Al Capone: Chicago's Most Infamous Mob Boss

Back in Chicago at the beginning of 1926, Capone was in excellent spirits.  Not only had he made his mark in New York, but his whiskey deal would change the face of interstate transportation.  Young men with a thirst for adventure and the need for money made a good living working as one of Capone's truckers.

In the spring of 1926, Capone's run of good luck hit a snag.  On April 27, Billy McSwiggin, the young "hanging prosecutor" who had tried to pin the 1924 death of   Joe Howard on Capone,  met with an accident.  He left the home of his father, a veteran Chicago police detective, and went with "Red" Duffy to play cards at one of Capone's gambling joints.  A bootlegger named Jim Doherty picked them up in his car.

Doherty's car broke down and they hitched a ride with bootlegger "Klondike" O'Donnell, a bitter enemy of Capone.  The four Irish lads went on a drinking binge in Cicero with O'Donnell and his brother Myles and ended up at a bar close to the Hawthorne Inn where Capone was having dinner.  O'Donnell's cruising around in Cicero was a territorial insult.

Capone and his henchmen, not realizing that McSwiggin was in the bar with Myles O'Donnell, waited outside in a convoy of cars until the drunken men staggered out.   Then out came the machine guns and McSwiggin and Doherty were dead.

Capone was blamed.  Despite the blot on McSwiggin's integrity for keeping company with bootleggers, sympathy was with the dead young prosecutor.  There was a big outcry against gangster violence and public sentiment went against Capone.

While everyone in Chicago just knew that Al Capone was responsible, there was not a shred of proof and the failure of this high-profile investigation to return an indictment was an embarrassment to local officials.  Police took out their frustrations on Capone's whorehouses and speakeasies which endured a series of raids and fires.