17 Most Infamous Mob Bosses of All Time

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17 Most Infamous Mob Bosses of All Time

Who are the most infamous mob bosses of all time? Organized crime has always been a captivating subject for the American public. At the head of any of these organizations is a boss, someone who guides actions both good and bad from the shadows.

Al Capone

infamous mob bosses
Capone comes to mind immediately when talking about the mafia.

When it comes to infamous mob bosses, you can’t top Al Capone. That man was a rum runner, murderer, and head of one of the most powerful crime families in Chicago during the 1920s and 1930s.

Crime Doesn’t Pay, but the IRS Expects You To

infamous mob bosses
Tax evasion was the main charge they caught Capone on.

Capone was done in by the IRS, oddly enough. The Feds got one of the most infamous mob bosses of all time on tax evasion charges. It worked though, and it kept Capone out of power. He would eventually die shortly after his release from prison in 1947.

Semion Mogilevich

infamous mob bosses
Mogilevich is still at large.

Many of the most infamous mob bosses are figures from the past. Semion Mogilevich is still alive and well, which isn’t a good thing. He is on the FBI Most Wanted List for a good reason after all.

A Massive Bounty

infamous mob bosses
If you have the gumption, you could net a handsome reward for Mogilevich’s arrest.

Mogilevich has evaded custody for years now, despite multiple criminal charges being brought against him. Anyone who aids in his arrest can expect to receive the $5 million reward. That seems a bit dicey to me, so I’ll just be happy leaving it well enough alone.

Shigeharu Shirai

A strong man wearing sunglasses.
Shigeharu’s pretensions of being a legitimate businessman didn’t last long.

Japan’s organized crime factions don’t get nearly as much press as you’d think. That said, the Yakuza has its share of infamous mob bosses. Shigeharu Shirai was the leader of the Yamaguchi-gumi, one of the more powerful clans in Japan.

Caught Because of Social Media

cropped shot of yakuza member with tanto knife
Distinctive tattoos can be a double-edged sword.

In a fun twist, Shigeharu ended up extradited to Japan due to his distinctive tattoos. A Thay local snapped a picture of his ornate tattoos and Shigeharu was back in Japan where he was eventually convicted of murder.

Matteo Messina Denaro

Matt Denaro
Denaro spent years on the run, evading capture for decades.

Many organized crime families have ties to Europe. Matteo Messina Denaro is one of the most infamous mob bosses of the 20th century and operated primarily out of Sicily. However, Denaro has far more power to wield than many American organizations.

A Life on the Run

infamous mob bosses
The law finally caught up to Denaro last year, where he died in prison.

Despite all of his power, Denaro has spent most of his life on the run. A 2002 life sentence has yet to be served, with Denaro never staying in the same place for too long. He was finally captured in January of 2023, where he subsequently died in custody.

Matthew Madonna

Glass of champagne and game masks on table at party
Madonna got to enjoy the opulence and excess of the Lucchese mob.

Few crime families have the same level of infamy as the Lucchese mob. With roots dating back to the 1930s, it is a marvel that has lasted this far into the modern day. For Matty Madonna, he took power in 2008.

A Modern Mobster

Matthew Madonna
Madonna has been in prison since 2020.

The 9 years of power Madonna held saw the Lucchese grow to new heights not seen since the Great Depression. Crime doesn’t pay, as we’ll find out time and time again. Madonna is serving a life sentence for murder as of 2020.

Charles Luciano

infamous mob bosses
Luciano was already a major player at the turn of the 20th century.

Charles “Lucky” Luciano likely doesn’t need much of an introduction. He’s one of the most infamous mob bosses for good reason. Surprisingly, he was already in a position of power before the First World War.

Pride Before the Fall

infamous mob bosses
Luciano spent plenty of time behind bars.

Luciano’s nickname came from his immense skill as a gambler. With a name like that, it does go to your head after a while. Luciano died an old man but spent decades in prison for his crimes.

Meyer Lansky

meyer lansky
Lansky was known for both his slick manner of speaking and his vicious streak.

When you talk about infamous mob bosses, you have to mention Meyer Lansky. Lansky doesn’t fit the mold of the Italian mafioso but had a vicious and interesting career nonetheless.

The Mob’s Accountant

Meyer Lansky
Lansky enjoyed the high life until 1970.

Lansky was good at making money, a skill he exploited when moving into skimming casinos in the 1940s. Eventually, that luck ran out when he was arrested in 1970. He died an old man, which seems rare for someone in his career path.

Carlo Gambino

Carlo Gambino
Gambino was in and out of prison since his youth.

Gambino is rumored to be the inspiration behind Mario Puzo’s “The Godfather” which is about the only real accolade you can give one of the most infamous mob bosses. A violent and sly man, Gambino had a career spanning more than 40 years in Italy and the United States.

Never Captured

Gambino Crime Family
Gambino was the head of one of the biggest crime families in the United States.

Despite the many charges and crimes the man committed, Gambino never served much time behind bars. Gambino was a free man, living his days in leisure until his 1976 death.

Vito Genovese

Vito Genovese
Genovese helped consolidate power to the Five Families.

Genovese is arguably one of the most powerful men on this entire list. He has certainly earned his spot on the most infamous mob bosses list thanks to his help in forming the Five Families. Genovese was right there alongside Lucky Luciano in consolidating power in the 1930s and 40s.

A Sentence Left Unserved

Vito Genovese
His rise to power was short-lived, Genovese died in prison.

Genovese was a brash and impulsive man, using violence to gain massive leaps in power. That came to an end in 1959, when Genovese was sentenced to 15 years for drug trafficking charges. He died in 1969.

Frank Costello

Frank Costello
Costello testified before Congress about his activities.

Not many of the infamous mob bosses on this list can boast of being shot in the head and living. Frank Costello of the Five Families of New York gets that dubious honor. He’s best known for a calm and collected image, but that fell apart in the 1950s.

Death by Natural Causes

Frank Costello
Costello ended up shot in the head and got out while the getting was good.

Costello essentially retired after a failed hit in the 1950s. He survived but moved out of the limelight and out of power. Costello died of natural causes in 1973, still holding on to some of the casinos he helped bring into the fold.

John Gotti

John gotti
Other mobsters hated Gotti’s brazen and bold personality.

Gotti is arguably one of the most infamous mob bosses of the 20th century. The 1980s were a decade of glitz, excess, and opulence. They were a perfect time for someone like John Gotti to come to power.

The Teflon Don

John Gotti
Charges stuck to Gotti, making that nickname a poor fit.

Gotti was quickly dubbed the Teflon Don for his ability to evade capture. Which would’ve worked in his favor if it weren’t for his eventual capture and conviction in the 1990s. The Teflon Don spent the rest of his life in prison, dying of cancer in 2002.

Joe Bonanno

Cigar and the mafia around
Bonanno shows some of these mobsters how it’s done.

There is something to be said about an earnest criminal I suppose. Joe Bonanno is another one of the infamous mob bosses linked to the Five Families but for very different reasons. He only got arrested for the first time in 1980 as an old man.

Bonanno Tells All

Joesph Bonanno
A tell-all book isn’t what you usually hear about when discussing the mob.

Three years after his prison stint, Bonanno wrote a tell-all book about his time in the mafia. It broke many major taboos of the internal codes the families abide by, but it makes for a fascinating look at how such an organized crime family works. Bonanno died at 97 years old in 2002.

Joe Colombo

Mafia man in suit counting money on black background.
Legit fronts and criminal activities, a match made in mobster heaven.

Some of the most infamous mob bosses latch on to novel causes to further criminal aims. The 1960s saw Civil Rights at an all-time high on the lips and minds of the average American citizen. Col0mbo was able to leverage that into posing as the head of an organization meant to aid Italian-Americans.

A Civil Rights Fraud

Silhouette of a man in a coat and hat in a dark alley on a rainy night. theme of violence and cruelty. blur effect
An assassination attempt took Colombo out of the running.

Joe Colombo was a slick-talking huckster, who was able to finagle people like Frank Sinatra into playing benefit concerts. His career came to an abrupt end when he was shot in the head in 1971. He survived the assassination attempt but ended up paralyzed and comatose. He died in 1978.

Albert Anastasia

infamous mob bosses
Anastasia was a vicious man who met a vicious end.

Few men soaked themselves in blood like Albert Anastasia. He is one of many infamous mob bosses to come to power during the Great Depression, but he lived a life led by gunplay and murder.

A Life of Violence

infamous mob bosses
Jack O’Halloran claims Anastasia is biological father, which is a strange claim to make.

Anastasia evaded capture for most of his career. Witnesses would end up murdered or they simply refused to testify. 1957 saw Anastasia meet his end via assassination, a fitting end to a louse of a man.

Vincent Gigante

infamous mob bosses
Gigante preferred shuffling around and mumbling to more overt signs of activity.

I suppose something is interesting about infamous mob bosses who embrace eccentric behavior. Vincent Gigante operated in the shadows for decades following his entry into the mob.

Faked Madness

vincent gigante
Once he admitted to faking insanity, the charges piled up against Gigante.

Gigante faked being a mumbling madman with no real power for decades. The ruse was up in 1997 when real concrete charges started being filed against him. Gigante fessed up and ended up dying in prison in 2005.

Tony Accardo

Tony Accardo
Accardo filled the vacuum left by Capone.

Tony Accardo only had legitimate employment as a boy. After that, he served years of his life in various gangs before ending up as a trusted lieutenant of Al Capone. If Capone was the brains, Accardo was the muscle, especially after his part in the St. Valentine’s Day Massacre.

Capone’s Successor

Frank 'The Enforcer' Nitti was a first cousin of Al Capone. In March 1943 he was indicted with several other Mafioso from Chicago and New Jersey for extorting $2,500,000 from the motion picture indust
Frank Nitti helped aid Accardo’s rise to power.

Capone’s arrest and death left a power vacuum in Chicago. Accardo was able to snap up territory and power for himself, something he held on to for decades. He died of natural causes in 1992.

James Bulger

infamous mob bosses
Bulger was in an out of jail his whole life, even volunteering to test LSD to reduce his sentence.

James “Whitey” Bulger is perhaps best known as one of the infamous mob bosses that inspired Martin Scorsese’s “The Departed.” However, there is much more to the man than meets the eye. Bulger served multiple sentences for crimes but eventually became an informant to reduce his sentence.

Violent Ends

whitey bulger
Bulger’s final fate is as ghastly as the crimes he committed while free, a fitting end.

Bulger’s status as an FBI informant kept him shielded for years until 1994. Bulger went on the run, eventually getting arrested in 2011. He died an old man, but it wasn’t peaceful by any means. The mob boss would meet a violent end at the age of 89.

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