Americans have always had a love-hate relationships with outlaws, from the folk heroes of the Old West to the Mafiosi of the 20th century and beyond. Jesse James was the subject of dime novels depicting him as a heroic figure long before he was killed by Bob Ford. Wyatt Earp was well acquainted with both sides of the law. The roving criminal gangs of the depression years became national figures, with some openly rooting for them to elude the lawmen who pursued them throughout the Midwest. Bonnie and Clyde were romanticized despite the spree of murders they carried out, some simply brutal executions of lawmen.
Following the 1930s organized crime became less actions by small roving bands, and more of a business ruled by bosses notorious for their ruthlessness. Individual thugs such as Dillinger, Baby Face Nelson, and the aforementioned Bonnie and Clyde were replaced by criminals who were less likely to be killers themselves, but more than willing to order murder done. Robbing banks was replaced with robbing citizens through loan-sharking, confidence games, gambling, drugs, prostitution, and the corruption of businesses and labor unions. Gangster wars in which criminals killed each other replaced the gunfights between policemen and criminals, and lawyers became the nemesis for the gangsters. Here are 10 of the most notorious gangsters in American history.
10. Arnold Rothstein was the first to run organized crime as a business
His fellow gangsters were so impressed with the mental acuity of Arnold Rothstein that he was nicknamed “the Brain.” Rothstein emerged from the Jewish mob in New York before Prohibition, and was widely suspected of fixing sports events in order to profit from gambling on them. Boxing matches, baseball, horse racing, dog racing, and other events were manipulated by Rothstein through a network of criminals whom he employed full-time, as well as enforcers to whom he turned when it was perceived that disciplinary measures were called for. It was Rothstein who most likely arranged the fixed World Series involving the Black Sox in 1919, though neither the fix nor his involvement has ever been proved.
Rothstein was one of the first to exploit Prohibition through bootlegging, and the organization he built for the purpose included many of the more famous underworld names of the period. Legs Diamond, Dutch Schultz, Meyer Lansky and Charles Luciano, later known as Lucky, were all part of his criminal enterprises. He became the arbiter of disputes between various gangs, and his decisions were respected as final. Rothstein was killed when he refused to pay a debt he incurred from a poker game which he alleged was rigged. He refused to identify the gunman as he lay dying, telling the police that they should stick to their business and he would stick to his. The breakup of his criminal empire led to many of the gang wars of the 1930s.
9. Al Capone used the widespread corruption of Chicago’s government to build his empire
The original Scarface rose, if that is the word, from the tough New York City gangs of Five Points to become a bouncer in mob controlled brothels in that city before moving to Chicago as a personal bodyguard to gangster and bootlegger Johnny Torrio. A gang war between the city’s North and South side gangs led to Torrio being almost killed. Wisely choosing retirement, Torrio handed his control of the South side to Capone, who ruthlessly expanded his operations, becoming the leading supplier of illegal booze in Chicago, as well as seizing control of illegal rackets, brothels, and a large segment of the city government. At the same time Capone harbored the goodwill of many citizens, through soup kitchens, offers of employment, and other activities which brought him the reputation of a new Robin Hood.
Capone flaunted his wealth with expensive suits, jewelry, cars, women, and food. He purchased entire trains of sleeping cars to carry himself and his entourage to Florida vacations, though his increasing paranoia led him to doubt all but his closest associates. How many murders can be lain at his feet is debated, though his guilt in ordering and planning the famed St. Valentine’s Day Massacre is well established. Whether he once beat three former associates to death with a baseball bat is debated by scholars, though such an act was certainly within character for the gangster. Capone died from syphilis after serving a term in federal custody for tax evasion, but the criminal empire he founded – known as The Outfit – continues to operate in Chicago to this day.
8. Charles Luciano created the modern criminal organization known colloquially as the Mob
Charles “Lucky” Luciano was another tough street punk who was mentored by Arnold Rothstein, along with his fellow gangsters Vito Genovese, Joe Masseria, Frank Costello, and others in the criminal pantheon of the 1930s. Besides teaching Luciano the rudiments of operating a crime syndicate featuring bootlegged liquor, brothels, and the numbers rackets, Rothstein taught his young charge how to scour off the marks of the street hood and become accepted in polite society. Luciano became as comfortable ordering dinner at New York’s finest restaurants as he was buying a hot dog at Nathan’s. By the mid-1920s Luciano was one of Joe Masseria’s most trusted aides. Luciano returned that trust by having Masseria killed, with one of the gunmen a thug by the name of Benjamin “Bugsy” Siegel.
It was not Luciano who first organized the Five Families of the Cosa Nostra as is widely believed. Salvatore Marranzano deserves that bow, and after placing Luciano at the head of one of the five families, Luciano had him killed. Luciano then reorganized the Five Families, setting up the Commission to resolve disputes without violence. After many years of investigations federal prosecutors led by Thomas E. Dewey finally convicted Luciano on charges of pandering in 1936. From federal prison he continued to control organized crime in New York and New Jersey. In 1942 he entered into a secret agreement with the US government to ensure the docks of New York and New Jersey remained in operation, and he used his Sicilian mob contacts to obtain information beneficial to the Allies during the invasions of Sicily and Italy. He was deported to Sicily after the war, relocated to Havana, thence back to Italy, where he continued to control organized crime for many years, until his death in Naples in 1962.
7. Dutch Schultz was one of Luciano’s greatest competitors in New York
Born Arthur Simon Flegenheimer, the gangster took the more manageable name of Dutch Schultz while rising to power in New York’s Jewish gangs of the 1920s. Schultz’s criminal career began when he started robbing craps games on the streets of New York. The name Schultz came from his brief period as a driver for Schultz Trucking Company. By the mid-1920s, Schultz was working as a bouncer and enforcer for establishments owned by associates of the Italian gangs in New York. In 1928, Arnold Rothstein was shot and eventually died from his wounds; it was widely believed that Schultz, by then a powerful New York bootlegger, had ordered the hit as retaliation for a fatal attack on his partner, Joey Noe. No one was ever convicted for Rothstein’s murder.
Schultz committed several murders himself, one of which was of Jules Modgilewsky, known as Julie Martin. Schultz killed Martin by shooting him in the mouth, before witnesses to whom he apologized for killing someone in front of them. After having his operations crippled by aggressive prosecutions by Thomas Dewey, Schultz appealed to the Commission for permission to kill Dewey. Denied, he ordered a hit on Dewey anyway, which failed. Luciano, desirous of taking over Schultz’s operations, used the disobedience as an excuse to have Schultz eliminated. In October, 1935, Schultz was shot by gunmen working for Murder Inc. A legend soon arose that Schultz had secreted over $7 million in cash and bonds in a safe buried in the Catskills. The safe, if there was one, has never been found.
6. John Dillinger was the king of the roving gangs of the 1930s
The Depression Era featured roving gangs of outlaws who crisscrossed the Midwest robbing banks and stores, engaging in violent and spectacular shootouts with local law enforcement. The gangsters included names which became legendary: Bonnie and Clyde, Baby Face Nelson, Pretty Boy Floyd, Machine Gun Kelly, and the king of them all, John Dillinger. Dillinger was involved in spectacular jail breakouts, robberies which were marked by shootouts with the criminals armed with submachine guns and automatic rifles, car chases, ambushes, and frequent disappearances. He attempted to alter his appearance through plastic surgery, sent taunting letters to police and newspapers, and became enamored by the public after his stated goal of not stealing from the common man, but from the banks who robbed the people.
Dillinger and his gang, of which there were several variations, robbed two dozen banks over the course of less than one year, during which they also robbed police stations and armories in search of weapons, as well as stores and gas stations. Stealing a car was a commonplace occurrence for the gang. During the year of violence Dillinger was charged with but one homicide, though members of the gang committed several others. It was the pursuit of Dillinger which led the small US Bureau of Investigation to grow into the Federal Bureau of Investigation. Killed by law enforcement after he was betrayed by a brothel owner hoping to avoid deportation, Dillinger became a legend in life which grew after his violent death. He has been portrayed in film numerous times since, with Warren Oates, Robert Conrad, Mark Harmon, and Johnny Depp, among several others, adding their interpretation of his life to his myth.
5. Frank Costello was called the Prime Minister of the Underworld
Born in Italy, and growing up in New York’s East Harlem neighborhood where his father operated a small store, Costello began his criminal career at the age of thirteen – or at least that was his age when he first drew the attention of the police. Another of the criminal students of Arnold Rothstein, Costello joined a gang which included Bugsy Siegel, Meyer Lansky, and Vito Genovese and which committed robberies, extortion, loan sharking, bookmaking, and the sale of narcotics. When Prohibition began their contacts and their strong arm tactics were useful to Rothstein and the bootlegging networks which emerged during the so-called Great Experiment. Costello managed to survive the organized crime wars of the late 1930s (Castellammarese War) and emerged as a leading associate, the consigliere, of Lucky Luciano.
Luciano appointed Genovese as the head of the family when the former went to prison, and when the latter fled to Sicily to avoid prosecution on a murder charge in 1937, Costello became the boss. Throughout the 1940s Costello grew the family’s illegal activities and brought in huge profits, including from operating fixed horse races in California through his associate Bugsy Siegel. In the 1950s Costello became nationally famous when he testified before the televised Kefauver Committee hearings which gave the public a glimpse into the underworld. Costello survived several prosecutions, for tax evasion and contempt of Congress, and an assassination attempt by Genovese in 1956. He retired the following year and maintained a residence in the Waldorf Astoria until his death in 1973.
4. Bugsy Siegel and the birth of Las Vegas as a gambling mecca
Bugsy Siegel is often depicted as a victim of the mob, angered by his failure to generate immediate profits from his new casino, paid for with Mafia money. Siegel was in fact one of the New York mob’s most violent and ruthless hitmen, who helped found the notorious killing machine Murder Incorporated. A boyhood friend of Al Capone, Siegel became well known for his abilities with knives, guns, and the garrote, and his willingness to use them for both pay and his personal satisfaction. His prowess as a hitman put his own life in danger, and in 1933 Siegel made the first of what became several trips to California, eventually settling there in the late 1930s with the intent of extending East Coast criminal enterprises to the West Coast. Siegel used strong arm backing from New York to take over Los Angeles’s numbers and bookmaking activities.
Siegel hobnobbed with Hollywood royalty in California, becoming somewhat of a celebrity himself as he appeared in public with the likes of Gary Cooper, Clark Gable, Cary Grant, and a variety of starlets. In the 1940s he began construction of the Flamingo in Las Vegas, using mob money and promising huge profits when the casino opened. They failed to appear as promised. At the same time Siegel skimmed profits from the other mob operations on the West Coast he was responsible for, diverting the money into the Flamingo and into his own pockets. By late winter 1947, the Flamingo, after opening, closing, and reopening to great publicity, was delivering a small profit, but the mob bosses were tired of waiting. Siegel was killed by long range rifle shots while in the home of his girlfriend, Virginia Hill, on June 20, 1947. The triggerman who killed the former hitman was never identified.
3. Johnny Roselli was recruited by the CIA in the early 1960s
Johnny Roselli’s criminal career began in the Chicago of Al Capone while Capone was still working as a bodyguard for Terrio. Born Fillippo Sacco, Roselli insinuated himself into the film industry in California, and was later heavily involved in extortion activities against Hollywood producers. By the 1940s he was well known as an enforcer for the Chicago Outfit. It was Roselli who, under orders from The Outfit, ordered Columbia Pictures’ Harry Cohn to offer a contract to a young and unknown actress who had caught the eye of Outfit boss Tony Accardo. Cohn, under pressure from Roselli, complied. The name of the young actress was Marilyn Monroe.
In the 1960s Roselli was involved with CIA attempts to kill Fidel Castro in Cuba. He was a known associate of Frank Sinatra, who sponsored Roselli’s membership in the Friars Club, where Roselli was soon involved in cheating at cards in a widespread scam. In the 1970s Roselli was linked to an alleged conspiracy in the murder of John F. Kennedy, as well as to the disappearance of Jimmy Hoffa. Roselli testified to the House Committee investigating the Kennedy assassination in 1975, days before Sam Giancana was scheduled to testify. Giancana was shot and killed before he could appear. In 1976 Roselli was called before the committee to testify a second time, but Roselli could not be found. In August 1976 his dismembered body was discovered in a steel barrel floating near Miami in Dumfounding Bay. Who killed him has yet to be determined.
2. Whitey Bulger enjoyed the protection of the FBI as he committed multiple murders
Few thugs in American history were as remorseless and ruthless as James Joseph Bulger Jr. Bulger hated the nickname Whitey, preferring to be called Jimmy. He was eventually indicted for 19 murders based on the eyewitness testimony of associates, though he probably killed several more. He supported IRA terrorists with both money and weapons, operated loan sharking, bookmaking, narcotics rings, and other criminal activities, all while serving as an informant for the FBI. He gave the FBI information regarding the operations of the Italian Mafia in South Boston, in exchange for which the FBI looked the other way regarding Bulger’s activities. Eventually FBI agent John Connolly tipped Bulger about his pending arrest, giving the murderer and extortionist time to flee.
Bulger evaded justice for more than a decade, during which time he was second only to Osama Bin Laden on the list of Ten Most Wanted Fugitives. Throughout his criminal career Bulger had stashed funds and false identity documents which helped him in his flight. Captured in 2013, he was convicted of more than thirty felonies, including being involved in 11 murders. He was sentenced to two life terms plus ten years, and transferred from one federal prison to another before being sent to Hazelton, a high-security federal prison in the mountains of West Virginia, known to its residents as Misery Mountain. Within a few hours of his arrival Whitey Bulger was beaten to death by inmates who used a heavy padlock secured in a sock as their weapon. His eyes were nearly gouged out and his tongue cut through, organized crime signs of the victim having been an informant.
1. Leroy Nicky Barnes created an African American mob in Harlem
Nicky Barnes was a small time drug dealer and heroin addict in Harlem when he was sent to prison in 1965. While incarcerated he beat his own addiction and met Joey Gallo, a member of the Colombo family. Whether Barnes learned the advantages of organizing his criminal activities along corporate lines from Gallo or not is uncertain, but when Barnes was released he returned to Harlem with a business model in his head. In 1972 Barnes formed a seven man organization he named The Council, along the model of the Mafia, to more efficiently run narcotics distribution in New York. Eventually his operations moved into Pennsylvania and across the border into Canada, as with the Mafia including legitimate businesses to launder money and to mask illegal activities.
Barnes was arrested numerous times, evading convictions through bribery and extortion, and earning the sobriquet Mr. Untouchable. Eventually he was convicted through the federal courts and imprisoned for life without the possibility of parole. Imprisoned, he arranged a deal with prosecutors through which he provided evidence against other members of The Council, as well as other illegal activities. Barnes’s information led to the conviction of 16 drug traffickers, the indictment of another 28, and implicated himself in eight drug related murders. Barnes was released from federal custody in 1998 and entered the Federal Witness Protection Program. He has been featured in films including American Gangster in 2007, in which he was portrayed by Cuba Gooding Jr.