"October 29th, 1930" Tommy, Paulie, and Sam are doing their regular collection rounds.

"September 3rd, 1932" It's 1932 and the Lost Heaven Grand Prix is around the corner. Paulie, Sam, Don Salieri, and other fellow race fans put their money on Mikey Dunne, a local racing driver. However, Don Salieri told Tommy that a European racer is entering the race and putting Mikey at a disadvantage, as well as people's bets at risk. In order to give Mikey a fighting chance, Don Salieri figured that Tommy should boost the European's car, bring it to one of his mechanics to be tinkered, and return the car. "November 12th, 1932" One night, when Salieri's Bar is about to close, Luigi asked Tommy to take his daughter home in order to keep her safe from men who tried to make an advance on her.

"November 13th, 1932" Don Salieri is not pleased to know that a group of punks have been harassing Sarah, and so he asks Tommy to teach them a lesson.

"November 20th, 1932" Following the previous event, it was revealed that one of the hoodlums who Paulie capped was Billy Ghillotti, son of the city councilor. It was also revealed that the other person survived the ordeal, putting the family at risk.

"February 2nd, 1933" The year is 1933. During these days, Frank had to deal with day-to-day orders for the family, and this time, he wanted Tommy to help Sam and Paulie secure a shipment of booze from Canada.

"April 3rd, 1933" About two months after the botched booze deal, Tommy meets Don Salieri at the park, where Don Salieri reveals that the family has a mole.

"August 31st, 1933" While being driven by Carlo, Don Salieri told Tommy about a prosecutor who's on Morello's payroll and wiling to drop details about Salieri family's involvement in Billy Ghillotti's death. The Don instructed Tommy to meet Salvatore, a safecracking expert, and get rid of the incriminating evidence. "September 22nd, 1933" While supervising an activity at the warehouse, Paulie told Don Salieri and the crew about a whiskey distiller named Gates, whose father owns a distillery in Kentucky and exclusively supplies Kentucky whiskey to Morello family. Paulie, knowing that Gates is bringing a shipment that night with his whole crew on board, figured that staging a heist may result in a good deal. Tommy, thinking that the Canadian needs to be replaced after the botched deal, agrees to meet Gates at the parking lot downtown.

"May 1st, 1935" Tommy took Don Salieri to his favorite restaurant, as Carlo called in sick. "May 2nd, 1935" In order to scare Morello's affiliates and give the Salieri family an advantage in the war against the Morello family, Tommy is sent to liquidate Roberto Ghillotti, who's celebrating his birthday by throwing a shindig on a steamboat.

"May 13th, 1935" The Salieri family is now looking to waste Morello family's underboss Sergio Morello, a feat that's easier said than done due to Sergio's apparent luck. Tommy is sent to do the job after Vincenzo and Sam failed to do so.

"May 20th, 1935" Sergio's death is followed by a series of gang wars, which led to Don Morello's first public appearance after went into hiding for some time. One day, he's hosting a charity gala, an opportunity that's used by the Salieri family to rub him out.

"July 15th, 1938" The year is 1938. Election day is coming, and Don Salieri puts a special concern on Mr. Turnbull, one of the governor candidates, for his promise to eradicate organised crime, threatening Salieri's family. Knowing that Mr. Turnbull is a hypocrite due to him having an affinity towards prostitutes, Don Salieri wants to rub him out during one of his campaign rally. "September 30th, 1938" A shipment of imported cigars belonging to the Don had been impounded, and Tommy, Paulie, and Sam are sent to reclaim them from the Federal Customs Impound. In response to Tommy, who thinks that the job appears to be small time, Don Salieri added that the cigar shipment was just a front for smuggled diamonds that even the Feds haven't discovered. Along the way, Paulie discusses his ideas for robbing the Grand Imperial Bank.

"November 3rd, 1938" Following the cigar heist, Paulie persuaded Tommy to do a score in the Grand Imperial Bank, which Tommy agreed after Paulie ensured that the score will be enough for them to retire from criminal life, something that had taken its toll on Paulie and Tommy.

After the bank job, Tommy returned home to a suspicious Sarah, who thinks that Tommy's hiding something from her. Tommy decided to pay Paulie a visit at his apartment to decide what to do with the score; however, Tommy was distraught after he found Paulie dead. Shortly after, he received a phone call from Sam, who told Tommy that Don Salieri discovered the score. Tommy decided to meet Sam at the art gallery.