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Josh, on his way to tell Capone that Moran has murdered Jake, recalls his last day as an errand boy for Capone three years ago. Josh earns another chance at shooting Moran, misses again, and Moran blows up Mason's still. Two plus years later, the epilogue.

McGurn, sympathetic to Josh's dilemma, or maybe not, puts Josh and Jake up to ambushing Moran. Now Josh has to plan a funeral. On his way to update Capone, Josh recalls his first job with Big Al.

Josh recalls fishing on Spider Lake in Mercer and lives to tell about it but remembers why he needs to shoot the lawyer who bails him out of jail.

Ruth is upset to hear from her boss, Mr. Olson, that Josh had come by to bribe him on Capone's orders. She starts rethinking her job at the bakery. In the meantime, Josh sits in jail remembering that the lawyer coming to bail him out is the same guy trying to kill his father.

Capone sends Josh out to bribe his upcoming jury. First juror, Mr. Olson, his former boss, brings back memories of his accident. Josh, trying to do right, is thrown in jail for jury tampering.

Bo, out of other ideas and money, agrees to sell his whiskey to McGurn to rescue Josh from the mob. This leads to a golf game with Al Capone, the decision maker, and that leads to a request for a secured loan from a lady in Lake Forest.

Ruth tries to make dinner for the Masons but a remark by Bo brings her back to her eighteen months in the insane asylum following the loss of her baby and the suicide deaths of her parents.

Josh and Ruth relive memories from two years ago. Bo goes down to his bank to withdraw their life savings so the four of them can make a run for it-away from the mob, away from Chicago.

Bo Mason turns down Josh's request for help in getting out of the mob. Chauffeuring McGurn about town on his whiskey route, a comic standoff in a local dive ends in gunfire.

We meet Bo Mason, neighborhood bootlegger, whose only customer suspects him of disloyalty and orders a stakeout preparatory to killing him. We meet Josh's Dad, an alcoholic, in a scene re-motivating Josh to quit the mob or die trying. The Moran gang bungles a stakeout.

Josh is sent to guard the cleaners and becomes involved with a murder. Ruth remembers more than she wants to about Dion, her English teacher.

Josh Andrews, minor Chicago Prohibition hoodlum, discovers he has bitten off more than he can chew when he takes Ruth, a former classmate, to dinner, as a prelude to sex. Smitten again, he agrees to quit the mob so he can date Ruth. That doesn't work either.