Edward J. O'Hare - Chicago

Chicago

Divorced from his wife Selma in 1927, O'Hare moved to Chicago. Selma stayed in St. Louis with her two daughters Patricia and Marilyn, while Butch went to the U. S. Naval Academy.

In Chicago, O'Hare met Al Capone, the man who ran Chicago during Prohibition. When Charles Lindbergh performed his famous transatlantic flight in 1927, Capone was among the first to push forward and shake his hand upon his arrival in Chicago. Capone's gang was the dominant gang in the city. An entrepreneur new in town, as E.J. was, had to choose a gang, just as today he would have to choose a business insurer. E.J. later fell in love with secretary Ursula Sue Granata, the sister of a State Representative with ties to the Mob. The engagement went on for seven years because, as Catholics, O'Hare's divorce from his wife Selma made it impossible for the couple to have a church wedding. However, O'Hare was hopeful that a request for a dispensation from the Vatican would come through by 1940.

O'Hare and Capone began collaborating in business and in law. O'Hare made a second fortune through his ties to Capone. In 1930, E.J. asked John Rogers, a reporter for the St. Louis Post-Dispatch, to arrange a meeting with the Internal Revenue Service (IRS). John Rogers organized a meeting with IRS agent Frank J. Wilson. After lunch, E.J. agreed to turn over key financial records of Capone's. The IRS's overall goal was to wreck Capone financially by destroying his bootlegging business. Agent Frank J. Wilson's job was to convict Al Capone of tax evasion.

E.J. O'Hare played a key role in Capone's prosecution for tax evasion. Frank J. Wilson, then government investigator of the Internal Revenue Service (and later Chief of the U.S. Secret Service between 1937 and 1946) revealed in the 26 April 1947 issue of Collier's magazine how Capone was convicted: "On the inside of the gang I had one of the best undercover men I have ever known: Eddie O'Hare." By 1930, E.J. O'Hare was working undercover for the Internal Revenue Service of the Treasury Department. It is believed O'Hare directed investigator Wilson to the Capone bookkeeper who became a key witness at the 1931 trial, and he also helped break the code with which Capone's bookkeepers kept ledgers at various gambling houses throughout the 1920s. During the Capone trial, O'Hare tipped the government that Capone had fixed the original jury that was to hear the case in the court of Judge James Wilkerson. Thus alerted, Judge Wilkerson switched juries with another federal judge just as the Capone tax trial was set to begin (depicted in the 1987 film "The Untouchables").

Al Capone was found guilty on five of twenty-two counts and sentenced to eleven years in a federal prison. Al Capone arrived at Alcatraz in August 1933.