Al Capone: Chicago's Most Infamous Mob Boss

In June of 1930, Wilson got approval from the eccentric publisher of the Chicago Tribune to question one of his reporters. Jake Lingle was a friend of Al Capone's who flaunted the relationship.  Bergreen believed that Lingle wanted more than the profitable connection he had to the mob.  "His influence made him feel invulnerable when in fact his position was extremely vulnerable.  Acting as a double agent or even a triple agent was too thrilling to resist.  Not satisfied with playing this extremely tricky role, he agreed to inform on Capone for the federal government." 

Lingle's appointment was June 10, but he got a bullet in the back of his skull the day before. 

The uproar was deafening.  Capone rode it all out at his home in Miami Beach.  When asked about Lingle, Capone said, "newspapers and newspapermen should be busy suppressing rackets and not supporting them.  It does not become me of all persons to say that, but I believe it."

Meanwhile, Irey's Mike "De Angelo" checked himself into the Lexington Hotel, dressed himself in flashy expensive clothing and hung around the hotel bar, quietly reading the newspapers.  Eventually the Capone soldiers struck up a conversation with him and started to ask him questions about his background.

"We want the McCoy about you," one of the gangsters told him.  "You look like maybe you're on the lam and might be open to a proposition --and how do you know, we might have something for you."

De Angelo played along: "matter of fact, I am open for something, but it's got to be good.  If you want it straight, why I come out here in the first place is I didn't know but what maybe I could tie in with the Big Boy."

The gangster told him they had to do some checking first, but to hang around for a few days and they'd give him an answer.  De Angelo hoped he hadn't screwed up any of his fabricated identity or he would be a dead man.  A few days later, he was invited to meet with the mob and Capone himself at a big party.  Fully aware that Capone would wine and dine a traitor and beat him to death with a baseball bat,  De Angelo went to the party with trepidation.  Fortunately, Irey's thoroughness in crafting his agent's background paid off handsomely.  De Angelo was made a croupier in one of Capone's Cicero gambling joints.

Just before Ralph Capone's trial, De Angelo found out that the mob was going to focus on the government's witnesses.  It was good intelligence because Irey arranged for extra protection of the government witnesses.  The result was a guilty verdict for Ralph and no damage to government witnesses.

A few months later, De Angelo was joined by Graziano, who got a job checking on Capone's beer deliveries.  Just before Christmas, they uncovered a plot on Wilson's life and caught it just in time.  Now that the Capone organization knew about Wilson, Irey wanted to reassign him, but Wilson wouldn't have it.  This attempt on his life made him all the more determined to get Capone.