The prohibition era gangsters of the 1920s are some of the most famous (or infamous) of all time, perhaps due to a combination of their unthinkable killings and crime, and the romanticization within popular culture. Killers, thieves, bootleggers, smugglers; we take a look at Chicago’s top 5 most notorious mobsters and the illicit behaviour they were best known for.
Alphonse “Al” Capone
Al Capone, unquestionably America’s best known gangster —also known as “Scarface”— became a symbol of the collapse of law and order in America during the 1920s and 30s. Capone was known for being very smart but also extremely brutal and quickly worked his way up through the ranks to become the leader of one of Chicago’s biggest criminal gangs. He was involved in illegal gambling, bootlegging and prostitution, and battled the North Side gang for control of the underground. As well as causing a huge amount of pain and death, he opened up soup kitchens and strutted around town in custom suits, cigar in mouth and sipping Templeton Rye. Over the years he was arrested multiple times and was eventually sent to jail in 1931 for tax evasion where he served eight years. He was released on parole and suffering from Syphillis related ailments, he spent the rest of his life at his estate in Florida and died of heart failure in 1947 at the age of 48. Every mobster cliche today is in some way a result of Al Capone and the icon that he became.
Dean O’Banion —“Deanie” or “Dion”— was an Irish-American mobster and became the main bootlegging rival of mobsters Capone and Torrio. Following brief encounters in jail in 1909 for safecracking and assault, he rose to become one of the first to recognize the potential of bootlegging and in 1921 he bought a flower shop which served as a legitimate front for his criminal wrongdoings.
To avoid bloody battles, O’Banion wanted peace with his rivals so he formed a deal with the South Side and other Chicago bootleggers to work out a system of territoires. After three years he became dissatisfied with the agreement and was shot dead by gunmen of rival mobsters, the Genna brothers whilst working in his flower shop. O’Banion’s death sparked the great gang war of the 1920s where the North and South sides fought for five years, culminating in the brutal killing of seven North side gang members in the St. Valentine’s Day Massacre, 1929.
In the early 20s, John Dillinger was sent to jail for robbing a grocery store but escaped to resume his criminal career, forming one of the most coordinated and destructive gangs who went on to rob eleven banks, leaving fifteen people dead and another seventeen injured. He was briefly captured again for the murder of a policeman but whilst awaiting trial he managed to slip free, this time undergoing surgery to alter his appearance and avoid redetection. He became one of the most infamous gangsters and bank robbers; authorities branded him as America’s “Public Enemy No .1.” Dillinger’s life came to an end when a lady friend revealed their whereabouts and he was fatally shot by FBI agents outside a movie theatre. The next day, 15,000 people lined up to catch a glimpse of his bullet-riddled body when it was put on display at the county morgue.
George “Bugs” Moran
Childhood friend and later right hand man of Dean O’Banion, George “Bugs” Moran subsequently became leader of the North side gang, rivaling Al Capone’s South side in bloody warfare. Moran was presumably the target of the St. Valentine’s Day Massacre in 1929 but narrowly avoided being killed by Capone’s gang as he ran away from the scene. Several other members of his gang were slaughtered in a garage. After this, he took several trips to prison for petty crimes including mail fraud and robbery but was eventually sentenced to ten years for bank fraud; it was during this time that he died of lung cancer.
Lester Joseph “Baby Face” Nelson
Born Lester Gillis, this notorious gangster was called “George” by his family, “Baby Face” by members of his first gang and used the surname “Nelson” as an alibi. He stood at only 5ft4 but preferred to be called “Big George”. Dabbling in car theft and petty shoplifting as a teen, he later moved on to ruthless armed robberies and deadly gunfights.
After associate John Dillinger died, Nelson was listed as the new “Public Enemy No .1.” He was involved in multiple murders across many small towns and cities, of which his victims included three FBI agents. In 1934, at age 25 he was gunned down in a shootout with federal agents and died in a Wilmette safehouse.