Idiots Guide: 20th Century American Gangsters

If there was a ‘hey day’ for the American Gangster, then the 20th century was certainly it. Ironically, these gangsters have been turned into attractive anti-heroes in American pop culture. Their collective felonious exploits often being portrayed in films, and television throughout the 20th century, and beyond. The popularity of ‘Tony Soprano’ being a perfect example. The following list highlights some of the more notable, and in some cases, quite colorful underworld characters in American crime history. Watch your back as you scroll down. You never know who’s watching you!

#11. Mickey Cohen / Jewish Mafia / Penalty: 4 Years for Tax Evasion. Died free. (1976)

Mickey Cohen

Mickey Cohen was a serious Los Angeles based gangster and a high ranking member of the Jewish Mafia. He was also affiliated with the Italian American Mafia for the better part of three decades, well into the 1960’s. Early in his career, he ran gambling operations for Al Capone’s ‘Outfit’ in Chicago. In June of 1951 Cohen was convicted, and sentenced to 4 years in prison for tax evasion. Upon his release in 1955, he became something of a  celebrity, while running ‘legit’ business’s like floral shops, nightclubs, casinos, and even some gas stations. Then in 1961 Cohen was convicted of tax evasion for a second time, and sent to Alcatraz. He was eventually released from Atlanta Federal Prison in 1972, being diagnosed with stomach cancer.  Mickey Cohen died in his sleep in California, in 1976.

#10. John Dillinger / Bank Robber / Penalty: Killed by Police (1934)

John Dillinger 2

John Dillinger epitomized the term ‘balls’. This prolific depression era bank robber relieved over 25 banks of their cash, and he even raided police stations for weapons!  ‘Balls’ remember?  He also squeezed in the murder of about a half dozen people in Chicago, and Indiana. His brazen criminal exploits sold many a newspaper, and made him the most notorious,  of the legendarily notorious criminals, in American history. His head to head fight with, and evasion of, the FBI resulted in his shooting death outside a Chicago movie theatre in 1934. The police having been tipped off by his girlfriend.

#9. Frank Lucas / Narcotics King Pin / Penalty: 70 Years (1976) Only Served 11.


Frank Lucas is a legendarily successful former heroin kingpin. He operated in Harlem, NY during the late 1960s and early 1970s. His business started after his tour of Vietnam when he started getting his supply from the ‘Golden Triangle’ syndicate in Southeast Asia. He infamously used the caskets of slain soldiers to smuggle his heroin into the United States. At the height of the his success Lucas claimed to have made $1 Million per day. Wether this was true or not, what is not in dispute was his status as a serious gangster. The 2007 film ‘American Gangster’ based on his life and exploits were a testament to this. In 1975 Lucas was arrested, and later convicted of both state and federal drug charges. The following year he was sentenced to 70 years in prison, of which he served only 11.

#8. Benjamin ‘Bugsy’ Siegel / Murder, Inc. / Penalty: Murdered (1947) 


In many circles, Benjamin ‘Bugsy’ Siegal is considered the ‘father’ of Las Vegas. His obvious charm,  matinee idol good looks, and celebrity status belied the fact that he was one of the most feared gangsters of his day. Like his friend and associate, Meyer Lansky, Siegal was able to bridge and exploit both the Jewish mob, and the Italian mob. He was one of the founders of Murder, Inc. while being a prolific bootlegger during the Prohibition era. Acquitted of murder in 1942, Bugsy went west to Nevada, and was instrumental in forming the now famous Las Vegas ‘strip’. By financing the original casinos, among them the ‘Flamingo’, Siegal solidified his power base in Vegas. However, the Flamingo flamed out and Siegal’s power began to wane. He was eventually murdered in June of 1947 at his home in Beverly Hills, CA.

#7. Meyer Lansky / Crime Syndicate / Penalty: None. Died Lung Cancer (1983)

Meyer lansky

Sometimes an accountant can be very dangerous, and not just about your personal finances. Take Meyer Lansky for example, working as a Mafia accountant, he helped develop the National Crime Syndicate in the United States. He was very good with figures they say, and was instrumental in developing some of the largest gambling operations in the United States, maybe even the entire world over. At the time of his death in 1983 Lansky was one of the wealthiest men in the country.

#6. Sam ‘Momo’ Giancana / The Chicago Outfit / Penalty: Murdered (1975) 

Sam giancana

Sam Giancana was boss of the Chicago Outfit from 1957–1966. He was known for living a high profile life which was not very popular with his associates, he had a friendship with Frank Sinatra, and his relationship with star singer Phyllis McGuire, which brought undue attention wasn’t seen in a good light. Giancana’s antics became too high-profile for the Outfit tastes and federal scrutiny soon followed. As a result, Giancana was called before a grand jury in 1966, and his mandatory silence, landed him in prison for well over a year. Upon his release, Giancana moved to Mexico, where he was then arrested by Mexican authorities in 1974 and deported back to the United States. He came back to Chicago in July of 1974. A year later, he was found murdered in his home in July of 1975.

#5. Charles ‘Lucky’ LucianoGenovese Crime Family/ Penalty: 50 Years (1936)

Lucky Luciano

Lucky Luciano is widely considered the ‘father’ of modern organized crime in America. Being the man who was responsible for the organization, and creation of the 5 American Mafia families, he was also responsible for the first Mafia ‘Commission’. After being prosecuted and convicted for compulsory prostitution in 1936 and sentenced to 50 years in prison, Luciano was freed after agreeing to help the United States during World War 2. He was immediately deported back to Italy, where he died in 1962.

#4. Carlo Gambino / Gambino Crime Family / Penalty: Suspended Sentence (1937)

Carlo Gambino

Carlo Gambino had a reputation for being ‘low key’, and ‘secretive’, and in 1957 he became the figure head of the Commission of American Mafia. Carlo’s empire had criminal business interests in New York, Chicago, Los Angeles, Miami, Boston, San Francisco and Las Vegas. He was also instrumental in taking over the New York Longshoremen Union, controlling 90 per cent of New York City seaports. The family had an estimated 500 ‘soldiers’, comprised of 30 crews that generated in excess of $500 Million a year. Serious business. Carlo Gambino ran not only his family, but the other New York families with impunity, and successfully evaded publicity, and law enforcement pressures. He was convicted once in 1937 but that sentence was suspended. He died a free man in 1976.

#3. Alphonse ‘Scarface’ Capone / Chicago Outfit / Penalty: 11 Years Tax Evasion (1932)

Al capone

It’s likely that Al Capone‘s legendary temper developed from years of dedicating his life to smuggling liquor across borders and into speakeasies, and promoting prostitution. Amazingly, his 7 year run as Chicago Outfit mob boss engendered the kind of publicity that has generated books, movies, and a secure spot in American pop culture. He did all of this by the time he was 33 years old, then it was over. The Prohibition Era, and the bootleg trade that was a natural result of it, made many bad men very rich, Alphonse Capone was certainly no exception. Masterminding the infamous Saint Valentine’s Day Massacre hurt Capone’s image and made him a prized target of the feds. They caught up to him, not for the many murders, and mischief he raised, but tax evasion. In 1932 he was convicted, thus ending a short but eventful criminal career.

#2. James ‘Whitey’ Bulger / Winter Hill Gang / Penalty: 2 Life Terms & Five years (2013)


After being indicted by a federal Grand Jury for 19 murders, James ‘Whitey’ Bulger  went underground in December of 1994, and stayed on the lam for 16 years with his FBI insider links having been broken, and exposed. He was a spry 81 years old when finally apprehended in Santa Monica, CA in 2011. Ending a grotesque criminal career that started in 1975, and making him the latest member of the FBI’s ‘Most Wanted’ list to be captured. In June of 2013, Bulger went on trial for 32 separate criminal counts, including racketeering, money laundering, extortion, weapons charges, in addition to the original 19 murders. On August 12, 2013, he was found guilty on 31 of those counts and sentenced to 2 life terms and an additional five years in case the life terms weren’t sufficient. By all accounts, Bulger was a diabolical criminal with murderous intent.

#1. John Joseph Gotti  / Gambino Crime Family / Penalty: Life Without Parole (1992) 

John Gotti

Starting in the mid 1980’s John Gotti had risen to become among the most powerful crime bosses of the era. His dapper dress, and impeccable style garnered him the nickname ‘Dapper Don‘. He also gained another more sinister nickname, ‘Teflon Don‘ for his ability to beat state and federal charges time and again. Against traditional Mafia Don behavior, John was outspoken, generous, and flamboyant, which made him a star to average people on the streets of his neighborhood. The F.B.I. made him a high priority target, and were finally able to make a racketeering case,  five murders, conspiracy to commit murder, loansharking, illegal gambling, obstruction of justice, bribery, and tax evasion charges to ‘stick’. He was convicted in 1992 and sentenced to life imprisonment without the possibility of parole. Thus ending the reign of the ‘Teflon Don’, and in effect the point of demarkation for the end of the old school mafia syndicate. Nevertheless, John Gotti was the most notable gangster of the 20th century.


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