian presidential candidates, an attorney general, a Justice Minister, more than 200 judges, dozens of journalists, more than 1,000 police and countless ordinary citizens are all attributed to his rule.


John Gotti

DMI / TIME-LIFE Pictures

He is widely considered the last of the Hollywood-style mobsters, a man who could waltz into court dressed to the nines and waltz back out, acquitted. “Dapper Don” was named boss of the Gambino crime family in the mid-1980s, and soon became known as “Teflon Don” for his ability to avoid prison. Charges, people said, just wouldn’t stick. That was until the FBI embarked on a crusade to get John Gotti behind bars on numerous charges, including racketeering and murder. He was eventually sentenced to life in prison in 1992 and remained in jail until his death from cancer a decade later.


Hisayuki Machii

The Korean-born mobster got his start in the Japanese underworld after settling in Tokyo following World War II. Hisayuki Machii became a regular fixture in the black market and made his name in everything from tourism and prostitution to oil importing. He founded the Tosei-kai gang, which reached its height in the 1960s. The organization allowed Machii to become an essential fixer between Japan and South Korea. His exploits eventually made it possible for him to acquire a ferry service that connected Japan and South Korea along the shortest distance between the two countries. The gang was later disbanded, but Machii followed that up by forming two front organizations, Toa Yuai Jigyo Kumiai and Toa Sogo Kigyo. Machii retired in the 1980s, virtually unscathed by the law, and died in 2002.


Tony ‘Big Tuna’ Accardo

Francis Miller / TIME-LIFE Pictures

Tony “Big Tuna” Accardo died — remarkably, of natural causes — at age 86 in 1992. The “reputed” mob boss (he denied holding the position and eluded prosecutors) headed Chicago’s Outfit after Al Capone, and upon Accardo’s death the director of the Chicago Crime Commission said it was “the end of an era.” Accardo may very well have been a gunman in the 1929 St. Valentine’s Day Massacre, and he was on Chicago’s public-enemy list in 1931. But that was just the beginning of a long, dark career. For decades, he controlled the Outfit, and despite numerous arrests for activities ranging from murder and kidnapping to extortion, union racketeering and gambling, he never served any jail time. A 1960 conviction on tax evasion was overturned on appeal: the Big Tuna (apparently, he once caught a tuna weighing 400 lb., or 180 kg) was slick. He was also aggressive: another of his nicknames, “Joe Batters,” alluded to his handling of a baseball bat — and not for the game.


Salvatore Riina

Origlia Franco / Corbis

“Gentleman, you are making a big mistake,” is what Sicilian mobster Salvatore Riina told police when he was apprehended in January 1993 for his dark deeds over more than 20 years as a fugitive and operative in the Sicilian Mafia. He was wanted for his connection to more than 100 killings perpetrated during his climb to the top of the organized-crime gang. Riina, also known as “Toto,” was said to have started his career as a hit man. He went into hiding in 1969 after being acquitted of triple homicide. But that didn’t stop him from allegedly orchestrating the bloody Mafia wars in 1980s Sicily, which claimed dozens of lives and sealed his post at the top of the organization. In October 1993, despite his attempt to claim a case of mistaken identity, Riina was sentenced to life in prison, the harshest punishment allowed in Italy.


Dawood Ibrahim


Mustachioed and portly, it’s hard to imagine that Dawood Ibrahim is one of the most dangerous people in the world. Long heralded as the don of the Mumbai underworld, the shadowy Ibrahim went from being a classic extortionist huckster and gold smuggler in the Indian seaside metropolis to a man now implicated in a ring of global terrorist networks that include ties to al-Qaeda. Ibrahim is suspected as a potential suspect in masterminding a 1993 terror attack in Mumbai, which killed hundreds, and may have had a hand in the 2008 attacks on a number of prominent, ritzy Mumbai hotels. What adds to his mystique is that his whereabouts remain unknown — Indian intelligence officials suspect he is in Pakistan, possibly in the port city of Karachi, but the Pakistanis reject those claims. Some estimates of his wealth number into billions of dollars, tracing him to assets and properties from Malaysia to East Africa. In 2008, Forbes ranked him among the top 10 most wanted fugitives; the following year, Ibrahim made the magazine’s list of the world’s most powerful people.


Xie Caiping

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You’ve heard of the Godfathers — meet the Godmother. In Chongqing, a Chinese megacity with a population near 30 million, Xie Caiping held sway as a local kingpin (or queenpin) for a number of years. A Beijing crackdown on Chongqing’s entrenched mafia in 2009 revealed how Xie, for years, ran illegal gambling deals while keeping a string of local police and government officials in her pocket. She owned numerous luxury cars and villas and boasted a harem of some 16 young male paramours. Xie, 46, who looks more the part of middle-aged matron than criminal femme fatale, was eventually sentenced to 18 years in prison, but not before tales of her power and excesses titillated the regional media.


Top 10 Real-Life Mob Bosses / CREDIT : TIME / Thursday, Jan. 20, 2011


The Boss of All Bosses

The arrest last week of Salvatore Lo Piccolo was a triumph for Italian law enforcement: the second Capo dei Capi, or boss of bosses, of the Cosa Nostra, the Sicilian Mafia, to fall in as many years. But each leader — captured or at large — adds to the mystique of the still deadly 150-year old organization.

It continues to lord over life in Sicily, and do business with criminals across the globe. All too often, the symbiosis between Mafia legend and reality only adds to the difficulty in trying to dismantle it. Looking through the biographies of its top bosses, it is important to know the folklore, but to stay focused on the facts that matter. Here are snapshots of some of the Mafia’s notorious leaders from the past two decades.

Salvatore Lo Piccolo

Captured: Nov. 5, 2007

Salvatore Lo Piccolo

FOLKLORE: At the moment of their arrest on November 5, Lo Piccolo’s son Sandro shouted out to his father: “I love you, papá . I love you papá!” This kind of public family drama no doubt echoed some of the dialogue from the HBO series The Sopranos. But the intrigue increased a few days later when police confirmed that they had found a one-page document they believe the Palermo boss had written for would-be mobsters to avoid trouble. Among the so-called Ten Commandments: Do not covet the wife of your fellow mobster; and do not steal from other Mafiosi. Not on the list: “Thou Shall Not Kill”.

UGLY TRUTH: The Lo Piccolos are both convicted murderers. Police believe in the months before their arrest, the pair were successfully consolidating their power in and around the Sicilian capital, both by intimidation and by stepping up collaboration with American mobsters in the drug trafficking business.


Bernardo Provenzano

Captured: April 11, 2006

Bernardo Provenzano

FOLKLORE: His record 43 years as a fugitive turned this reticent boss into a kind of wiseman of the wise guys. His ability to evade authorities, who’d organized the greatest manhunt in Cosa Nostra history, was legendary as he cut off contact with his family and moved constantly from one safe house to the next in the Sicilian countryside. He was able to run the Mafia empire with the use of pizzini, tiny typed notes that were delivered by hand by his trusted lieutenants. The deeply Catholic Provenzano possessed five bibles found when he was nabbed; one copy was filled with cryptic notes and underlining that some believe are a code to many of the Mafia’s oldest, darkest secrets.

UGLY TRUTH: Though known as the man who brought a “pax Mafiosa” to the organization after a particularly bloody period, Provenzano rose through the ranks with a reputation as cold-blooded killer. Ultimately, though, the most chilling part of his legacy was an ability to impose a peace on his Mafia underlings. For Cosa Nostra is at its most potent when it is quietly going about its work in the rackets while infiltrating the above-board economy.


Giovanni Brusca

Captured: May 20, 1996

Giovanni Brusca

FOLKLORE: Known as “The Pig” for his unkempt appearance and huge appetites, including a thirst for blood. He once testified that he’d killed “between 100 and 200″ people with his own hands.

UGLY TRUTH: The actual details of his murders make the point that his round numbers don’t. Brusca killed the 11-year-old son of a rival boss who’d turned state’s evidence, dissolving the body in a vat of acid. His most devastating moment came in 1992 when he pressed the button that triggered the explosives under a Sicilian highway that killed crusading magistrate Giovanni Falcone, Falcone’s wife and five bodyguards.


Toto Riina

Captured: January 15, 1993

Toto Riina in 1993


FOLKLORE: The most cinematic moment in his 15-year reign as boss of bosses was a kiss that never happened. A turncoat witness testified that Riina had greeted the former Italian Prime Minister Giulio Andreotti with a “kiss of honor” at a meeting in the early 1980s to discuss the outcomes of a major Mafia trial.

UGLY TRUTH: While commanding Cosa Nostra from the mid 1970s to early 1990s, Riina waged a bloody war on both internal rivals, and the Italian state. He also made sure to nurture important political connections in Sicily, though Andreotti is unlikely to have been one of them. The former prime minister has spent years in and out of court battling charges of Mafia links, connections he has consistently denied.




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