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A teenager in Prohibition Chicago, haunted by disasters, breaks all his childhood vows of clean living and becomes a minor hoodlum. When he tries to recapture his dreams with a feisty former classmate, she says first quit the mob. He discovers that one doesn't just quit the mob and live to tell about it; he must find another way out.
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A fortunate son and failed lawyer turned failed banker turned struggling stockbroker inexplicably marries well, crosses paths with Al Capone and determines, as his crowning achievement, to reform Capone and introduce him into polite society, of which he is its most marginal member. This mission, which Capone endorses while systematically murdering his competitors, and then his allies, poses one question. Is Capone ready for reform?
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Blackie Lolordo gets his 15 minutes of fame. Elliot gets invited to the banquet.
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Elliot thinks he's doing Capone a favor. Scalise and Anselmi decide it's time to repent.
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Dion plants some evil seeds. Moran plots revenge; Capone plans a harvest.
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Bo Mason plays a reluctant role in St. Valentine's Day, Feb. 14, 1929. Dion switches sides, meets the Moran gang, where he can cause more trouble.
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Jack McGurn organizes a reply to the Northsiders. Dion's French Lick connection is discovered.
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The Cosgroves Christmas in Chicago. Patsy Lolordo is sent a message.
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Dion helps out Capone and concludes his French Lick chapter, he thinks. The French Lick parents, Blanche and Reuben Cosgrove, become grieving grandparents.
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Capone shows his management style, Guinta tries to blow up Mason's still.
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Elliot tries to repay a favor, the Lolordos are promoted above their level of competence? We meet Bo Mason and Hoptoad Guinta, bootleggers, and mortal enemies.
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Elliot wins and loses at the races, Capone does Elliot a favor.
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Elliot's wife, Bunny, does not endorse his new buddy; the Lolordo's send Tony Lombardo a message.
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Dion, trying to make a buck, just misses getting killed; Elliot does Capone a favor.
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We find Dion on Chicago's west side, causing more trouble. We're introduced to Patsy and Blackie Lolordo, wannabe bootleggers scheming to get a pay raise out of Capone, and Elliot Fulton, a stockbroker from Lake Forest, who rubs Capone's gang the wrong way.
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We're introduced to Joe Dion, who comes to French Lick, excites women, causes trouble, tries to direct play but flees for Chicago just in front of the posse. Capone sends a message to Frankie Yale, one of his whiskey suppliers.
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Hymie Weiss, leader of Chicago's Northside gang during the Prohibition, refuses an offer from Al Capone.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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