Successfully complete Story mode to keep your previous amount of money and your Blacklist entries. Successfully complete Story mode and defeat Chester to have him as an ally. Successfully complete Story mode with all five characters to unlock the "Movie Viewer" option. Successfully complete Story mode with one of the following ranks to unlock the indicated bonus(es) when a new game is started:

Czar: Charisma Pheromone. Governor: Fatima as an ally, Charisma Pheromone.
Ruler: Eugene and Fatima as allies, Charisma Pheromone. Investor: Turkey. Super-Rich: Quincy as ally, Turkey. Ultra-Rich: Tracy and Quincy as allies and Turkey. Samurai: Bulletproof vest. Beast: Ignacy as ally, bulletproof vest. Tyrant: Gregorio and Ignacy as allies, bulletproof vest. Good Citizen: The Hole sells weapons and items. Boss: Melvin as ally and The Hole sells weapons and items. Don: Wallace and Melvin as allies and The Hole sells weapons and items.
Godfather: Zanetti, Wallace, Melvin as allies, and The Hole sells weapons and items.