Thomas Bronk
Young Al Capone catches the eye of Johnny Torrio, a criminal visiting New York from Chicago. Torrio invites Capone to move to Illinois to help run his Prohibition-era alcohol sales operation. Capone rises through the ranks of Torrio's gang and eventually takes over. On top, he works to consolidate his power by eliminating his enemies, fixing elections to his advantage and getting rich. In his spare time, Capone courts the principled Iris Crawford.
Frankie Piano
After runaway Ben Young is robbed and left on his own, he is taken in by Lil, the head of a Chicago brothel. Acting as a surrogate mother for Ben, who thinks she runs a boardinghouse, Lil gets him a job with Francis Sullivan at the local newspaper. As Ben is exposed to the workings of the big city, he realizes the extent of government corruption and sets out on the daunting task of reforming Chicago politics, finding several allies along the way.
Sammy
A sleazy but ingenious criminal masterminds a heist at a sold-out sports arena. He hires a motley crew of henchmen, seduces the middle-aged head cashier, and plans some brutal ruses to elude the law. But he's his own worst enemy.
Rick is pledging a snooty fraternity at college. He feels out of place because he's a poor kid from the wrong side of town and picks up extra money by fighting in the ring. He doesn't want his potential fraternity brothers to find out about his background or how he makes his money. Trouble arises when the rich, spoiled girlfriend of one of his fraternity "bros" comes on to him.