The mob then turns its attention to Morello's brother Sergio, but a car-bomb attempt ends with Sergio's mistress dead instead of him. A second attempt on Sergio's life is botched by a jammed gun, and a third ends with Salieri's hired hitmen turned to paste on a railroad track. After witnessing all three failures, Tommy takes it upon himself to chase Sergio down, ultimately killing the lucky bastard in a dramatic waterfront shootout.
Finally, it's time to cap Morello himself. Tommy, Paulie and Sam are sent to assassinate him while he takes in a show at the theater, but by the time the three arrive, Morello's already leaving. This is one of the few points in the game where things can develop differently, and the encounter either ends with Morello boarding a plane (which is then shot down by Tommy) or driving his car off a cliff, at which point it explodes. Either way, the man is doomed to a fiery death.
Following Morello's death, the action cuts back to the continuing chat between Tommy and Norman. As the two talk, Tommy reveals something interesting: in 1920, Salieri and Morello were be friends, working together as captains for a crime boss named Peppone. Ambition got the better of them, though, and their actions got the old man killed., After that, it didn't take too long for Morello and Salieri to eventually turn on one another. When he learned this, Tommy says, he realized that that would be his likely fate as well: killed by his friends because someone got too greedy.
With Lost Heaven's criminal operations under his near-complete control, Salieri hasn't become any less ambitious. A "tough-on-crime" politician who's secretly running brothels (without kicking up anything to the Salieris) has begun to irritate him, and so he orders Tommy to take care of the problem. Tommy's equipped with a scoped Mosin Nagant rifle for the job, and - after climbing to the top of a tower in an abandoned prison - Tommy draws a bead on the politician during a speech and dramatically murders him in front of a gathered crowd.
Strangely, it's not the assassination, but an insignificant-seeming hijack job that turns Tommy's world on its ear. Salieri learns about a shipping manifest from a local importer, and suddenly develops a craving for some expensive cigars that are being shipped in. Ignoring their protestations that it's a small-potatoes heist, Salieri orders Tommy, Sam and Paulie to steal a truckload of the things.
While the three drive to the shipping yards to steal the truck, Paulie floats the idea of knocking over a medium-sized, poorly guarded bank he knows about - but because an independent robbery is something the Don would likely kill them for, Sam and Tommy immediately refuse. But after the surprisingly dangerous caper nearly gets them killed, Paulie and Tommy investigate a smashed crate and find out that the "cigars" are actually smuggled diamonds. After Salieri fails to tell them about the real nature of the haul - or about the money he's going to get from selling them - Tommy decides to help Paulie out with the robbery.
The way Paulie lays it out, the robbery's going to be one last, big score that will enables Paulie and Tommy to take it easy. Paulie turns out to be exactly right, for once; the daring robbery goes off without a hitch, and the two make off with a huge fortune, stashing the money at Paulie's apartment and agreeing not to spend any of it for the time being, so as to keep anyone else from finding out.
The next day, Tommy stops by Paulie's apartment and finds the door unlocked. Stepping inside, Tommy finds Paulie lying dead on the floor, his back riddled with gunshot wounds. The money's gone, and just then the phone rings. It's Sam, and he sounds scared. He was hoping to warn Paulie, he says, but it looks like he called too late; Salieri's found out about the robbery, and has marked both Paulie and Tommy for death.