George 'Bugs' Moran.
 Bugs Moran (center)
Bugs Moran was born to Irish and Polish immigrant parents in 1893 and grew up in the north side of Chicago. He grew up streetwise and ran with numerous gangs committing more than 20 known burglaries and being imprisoned three times before he was 21 years old. He was soon an important member of Dion O'Banion's North Siders gang. The pair got on well together, both sharing the same sense of sick humor. In fact, Moran's sense of humor made him a celebrity with the newspapers setting him up to be a jolly murderer, always with a joke and a skip in his step. This good press probably put more of the public on the side of the O'Banion gang than their bitter rivals in the 1920's, the Capone Gang.
Bugs eventually became the leader of the North Siders after the demise of O'Banion and then Hymie Weiss, who both fell to Capone hit men, stepping up to the top spot after his predecessor Schemer Drucci was shot by police in 1927. With Bugs Moran leading the gang, Capone realized that the war with the North Siders would continue and more than likely become more bloody - such was Moran's way. It was hard to find a Mob shoot out in the 1920's in which Moran was not a leading player. Moran was the gun man who tried to finish off John Torrio after an ambush where Torrio was hit four times but, fortunately for Johnny, Moran's gun misfired. Moran was also in the lead car in the famous car cavalcade that drove past Al Capone's Cicero headquarters, The Hawthorn Inn, firing over 1000 shots into the building.
Moran had a pathological hatred for Capone, often referring to him as 'The Beast'. To annoy Capone more, Moran would frequently make truces with the Capone Mob only to break the peace within hours of coming to an agreement. To Moran, Capone was a low life especially since the Capone gang dealt in prostitution. A racket that the North Siders, being good wholesome Catholic church go-ers, refused to sanction.
The war between the gangs ended in a draw. Capone came closest to Moran in the Saint Valentines Day Massacre caper but Moran was late arriving that day and lucked out. Through the 1930's, Moran's power began to wane even though his nemesis, Capone, was now in jail. There may have been one high point in his life in 1936 when 'Machine Gun' Jack McGurn, the brains behind the St. Valentines Day Massacre, was shot dead. The press speculation was that Moran had a hand in the killing but McGurn probably fell foul of his own gang since his popularity by that time was at an all time low.
Moran's exploits thereafter never amounted to much. His crimes turned petty compared to what they had been in the 20's. He eventually moved to Ohio where he was arrested in July, 1946, for robbing a bank messenger of a paltry $10,000,  an amount that would have been loose change for him in his prohibition days. He was convicted and sentenced to ten years. After his release, he was again arrested for an earlier bank raid and sent down for another ten stretch at Leavenworth where he eventually died of cancer in 1957. George 'Bugs' Moran was given a paupers burial in a wooden casket in a potters field just outside the prison.