#1 Lucky Luciano
Even though he may not have been as rich as Al Capone and a few others, no mobster in American history was more influential than Charles “Lucky” Luciano. (pictured above) All of the top mobsters in New York in the 1920’s and 1930’s took their ultimate orders from Lucky. He was a ruthless killer who also possessed a ton of ambition and business sense that gave him an edge in every situation.
He was the creator of two very important groups, The National Crime Syndicate and The Commission. The Syndicate was a ruling body for mob families all over the country and it included Jewish and Irish mob bosses. This was the first time in America that crime family leaders would agree to actually sit down together and mediate business matters.
Lucky decided that the major five families in New York City needed the same kind of ruling board and that led to the creation of the Commission. These organizations elevated the mafia from a group of warring street gangs to a sophisticated society with a hierarchy and rules. It was Lucky Luciano who turned the mafia into a legitimate power in America.
Related Story: Charles “Lucky” Luciano: A Criminal Genius
#2 Al Capone
He was the first mobster to make millions and build an empire based on bootlegging. Capone made more money than any gangster before or in the years since. He had absolute control over liquor distribution. When it comes to movies and entertainment, the name Al “Scarface” Capone is the most commonly portrayed mobster. He was played by Robert DeNiro in the blockbuster movie, The Untouchables.
Capone set a high standard from mob boss brutality. He wouldn’t hesitate to kill a law enforcement agent or a politician. He was known for beating several people to death with baseball bats. Al Capone may have been the most power hungry and ruthless mafia boss in history. In the notorious St. Valentine’s Day massacre, he had seven of his enemies killed at one time.
Scarface was able to pay off jurors and kill witnesses for years, but would eventually be taken down by a tax evasion case. He got syphilis and began to wilt away in prison, a mere skeleton of what he used to be. He died on January 25, 1947. The empire that he built known as the Chicago Outfit would carry on without him and continue to prosper for many decades after his death
#3 Meyer Lansky
Meyer Lansky was the most powerful Jewish gangster that ever lived. He was someone that Lucky Luciano had genuine trust and admiration for. Meyer was his chief shot caller for National Crime Syndicate operations. Some Italians were jealous of the royal treatment that Lansky received but Luciano would not hear such complaints.
Meyer had a legendary cast of Jewish mobsters that fell in line under his command. You had Benjamin “Bugsy” Siegel, his partner in the “Bugs and Meyer Gang”. Then there was the Murder Inc. boss Lepke Buchalter. At this time, the Jewish mob was fully on par with the Italian mafia in New York and around the country.
He set up gambling empires all over the world and may have been the richest gangster since Al Capone. Although Jewish, he had more authority in the mafia than anyone except Lucky Luciano. Meyer invested heavily in his offshore operations and kept a lower profile in his later years. Lansky passed away from lung cancer on January 15, 1983.
#4 Carlo Gambino
Carlo Gambino led a very charmed life for a mafia boss. While he was feared, it was the respect he had among his peers that led him to become the boss of bosses. He could have people killed with a simple nod or a wink. From 1957-1976, he was the most powerful mobster in America and the New York mafia had one of its’ most prosperous eras as a result.
It was Carlo who masterminded the killing of Albert Anastasia in 1957 with the help of Vito Genovese. Carlo was much more popular than Anastasia with the other bosses, he was diplomatic in comparison. He was even respectful to the FBI agents who were constantly surveilling him and showing up at his door. He was a true wolf in sheeps’ clothing.
By the mid 1970’s, the legendary don was in ailing health. He had avoided the authorities and his enemies for his entire career and now the end was near. This was when most people felt that he made his biggest miscalculation in naming Paul Castellano as next boss of the family. Everyone knows what happened over the next decade.
#5 Vito Genovese
One word you could use to describe Vito Genovese is ambitious. He was determined to take over the remains of the Luciano Crime Family and make it his own. However, shortly after he was named acting boss in 1936 he was forced to flee the country and go back to Italy. Frank Costello would step into his place while Vito vowed that he would one day come back to take his rightful spot.
Vito was extradited back to the United States in 1945 to face murder charges. After all of the witnesses in the case were killed off, there was no one left and the charges were dismissed. He was back in New York and ready to claim his prize, with the help of a young hitman named Vincent “The Chin” Gigante. After Chin shot Costello in 1957, Costello agreed to concede power to Genovese.
That wasn’t the only coup that Vito was involved in. He also teamed up with Carlo Gambino and Meyer Lansky to kill the most feared mobster of that generation, Albert Anastasia. Vito would screw up ordering the Apalachin meeting and end up back in prison shortly after. He achieved the goal that he set out for originally, the Luciano family will now forever be known as the Genovese family.
#6 Frank Costello
He was nicknamed “The Prime Minister of the Underworld” for his vast political influence. He took over the Luciano family in 1937 when acting boss Vito Genovese fled the country. Luciano had been convicted in the prostition ring the year previously, and now he fully got behind Frank Costello.
Costello was one of the most popular bosses around because he didn’t make excessive financial demands of his soldiers and captains. Like future Gambino boss Paul Castellano, Costello owned a poultry business and many other legitimate adventures. When the Kefauver Hearings took place in 1950, Frank Costello was announced as the boss of bosses.
Costello had a solid alliance with Albert Anastasia and with his backing, Albert was able to become the boss of his own family. 1957 was a bad year for both men. First Costello was shot by a young Chin Gigante in May, the Anastasia was famously shot to death a few months later. Costello survived and decided to take his millions and retire in peace.
#7 John Gotti
His run at the top was brief but very eventful and it left a permanent impression on the mafia and its’ culture. His run as a boss only last 5 years before he went to prison for life but he continued to rule the family through his son and brother Pete. The Gotti family controlled the Gambino Crime Family from 1985-2010, unfortunately their earnings are a fraction of what they were in the 1980’s.
Gotti was unlike any other boss in that he loved the camera, and was a natural in front of it. He embraced the publicity and that went against what La Cosa Nostra stood for. He had fun with the attention. When a reporter asked him if he was the head of the Gambino family, with a slight grin Gotti explained that he was the boss of his own family, his wife and kids at home.
Gotti had a cult like following but also some fierce rivals, like Chin Gigante. He survived a few plots on his life including the one where his underboss Frank DeCicco was blown up. He had the three trial victories which led to him being dubbed “The Teflon Don”. Many of his former underlings are still active today keeping his street legacy going while his celebrity factor is etched in stone.
Related Story: Timeline Of John Gotti
#8 Joe Bonanno
Known as “Joe Bananas”, Joe Bonanno ran his crime family for three decades. He got his start in the mafia in Salvatore Maranzano’s bootlegging operations. He was known to be streetwise with crossover skills in business management and organization. After the Castellammarese War, Bonanno emerged as one of the five New York bosses and a member of the Commission.
Bonanno became one of the richest bosses in New York. He was able to operate with little distraction for most of his career because the Bonannos were very good at flying under the radar. He built up an empire that included countless legitimate legal businesses. Joe Bananas did not flaunt his wealth, choosing modest homes and cars so as not to gain unnecessary attention.
After his family broke out in its’ first civil war in the 1960’s, he was forced to go into hiding. He would be forced by the Commission to retire which he did in 1968. Bonanno ticked off the other bosses when he released his own book, which acknowledged the existence of the Commission. The Bonanno family still bears his name nearly a century after he became boss.
#9 Joe Colombo
He wasn’t just a mafia boss, Joe Colombo was a very effective activist. He organized the Italian American Civil Rights League, an organization that held some massive rallies where Colombo would speak. While most of his peers agreed with his activism, they were unhappy with the unnecessary attention it created. They wanted to remain in the shadows.
Colombo had a friendship and partnership with Carlo Gambino which made him one of the Commission elites. He was trying to manage a family known for inner turmoil, the Colombos have had many civil wars over the years. His biggest problem in the family was a renegade soldier named “Crazy Joe” Gallo, who desperately sought to take over the family.
On June 28, 1971, Colombo was coming to the podium to speak in front of many thousands of Italians at his rally. One of Crazy Joe’s disciples approached and suddenly shot Colombo, who would survive but become an invalid. Joe Gallo was gunned down the next year, Colombo died in 1978. The family he once ruled still bears his name today.
#10 Albert Anastasia
He was the one and only “Lord High Executioner”, Albert Anastasia was the most feared mafia boss ever and one of its’ most hated. Albert was an original disciple of Lucky Luciano and rode his coattails to the top of the New York mafia. He sat on both the National Crime Syndicate and the Commission. He and Lepke Buchalter led the infamous hit squad, Murder Inc.
Albert was the longtime underboss in the Mangano family before finally getting bored with that position and killing Mangano in 1951. It wasn’t the first mafia boss that he killed. He killed Joe Masseria way back in 1931. When a murder needed to be committed, Albert Anastasia was the man to get it done. He made that his living for over three decades and was the best in the business.
The problem for Anastasia was that he was too reckless. The Mangano hit was unsanctioned and he also killed a public figure named Arnold Schuster in 1952. His fellow Commission members starting to fear for their own safety began to plot Anastasia’s demise. He was gunned down in 1957 in his barber’s chair. The shot of Anastasia’s murder scene may be the most famous mafia picture ever.
Related Story: Albert Anastasia: The Lord High Executioner
#11 Vincent Gigante
Vincent “The Chin” Gigante will forever be remembered for his bizarre public behavior. While he did indeed suffer from mild mental illness, he played it up and it was a true sight to see. Chin had beaten a case back in the 1960’s by way of insanity, so he was staying ready for a repeat. He would walk clumsily down the street looking half conscious.
He was so good at the deception that he was able to convince authorities that another man, Fat Tony Salerno was boss of the Genovese family for years. When the FBI indictments from the Commission case came out, they announced Fat Tony as boss. While this was going on, he spent years plotting the murder of John Gotti, which he never got done.
He was the young gangster who in 1957 shot Frank Costello on orders of Vito Genovese. Although botching that hit, he quickly ascended the Genovese ranks to become boss after Vito went to prison. Eventually, the FBI would catch up with “The Oddfather” in 1997 and his hoax was exposed when he admitted to it in court.
#12 Tony Accardo
Very few mobsters had the longevity that “The Big Tuna” Tony Accardo enjoyed over his 65+ years in the Chicago Outfit. He got his start all the way back under Al Capone. Accardo was the boss and filled various positions through the years. During his early years, he was often referred to as “Joe Batters” over stories that he killed a few men with a baseball bat. Accardo allegedly participated in the St. Valentine’s Day Massacre by his own admission.
After Capone went to prison, Accardo’s position in the Outfit continued to rise. He had a diverse set of money making rackets that included loansharking, bookmaking, extortion and gambling. He created many outlets to make money and was named boss in 1943. Over the next 30-50 years, he sometimes took lower titles like consigliere while still having ultimate control.
His low key lifestyle kept him out of the press and kept law enforcement off his back. He presided over several generations in the Outfit. By the 1980’s, he had semi retired to Florida where he lived out the rest of his days. Having only spent one single day in jail in his entire life, the low key Accardo died from a heart condition on May 22, 1992 at 86 years old.
#13 Whitey Bulger
James “Whitey” Bulger was one of just a handful of mobsters to make it to the FBI’s 10 Most Wanted List. For years he was number two and then when Osama Bin Laden was killed in 2009, Bulger took the top spot and stayed there until 2011. During his years on the run, he became almost a mythical figure in the underworld.
Whitey was the leader of the very violent Winter Hill Gang which controlled organized crime in Boston. What makes Bulger so important is how he was able to attain power, by using the FBI to prop him up. He was a lower level guy but after knowing the FBI would look the other way, he got absolutely ruthless in his quest for power.
After being arrested in California, Bulger was sent back to Boston to face charges for 19 murders. He eventually received multiple life sentences in 2013. Karma would catch up to Whitey on October 30, 2018 when he was brutally beaten to death after being released into general population by his request. He was 89 years old and bound to a wheelchair at the time.
#14 Raymond Patriarca Sr.
He wasn’t as well known as the New York bosses but Raymond Patriarca was the undisputed leader of the New England mafia for over three decades. Like many of the other bosses, he rose up in the prohibition era and diversified his rackets to stay relevant in later years. Patriarca was an expert extortionist and demanded a piece of everything in New England.
Patriarca kept his base in Providence, Rhode Island but most of his rackets were in Boston. His power only grew when during the McLean/McGlaughlin war of the 1960’s killed off most of his Irish competitors as he watched from the sidelines. All illegal and many legal businesses were forced to pay kickbacks to the Patriarca family as a price of existing on their turf.
The FBI finally caught up with Patriarca in 1970 and he was convicted of a murder. He spent the last years of his life in prison and died of cardiac arrest on July 11, 1984. After his son took over the family, things began to go downhill. The younger Patriarca didn’t possess what his father had, culminating with him being recorded by the FBI in a making ceremony.
#15 Carmine Persico
While he may have been seen as a bit of an outcast to the bosses of the other families, Carmine “The Snake” Persico didn’t care. He was able to keep a virtual stranglehold on power as boss of the Colombo family for four decades. There were no shortage of contenders trying to take Persico’s crown and nothing he wouldn’t do to keep it.
As a young man, he teamed with “Crazy Joe” Gallo to kill Albert Anastasia. Later on, the two would become enemies and Persico would have Gallo killed. Carmine became Colombo boss in the early 1970’s. He was in control of the most violent and conflicted family in New York but Persico was always. He would become one of the longest reigning mafia bosses in American history.
Despite all the years of wars and betrayal, Persico was able to retain command. The Snake passed away on March 7, 2019 at 85 years old after having been in prison since the 1980’s. The family is much smaller in size now and only time will tell if they continue to be a significant presence anymore.
#16 Paul Castellano
During his time as boss from 1976-1985, he had a massive stable of killers and big earners in the family. He had Nino Gaggi and Roy DeMeo’s crew handling most of the contracted hits. Then there was the crews led by John Gotti, Sammy Gravano, Joe “Piney” Armone and Franki DeCicco. Big Paul at one time had all of these crews and more earning money for him and doing his enforcement on command.
What Paul had that helped him excel was great connections being Carlo Gambino’s cousin. He had earnings from legitimate businesses like his poultry company which he invested in his criminal ventures. As a boss he gained massive wealth but his soldiers felt like he demanded a little too much. During his reign, the Gambinos remained the top family in New York.
Castellano will forever be remembered as the somewhat aloof Gambino boss that John Gotti killed in 1985. There’s also the affair with the Colombian maid and penis implant sagas. Then there was the fact that all of his underlings knew that it was underboss Neil Dellacroce and not him that deserved the job after Carlo Gambino died. The last couple years of his life were not kind to “Big Paul”.
#17 Lepke Buchalter
Louis “Lepke” Buchalter was the only mob boss in history to be executed in the United States. He was put in the infamous electric chair in Sing Sing prison known as “Old Sparky”. Lepke had been the co-leader of Murder Inc. alongside Albert Anastasia. He had a spot on the board with Luciano’s Syndicate.
What made Lepke unique at the time was being one of the very first union racketeers and a powerful one. He and his partner Jacob “Gurrah” Shapiro took full control of the garment industry rackets when they killed their boss Jacob “Little Augie” Orgen in 1927. They soon were raking in millions per year and found plenty of competition which needed to be eliminated.
Although a soft spoken and courteous man in appearance, Buchalter orchestrated hundreds of killings with Murder Inc. His luck ran out after Abe Reles became a government witness. Lepke was executed on March 4, 1944, just minutes after his two Murder Inc. hitmen Mendy Weiss and Louis Capone took their turns. Lepke declined to make any last comments.
Related Story: The Only Mafia Boss To Be Executed
#18 Toto D’Aquila
Salvatore “Toto” D’Aquila was a captain in the very first American mafia family, the Morello Gang. This was in the very beginning of the 20th century and the Morellos were lead by Guiseppe “Clutch Hand” Morello. D’Aquila quickly outgrew his capo position and wanted to be a boss, which required him to break free and leave the Morellos. A war ensued but the Morellos fell on hard times.
Toto had the most powerful crew in the family with active young talent like Frank Scalise and Manfredi Mineo. This was the crew that would one day become the Gambino family. Carlo himself came to the United States in 1921 and quickly became a respected member of the D’Aquila family. We were now in the era of bootlegging and bigger profits.
With the increased profits came much more violence competing for the spoils. Toto was set up and murdered in 1928 by Mineo, who took over and was killed in 1930. The boss became Frank Scalise until Luciano demoted and replaced him with Vincent Mangano just a year later. Mangano stayed boss until his murder in 1951 by Albert Anastasia, who then was killed and replaced by Carlo Gambino in 1957.