Plot
Big Louis Costillo (Harry J. Vejar), the leading crime boss of the South Side, is killed, apparently by Tony Camonte (Paul Muni) acting on the orders of Johnny Lovo (Osgood Perkins). Lovo then takes control of the South Side with Tony as his key lieutenant, selling large amounts of illegal beer to speakeasies and muscling in on bars run by rival outfits. However, Lovo repeatedly warns Tony not to mess with the Irish gangs led by O'Hara who run the North Side. Tony soon begins to ignore these orders, shooting up bars belonging to O'Hara, and attracting the attention of the police and rival gangsters. Lovo begins to realize that Tony is out of control and has ambitions to take his position. Meanwhile, Tony pursues Lovo's girlfriend Poppy (Karen Morley) with increasing confidence. At first, she is dismissive of him, but pays him more attention as his reputation rises.
Tony eventually decides to declare war and take over the North Side, and sends one of his best men and close friend, the coin flipping Guino Rinaldo (George Raft) to kill O'Hara in a florist's shop that he uses as his base. This brings heavy retaliation from the North Side gangs now led by Gaffney (Boris Karloff) and armed with Tommy guns, a weapon that instantly captures Tony's dark imagination. Tony leads his own forces to virtually destroy the North Side gangs and take over their market, using tactics such as those used on the Valentines Day Massacre. This proves too much for Lovo, whose organization has been effectively hijacked by his ambitious deputy, and he arranges for Tony to be assassinated while driving in his car. Tony manages to escape this attack, and he and Rinaldo kill Lovo in revenge, leaving Tony as the undisputed boss of the city.
Tony's actions have provoked a public outcry and the forces of the law are slowly closing in. Tony's problems increase when his sister Cesca (Ann Dvorak), whom he is overprotective of, secretly marries his friend Guino. After discovering the two of them together, Tony kills his friend leaving his sister distraught. This provides the police the opportunity they'd been waiting for and they move to arrest Tony for Guino's murder. Tony holes up in his house and prepares to shoot it out. His sister comes, planning to kill him, but ends up helping him to fight the police. When she is killed by a stray bullet, Tony's confidence collapses. As the apartment fills with tear gas, he leaves down the stairs and is confronted by the police. Tony pleads in cowardly fashion for his life then seems to make a break for it, but is mowed down by police fire - apparently suicide by cop.
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