Al Capone is the first name that comes to mind when someone thinks of the Prohibition era or gangsters.  Alphonse Capone was raised as a good boy by his Italian family.  He started out working for a munitions factory and then as a paper cutter.  After this, he was hired as a bartender at Frankie Uale’s new nightclub, the Harvard Inn. 

Capone became very popular with the customers and with his new boss, but then his luck turned when he waited on a young couple.  The girl was young and pretty and Capone was spellbound.  The first words out of his mouth were, “Honey, you have a nice a** and I mean that as a compliment.”  The boyfriend then proceeded to punch Capone and soon a fight erupted.  During this fight, Capone was slashed with a knife across the face.  This is where he earned the name Scarface. 

At the age of 22, Capone moved to Chicago with Johnny Torrio and took over a nightclub, gambling den, and brothel called the Four Deuces.  He soon moved up the underworld ladder and became a major player in the speakeasy business, owning almost half of Chicago's speakeasies.

Luck was with him, until the attempted assassination of another powerful crime figure, Bugs Moran.  This event is more commonly known as the St. Valentine’s Day Massacre, where 4 bootleggers were caught and killed by Capone’s fake policemen.  Unfortunately, Moran was not among those bootleggers.  No one was ever brought to justice for these crimes. 

Capone was eventually arrested and convicted of income tax evasion.  He was sentenced to 11 years in prison, $50,000 in fines and another $30,000 in court fees.  He died at the age of 48, just after being released from Alcatraz early on good behavior.