Al Capone: Chicago's Most Infamous Mob Boss

After the conference, Capone went to a movie in Philadelphia.  When the movie was over, two detectives were waiting for him.  In less than 24 hours Capone was arrested and imprisoned for carrying a concealed weapon.

Taking off his 11 1/2 carat diamond pinkie ring, Capone gave it to his lawyer to pass on to Ralph and was packed off first to the Holmesburg County Jail and finally to the Eastern Penitentiary where he stayed until March 16, 1930.  He left the running of the business to his brother Ralph, Jack Guzik and Frank Nitti "The Enforcer."

Another setback to Capone came when Ralph was indicted on tax evasion charges in October of that year.  Wanting to send a message to other gangsters, federal agents led Ralph away from a boxing match in handcuffs.  Persistent civil servant Elmer Irey had been investigating Ralph for years.  Ralph was nowhere near as smart as his brother Al when it came to hiding his wealth and financial transactions.  He was sloppy, greedy and dumb -- a natural target for an ambitious Treasury agent named Eliot Ness, who wiretapped his phones, and Nels Tessem, a highly-talented IRS agent, who scrutinized every financial transaction that Ralph made.   Nitti and Guzik also had their days in tax court as a result of this determined and exhaustive investigation.

With Al in jail and Ralph, Guzik and Nitti running the business, Ness was given the mission of collecting enough evidence of Capone's bootlegging to convince a grand jury that Capone was violating Prohibition laws as well as evading income tax.   Ness had his men tap Ralph's phones continuously.  With the intelligence Ness gathered, he was able to ram the front door of Capone's South Wabash brewery with a truck outfitted with a snowplow on the front.  Emboldened by this frontier lawman approach, Ness and his "Untouchables" continued to wiretap and shut down Capone breweries.

In mid-March of 1930, Capone was released from jail, a few months early because of good behavior. A week later, Frank J. Loesch, the head of the Chicago Crime Commission, put together a Public Enemies list which was headed by Alphonse Capone, Ralph Capone, Frank Rio, Jack McGurn, and Jack Guzick, all Capone colleagues.  The list was publicized in the newspapers and quickly adapted by J. Edgar Hoover as the FBI's list of the "Most Wanted" criminals.  So now, Al Capone, who wanted so much to legitimize himself as a contributing member of the community was Public Enemy Number One. He was enraged, humiliated and thoroughly insulted.

In that same month, Elmer Irey went to Chicago to meet with the agent-in-charge Arthur P. Madden to map out their battle strategy.  It became clear to both of them that they needed an insider in the Capone organization if they were going to be successful in the short-term.  Before he went back to Washington, Irey spent two days hanging around the lobby of the Lexington Hotel, posing as a salesman.  Once he developed a feel for the kinds of thugs that lived there, he came up with a brilliant idea: he would find two undercover agents who could, posing as gangsters, infiltrate the Capone organization.

"The obvious choice was Michael J. Malone....He was a good actor, with an ability to blend into any background.  He had nerves of steel and a sharp intelligence.   His dark, almost Mediterranean looks and his ability to speak Italian made him an ideal candidate for infiltration into the Italian-dominated Capone empire" (Ludwig, Smyth).  Another undercover agent was selected to be his partner in this venture.

Malone would take the name De Angelo and the other agent Graziano.  Major efforts were made to create false identities for the two men as small-time Brooklyn racketeers.   They knew that every single detail of the forged identities would be scrutinized and that their lives depended upon how well they studied for their parts.

Neither Graziano nor De Angelo could ever be seen or heard talking to Irey or Madden, so an intermediary had to be found.  The third agent in this venture was Frank J. Wilson, a 43-year-old star in the agency.  Wilson would not only be the contact man for Graziano and De Angelo, he was to coordinate intelligence and evidence and perform some of the investigations himself.