Prologue
The year is 1938, in the city of Lost Heaven, Illinois. Detective John Norman steps off the train and walks into a dingy restaurant, where someone important is waiting for him. Norman is a seasoned detective who gained his experience working in Empire Bay. The other man is Thomas Angelo, Tommy to most everyone he knows, born to a poor family on the island of Sicily in 1900. He is a former mobster of the Salieri crime family, and he has contacted Detective Norman about a proposition.
Norman joins Tommy at a table and the two men get acquainted. Norman has been appointed to investigate the death of Don Marcu Morello, who headed the Morello crime family. However, in the three years since his death, the killer has not been found, no new leads have turned up and the case has been left unsolved. Tommy is seeking protection for his wife and daughter following his criminal activities, and he has some information which could solve the Morello case and leave some enduring implications to come.
Norman quickly figures out that Tommy is only asking for his help because he is on the run from the family he once served. Somehow or other, Tommy has earned the ire of someone vindictive and powerful, who will not stop chasing him until he is eliminated. He is exhausted, flat broke, and constantly on alert. Both he and Norman understand that he is faced with two stark options; either walk out of the restaurant and risk being found by his pursuer, or stick around and relate his experiences so that he may see his daughter reach adulthood.
With no other choice, Tommy Angelo begins his story. It all started when he was a taxi driver in 1930...
1930 — Wrong Place at the Wrong Time
The date is 20 September 1930, and it is nighttime in Lost Heaven. Tommy is tending to his taxicab when he hears a car crash nearby. Upon investigating, he finds a man with a gun calling to another, who notes the nearby taxi. The one with the gun points it at Tommy and hops into the backseat while the other jumps in the passenger seat and forces Tommy to drive. The taxicab is soon followed by armed men gunning for Tommy's new passengers, Paulie Lombardo and Sam Trapani. Tommy's driving soon makes quick work of their pursuers, particularly when Tommy accelerates the taxi and vaults over the West Harbor Bridge as it raises.
Once the gunmen are off their backs, Tommy drives Paulie and Sam to a place called Salieri's Bar in Little Italy. Paulie insists Tommy wait outside after dropping them off in order to receive a reward for his services tonight. Sam walks out of the bar soon after, almost looking like he's preparing to shoot Tommy where he sits as he prepares to drive off. To Tommy's surprise, however, Sam actually pulls out an envelope full of cash. The gangster explains that he and Paulie's boss, Don Salieri, is appreciative of Tommy's efforts, and thus has given him this money to fix his taxi (with the understanding that Tommy mustn't breathe one syllable of what happened to anyone). His parting words are an offer of anything, including work if Tommy is so inclined.
The money in the envelope is more than enough to fix the taxi, but Tommy decides attaining this level of money through the work Sam is in has a risk that far outweighs any reward. As such, he decides to forget what happened that night. For now, anyway...
The date is 23 September 1930, and today is yet another dreary day at work for Tommy Angelo. He drives his taxi around the city, taking passengers to their destinations as any cabbie would. His customers are mostly dismissive and ingratious and he earns a lowly pittance for his services. But at least he has a livelihood and an income, while so many others are left jobless and penniless in the throes of what will be called the Great Depression.
While taking a coffee break, Tommy is attacked by two men named Dino and Lou. Lou wrecks the taxicab with a baseball bat, while Dino drags him outside and beats him. Dino and Lou work for Don Morello, whose goons chased Paulie, Sam and Tommy three nights ago. They are none too pleased with Tommy's actions and are looking for some payback. As the goons discuss crippling the poor cabbie, Tommy shoves Dino into Lou and runs off through the nearby alleyway. Dino and Lou decide to run after him, and the chase is on.
Tommy runs through the alleys of Little Italy as fast as his legs can carry him, but Dino has brandished a pistol and is now shooting in his direction. Dodging bullets, cars and people alike, Tommy ends up back at Salieri's Bar, where Sam and Paulie escort him inside and confront the two rival gangsters. Dino tries to downplay their actions, but Sam makes it perfectly clear to the goons that hurting Tommy will not end well for them. Paulie brandishes his shotgun and threatens Dino and Lou to either leave empty-handed or face the consequences. The goons reluctantly slink off, while Sam and Paulie decide to take Tommy to meet the Don himself, Ennio Salieri.
Sam and Paulie lead Tommy into a meeting room in the back of Salieri's Bar, and soon the Don enters alongside his consigliere, Frank Colletti. After hearing Tommy's story, Salieri offers a loan to repair Tommy's taxicab, but Tommy politely refuses. Instead, he wants to get payback on the gangsters who wrecked his day; in amusement, the Don gives him such permission. Salieri assigns Tommy to wreck some cars belonging to Morello's gangsters in order to show that he is fiercely protective of working men in his territory. He assigns Paulie to ride with him and directs them to a parking lot by Morello's bar where the gangsters often park their cars.
Before leaving for the job, Paulie introduces Tommy to the other important people in their employ. The Salieri family's armourer Vincenzo "Vinny" Ricci gives them some baseball bats and fire bottles. Their mechanic Ralph provides them with a dinky old-fashioned car that Paulie continually complains about.
After a slow, gruelling journey, Tommy and Paulie park their car opposite Morello's place. Paulie teaches Tom how to move quietly and goes to distract the single guard, while Tommy sneaks around and takes care of him. Paulie and Tommy open the gates and get to work, smashing the cars with the baseball bats and burning them with the fire bottles. The explosions alert some of Morello's other goons, but Paulie and Tommy are able to dispatch them. They decide to further stick it to the Morello family by stealing Dino's car, losing the police officers that such a scrap tends to attract.
Salieri is suitably impressed with Tommy handling himself. For that matter, Tommy finds wrecking Morello's cars rather cathartic and is excited to earn more than a pittance in the mob. Salieri explains that loyalty and trust trump everything else in his family. He trusts Tommy to be capable and loyal, but if Salieri's trust is broken, he will not hesitate to bring retribution on the person who wronged him. After today, Tommy Angelo is formally invited into the family.
The date is 29 October 1930. Tommy has been working in the Salieri family for a few weeks now, mostly doing odd jobs. Today, he is assigned on a run with Sam and Paulie to collect from various businesses that pay the Salieri family for protection. Before they set out, Vinny teaches Tommy the basics of gunfighting, while Ralph teaches Tommy how to break into cars with a lockpick instead of just breaking the window.
The first collection of the day is from Al Bertorelli's bakery in Little Italy. While the visit is civil if rather tense, and Al is deep in debt, his payment is attained with no issues. The second collection is from a Chinese shopkeeper in Chinatown. Paulie goes into the shop alone, while Tommy and Sam wait in the car as violent noises can be heard from inside. Paulie returns with the payment, explaining that he was bashing the new owner's head against his shop counter to remind the Chinese gangs of their place in the hierarchy.
Things change for the worst when the gangsters reach their third collection, from Clark's Motel outside of town. While Tommy is waiting for Sam and Paulie, gunshots ring out in the motel. Paulie runs out with a small gunshot wound, and an armed man warns the mobster that the motel is now under the protection of Morello. Paulie tells Tommy that Sam is still inside the motel, and that Morello's thugs are working him over to get information out of him. With Paulie out of action, Tommy takes it upon himself to save him.
Tommy slips into the motel unseen and eventually gets into a gunfight with the Morello gangsters. Once they're dead, Tommy finds Sam in a decent-enough condition, but one of Morello's remaining goons flees the motel with the money that they were meant to collect. Tommy pursues him in a car and catches up to the gangster, eventually killing him and reclaiming the collection payment. While Tommy has now seen the darker side of life in the mob, the pull of what it can bring him is far too strong for him to leave now.
Norman takes a break in the story to talk of how Tommy seems to have gotten where he was in Salieri's mob on nothing but dumb luck, though Tommy sees it as having been fate. At that time, Salieri didn't have nearly the pull in the city that he has now, and life wasn't so glamorous for his mob. Don Salieri made money and had some low-level policemen in his pockets, but Don Morello made far more money and effectively had the whole city under his heels, be it through the right payoffs or the right threats. To emphasize this, Tommy tells a story about a boxer named Joey Crackers.
Crackers was stopped at a crosswalk one day, minding his own business, when another car rear-ended him. He cussed out the driver, only to realize with abject horror that the other driver was Morello himself. Joey desperately tried to walk back his words and placated the Don as best he could. However, Morello was in a furious mood and grabbed a tire iron out of his trunk. While Joey tried to say that the damage was only minor, Morello simply clobbered him to death with the tire iron as two beat cops nervously walked away.
Norman is incredulous and figures that the story as Tommy heard it has to be false. Joey Crackers was in Morello's employ and made the family good money by "losing" certain fights and letting them win the bets, so it would make no sense to throw away such an asset over nothing. Yet all the same, Morello still murdered Joey in broad daylight and left without so much as a ticket. While Tommy isn't entirely certain if there wasn't some other motive behind it, he agrees with Salieri's assessment of Morello not thinking clearly when he was angered.
When Tommy is asked if he ever had any run-ins with Morello's gangsters, he says that the first couple of years in the Salieri family were mostly uneventful, but there were a few times that were pretty fun.
1932 — Fateful Encounter
The date is 3 September 1932, and the Lost Heaven Grand Prix is scheduled for tomorrow. Salieri calls Tommy to the bar needing his help regarding Mikey Dunne, the Salieri family's favourite racer. Mikey is an experienced hotshot driver who is damn near invincible on the race track. Every time Salieri bets on Dunne's races, he makes his money back and more several times over. In that time, Mikey has established himself as a local superstar among the citizens of Lost Heaven.
As such, when Dunne is due to race in this year's exhibition, Salieri places his money down on him, as have several others in the family and their neighbours. However, there is a problem: Morello has arranged for German racer Martin Lichtenberg to compete in the race. He is an experienced hotshot driver just like Mikey, and his car makes Mikey's look like a wind-up toy. Injuring or otherwise harming Martin is not an option, as even if he could be found, his sudden disappearance would make the betters believe the race is rigged, and all bets would likely push.
Instead, Salieri orders Tommy to go to the racetrack and steal Lichtenberg's car with the help of a guard who is a friend of Ralph's. Then he must take the car to Lucas Bertone, a mechanic who sometimes offers his services to Don Salieri. Bertone will tinker with the motor to make it sputter, and Tommy must take the car back before the guard's shift is over.
Tommy makes it to the track at midnight and meets Ralph's contact Bobby. Bobby leads him to Lichtenberg's car, but he warns that the guard working the shift after him is rather disagreeable, so he has to be quick. Tommy hoofs it through the city streets and over the Giuliani Bridge to Bertone's garage. Upon arrival, Lucas works his magic on the motor and Tommy makes it back to the track just in time, in spite of Lucas' "tuning". It seems everything is set for Mikey and his win.
Race day begins on 4 September, and a sizeable crowd has turned up for the Grand Prix. Tommy, Paulie and Sam are shooting the breeze with about a half hour left before the race starts. Suddenly Frank approaches Tommy with a change of plans — Tommy will take Dunne's place on the starting grid and race for him. Evidently Morello wanted to be particularly certain of Martin's win, so he had his men attack Dunne sometime last night. Dunne is alive, but his injuries mean he's in no shape to race, and Tommy is the only person with great driving skills they can find on such short notice. With time running short, Tommy sets up in Dunne's car, and the race is on.
Just as planned, Lichtenberg's car stalls at the start-finish line and he is out of the race. However, there are still many other drivers vying for the winner's cup, and the racing circuit has many difficult turns that can decommission racers if they aren't careful. Against all the odds (Lichtenberg's sabotage notwithstanding), Tommy manages to win the race by the skin of his teeth, and the crowd erupts in a huge cheer.
After the race, Tommy is the man of the hour, celebrating his win with Salieri and the family. During his little victory party, Tommy strikes a sweet rapport with Sarah Marino, the daughter of Salieri's bartender Luigi. After they have their moment, Tommy caps off the evening by finding a thoroughly-sloshed Paulie and driving him home. *
The date is 12 November 1932, and it is closing time for Salieri's Bar. Tommy is about to head home for the night, but the bartender Luigi asks him for a favour. His daughter Sarah has been accosted by a gang of street hoodlums for the last few weeks and he is worried that things may escalate, so he wants Tommy to escort her home tonight. Although reluctant, Sarah agrees, while it is becoming clear to Luigi that her rapport with Tommy is more than just friendship. She grabs a basket of leftover food and leaves the bar as Luigi closes up.
Tommy and Sarah make their way to Sarah's place, making a brief stop to give one of Sarah's neighbours the food basket. Tommy and Sarah spend the rest of the walk joking and flirting with the other, but the fun quickly ends once they find the hooligans lying in wait outside of Sarah's door. The leader of the pack, a fast-talking youth named Billy, puts on his charm and catcalls Sarah. She promptly dismisses him, while Tommy warns the hoodlums about the consequences of hurting the Don's goddaughter. Billy, his right hand Johnny, and the rest of his gang do not take kindly to Sarah's talk nor to Tommy's warning, so they get into a massive brawl.
While Billy tries to "woo" Sarah, Tommy makes quick work of Johnny and his other cronies. However, when he goes to help Sarah fight Billy off, a much larger hoodlum steps out of the woodwork and throws Tommy through a wooden fence. Nonetheless, Tommy manages to sidestep his swings and dispatches him easily. He returns to Sarah as she delivers a well-placed (and well-deserved) knee into Billy's groin, letting Tommy deliver the knockout blow.
Sarah notices some wounds in Tommy's arm as a result of the fight, and she invites him up to her apartment in order to patch him up. As she applies the stitches, she regales Tommy on how she learned to do so from patching her father up whenever her drunken mother would get physical with Luigi. Sarah directs Tommy to spend the night on her couch to rest after his injuries, and takes the time to cuddle up next to him, turning their rapport into an outright romance.
The date is 13 November 1932. Tommy and Paulie are in the meeting room with Don Salieri. Luigi is a close personal friend of the Don and Salieri has treated Sarah effectively like his own daughter, ever since she was a young girl. As such, he is near apoplectic to learn of how Billy and his lackeys forced themselves on her last night. He directs Paulie and Tommy to find these goons and batter them within an inch of their worthless lives.
Paulie and Tommy are provided some baseball bats from Vincenzo. They go to see an information broker named Biff, who runs a pawn shop in Chinatown. He informs them that the street hoodlums can often be found loitering at a derelict service station nearby. The duo head over there and bust open the gates, surprising a few of the hoodlums hanging out. Billy and Johnny recognise Tommy from last night, and they scarper while the mobsters deal with the others. As Tommy and Paulie are pursuing Billy, the hoodlums brandish their guns and the brawling turns into shooting.
As rain begins to fall, Tommy and Paulie fight through the hoodlums in the building and manage to catch up, but Billy and Johnny get into Billy's coupe and drive off, forcing the two mobsters to steal a gentleman's car and drive after them in the rain. The rain has made the roads wet and slippery, but Tommy manages to stay in control and chase down Billy and Johnny until they crash into a support girder.
The crash leaves both hooligans heavily injured but still alive. Tommy and Paulie walk up to finish them off, but Billy pleads for his life when Tommy raises his pistol. Tommy hesitates when he sees the fear and remorse in Billy's eyes, so Paulie shoots him instead and admonishes Tommy for his hesitation. Paulie goes to shoot Johnny but he spends his last bullet, so he declares Johnny dead as well. He steals a packet of cigarettes and tosses them to Tommy, who is staring blankly into the distance and doesn't react at all. With nothing else to do and a lot to think about, they decide to leave before the cops show up.
The date is 20 November 1932, and the mood in Salieri's Bar is tense. Nothing but bad news has come for the Salieri family recently. The Corleone Hotel, a high-class brothel and one of Don Salieri's highest-earning rackets, has switched its loyalties to the Morello family. Billy the street hoodlum was actually the son of prominent city councilor Roberto Ghillotti, and his murder has practically catapulted the councilor onto Morello's side. And to top everything off, Billy's friend Johnny has miraculously survived both the crash and his gunshot wound.
To tie up those loose ends, Salieri decides to target two people in one hit. He assigns Sam to attend Billy's funeral at St Michael's Church and kill Johnny. Meanwhile, Tommy is assigned to kill the Corleone Hotel's manager and bomb the place to spite Morello. Tommy is also ordered to kill a prostitute named Michelle, who works at the Corleone and has informed on the Salieri family in the past. Sam is aghast as Michelle is a regular dalliance of his, and he doesn't believe she should be killed just because she couldn't keep her pillow talk inside the bedroom. He implores Tommy to instead spare her life and ensure that she leaves town.
Tommy reaches the Corleone Hotel and asks around. The manager, Howard Davis, is celebrating his new partnership in the bar lounge, while Michelle is awaiting her clients upstairs. Tommy finds Davis giving a toast to Don Morello in the presence of a small crowd. Posing as another suited gentleman, Tommy walks up as if to shake Davis' hand. Brandishing his pistol, he recites a message that everybody will learn to fear: "Don Salieri sends his regards."
Tommy shoots Davis in the head and the crowd scatters as the Morello gangsters brandish their own guns and open fire. He fights through them to reach Michelle's room and kicks the door open. She initially tries to stave him off, but her thrown vase misses Tommy and he intimidates her by pressing his pistol to her head. In absolute fear, Michelle breaks down and confesses that she gossiped about Sam's secrets with Morello's working girls, never thinking that Don Morello would pick up on it. Satisfied that Michelle knows what it's like to fear for her life, Tommy gives her a wad of cash and orders her to get dressed, leave Lost Heaven, and never return.
After Michelle leaves, Tommy reaches the manager's office and plants his bomb on the underside of the desk. As he turns to leave, he spots a few police officers on street level at the entrance and some more officers in the corridor. The only other way out involves jumping from the office window onto an adjacent fenced roof, separated by the alleyway below. As Tommy considers his choices, the bomb explodes and he instinctively jumps, making it across the gap. Unfortunately, the Lost Heaven Police Department has sent quite a few squads to investigate the assassination, so Tommy encounters a lot of cops gunning for him as he escapes down the rooftops.
Eventually, Tommy reaches St Michael's Church and descends through the bell tower. He has finally broken contact with the cops, but he ends up right in the middle of Billy's funeral service. Billy's family and several of his hoodlum friends have also attended to pay their respects, and Johnny is still alive while Sam is nowhere to be seen. Johnny manages to catch a glimpse of Tommy and the situation turns into yet another gunfight. The priest, for his part, can only watch in horror and beg the combatants to put down their guns.
When the shooting calms down, the priest admonishes Tommy for committing murder in a place of worship, but Tommy dismisses this by pointing out the kind of crooks and creeps that Billy and his cronies were. This allows Johnny to get the drop on Tommy and aim at him while the latter is unarmed. But before Johnny can actually kill Tommy, Sam appears and puts two bullets in the hoodlum's skull. The duo threaten the priest to stay silent about the killings even after he refuses to take money from them.
As they leave, Sam explains that Billy's friends noticed him when he entered the church and chased him out, resulting in him having to shoot them while being unable to bump Johnny off. The mobsters are forced to flee the police officers that have now surrounded the church by commandeering a nearby hearse. Although the day turned out rather messy for both of them, Tommy and Sam escape and return to Salieri's, a job well done.
Norman is flabbergasted that Tommy is confessing to a shootout in a church. He reminds Tommy that he could be convicted at this moment and go to prison for life, but Tommy counters that Norman would never know about Morello then. He recounts that the Salieri family never received any serious attention from the Corleone hit in the following months, while Frank Colletti heard rumours that Don Morello was helping Roberto Ghillotti get re-elected.
The Lost Heaven Police Department occasionally kept an eye on the Salieri family, while Don Morello sensed their waning influence and started encroaching on their rackets. But they were still making good money, and there wasn't really anything else to do in the meantime except to drink with pals and shoot the breeze. That was until Frank stepped in and set their realities straight.
Tommy recalls a story told by Frank, who is scolding him for a barfight the other night. In Frank's childhood, before he and Salieri immigrated to the US, he owned a beautiful Cirneco dell'Etna greyhound. Salieri and Frank set up some greyhound races with the neighbourhood children. They placed bets on the dogs with various trinkets as the prizes, and Frank's dog proved to be unbeatable on the track. However, when Frank's dog went into estrus and out to town, she became pregnant and lost a race. Salieri was furious and tried to drown her, but Frank broke his nose.
Frank outlines that Tommy needs to stop flaunting his riches and think about his career. Paulie can handle himself in a tussle but he isn't so intelligent for anything else, and Sam is fiercely loyal but he isn't so ambitious about his future. Out of everybody, Frank believes that Tommy has the greatest potential to rule Lost Heaven as a worthy successor to Salieri.
1933 — Betrayal
The date is 2 February 1933, and a heavy rainstorm is passing over Lost Heaven. It is late in the evening when Frank calls Tommy over to the bar. He assigns Tommy to help Paulie and Sam secure a regular shipment of bootlegged booze from Canada. A crew is transporting the booze over the border and is scheduled to meet their customers at Copse Farm, just outside the city. Sam is already at the meeting point, so Tommy and Paulie must take some trucks and supervise the loading.
Tommy meets Paulie at the Salieri family's warehouse and they set off together. On the way, Tommy and Paulie talk about Tommy's relationship with Luigi's daughter. Paulie is initially apprehensive, as Luigi was a ruthless hitman in his prime and Sarah undoubtedly knows her fair share about the business from him. However, he believes that Tommy and Sarah will make a good couple and encourages Tommy to marry her.
The trucks arrive at the farm, but it is immediately clear that something is wrong. Sam is not there to greet them, so Tommy and Paulie step out into the rain to look for him. Tommy's search leads him to a truck used by the Canadian crew with a man inside it, who falls out of the truck dead when Tommy opens the driver's door to talk to him. Tommy is then surrounded by several armed men, but he defeats them swiftly.
Paulie arrives after the shootout, along with their compatriots Tony and Donnie. He searches one of the bodies to find a badge, and the men surmise that the rest of the Canadian crew are dead as well. After some investigation, they realise that the men Tommy just killed were officers of the Lost Heaven Border Patrol aligned with Morello. They murdered the Canadians in order to ambush Salieri's men and take the whiskey for themselves.
Tommy and Paulie finally find Sam, who is inside a barn engaging in a shootout with the Border Patrol. Unfortunately, he is shot in the stomach and collapses, so Tommy, Paulie, Tony and Donnie fight through the dirty cops in order to reach him. Once the gunfight ends, Tommy and Paulie rush into the barn to check on Sam. While he's still alive, he is badly injured, so Paulie goes to retrieve a truck to haul Sam out to their mob doctor. Tony and Donnie are ordered to stand guard, but they are quickly gunned down and Tommy is left to defend Sam on his own.
Eventually, Paulie returns with the truck, and Sam is loaded in the back. Unfortunately for the trio, more police cars arrive, and with them is an utter beast of an armoured truck equipped with a machine gun in a turret. Paulie takes it upon himself to drive the truck as Sam dearly clings to life, while Tommy finds a Thompson gun and provides covering fire from the back.
Most of the cops are eventually taken out or left behind, but the armoured truck is still hot on their wheels. Tommy disables the machine gun and shoots away the protective slats on its vision ports. However, his Thompson jams at the last second, forcing him to throw fire bottles into the armoured truck's interior. The officers inside are incinerated and the armoured truck is finally destroyed. After an agonising chase, Paulie, Tommy and Sam finally lose their pursuers and return to Lost Heaven, safe if not sound.
Sam is brought into the doctor's house and Paulie offers to stay with him during his treatment, leaving Tommy to bring the truck back to Salieri's warehouse. He eventually returns to Sarah's apartment, where she initially scolds him for being out so long and missing dinner. However, she soon notices the stunned and exhausted look in Tommy's eyes and the bloodstains on his coat, and grants him some leniency. As Tommy settles, he asks Sarah to marry him, which she agrees to.
The date is 3 April 1933. Tommy meets Don Salieri in a public park, where he has some very solemn news to discuss. Salieri is convinced that there is an informant in the ranks, and he has gone to investigate his account books, looking for someone who hasn't been receiving his fair share as the obvious culprit. However, the books have mysteriously gone missing, yet nobody else should have access to them but his oldest friend and faithful consigliere, Frank Colletti, who Salieri can't reach. The account books contain records of all the Salieri family's transactions, and everybody would earn stints in prison if they were handed to the authorities.
In despair at Frank's apparent betrayal, Salieri assigns Tommy to collect the account books and kill Frank before he leaves town. Vinny provides Tommy with a non-descript car and gives him a lupara to kill Frank with, as is the tradition for those who break the omertà (the Sicilian code of silence). Tommy sets out and asks around town for leads, learning that today has brought a large presence of federal agents in Lost Heaven. Tommy is directed to a safehouse in Oakwood where federal agents have been holding Frank, and he arrives just in time to see the old man escorted into a car. Tommy discreetly follows the car all the way to Lost Heaven Airport, where Frank is scheduled to be flown out of the city.
Tommy finds that the airport is locked down by both Morello gangsters and federal agents, while other motorists and civilians react with equal amounts of complaint and concern. Frank's plane is being readied in a hangar at the far end of the airport, so Tommy works his way through the gunmen that stand in his path. Eventually he enters the hangar and confronts Frank, who is not terribly surprised to see that Tommy has been sent for his head.
Frank explains that Morello had captured his wife March and their daughter Alice, offering a deal to spare their lives and allow them to leave the country. In exchange, he would attain Salieri's account books to turn over to the federal authorities, leaving him free to swoop in on Salieri's territory. Frank grants Tommy the key to a safety deposit box within the vault of the Grand Imperial Bank. He has stashed the books there beforehand, and he would have given the key to Morello if Tommy hadn't found him first.
Tommy gives a wad of cash to the Colletti family's pilot, and Alice and March reluctantly board the plane at Frank's insistence. Tommy asks Frank how he could betray the Salieri family or why he wouldn't go to them for help. Frank explains that he's grown exhausted with the family and his criminal life over the years, figuring that, for one reason or the next, Salieri would one day order his death. Morello's kidnapping of his family was just the straw that broke the camel's back. As the pilot starts his plane, Tommy readies his lupara and prepares to silence Salieri's ex-right-hand man for good. However, upon seeing March and Alice cowering in the plane, Tommy finds himself unable to murder Frank in front of his family. He allows Frank to board the plane and leave for better pastures with his loved ones.
Tommy goes to the Grand Imperial Bank shortly afterwards and retrieves the books. To cover his tracks, he obtains some gasoline and burns Frank's house to the ground. Some time later, the funeral for the "late" Colletti family is attended by both the Salieri and Morello families, including Marcu Morello himself and his brother Sergio. Don Salieri and Don Morello mourn side-by-side at Frank's "grave", standing together for the first time in a long while. Aside from that, Salieri is satisfied with Tommy's work and never asks any questions. In fact, he seems to be unwilling to talk about Frank ever again.
The date is 31 August 1933, and Salieri and Tommy are in the middle-class neighbourhood of Oakwood. As Morello was unable to attain Salieri's account books, Councilor Ghillotti has turned to a crooked prosecutor named Archibald Watkins to convict Salieri for Billy's murder. So far, Watkins has secured witnesses and evidence to help bolster the case. Sam and Paulie have been dispatched to handle these witnesses, while Tommy is being sent to the affluent neighbourhood of Beech Hill in order to break into Watkins' mansion and retrieve the evidence in his safe.
Tommy is no safecracker, of course, so Salieri is taking Tommy to meet with their associate, an expert locksmith named Salvatore who has recently immigrated from Italy. Salieri leaves Tommy to drive Salvatore to the mansion, but Tommy soon realizes an issue that may arise with this plan; Salvatore only speaks a small amount of English, and Tommy speaks even less Italian. Cracking safes is delicate enough, but vaulting a language barrier at the same time will make the operation even harder. In spite of these communication differences, Tommy and Salvatore resolve to work together.
They sneak into the prosecutor's mansion through the hedge maze and manage to find the safe, hidden behind a painting in Watkins' office. However, while Salvatore is busy with cracking the safe, Tommy sees a car pulling into the driveway as Watkins is returning home, and he urges the locksmith to hurry. When the safe is finally opened, Tommy immediately goes to retrieve the evidence inside — only to end up triggering the alarm, alerting the guards and forcing the duo into a shootout.
In spite of the best efforts of Watkins' security, Tommy is able to steal one of his cars and drive Salvatore out of the mansion. After they elude the police response, Salvatore begins a scathing rant in Italian imploring Tommy never to do anything so careless again. Unsure what to make of anything his partner just said, Tommy carries on driving and drops Salvatore off at his house. With that, Salieri's operation is safe for now.
The date is 22 September 1933, and Salieri is looming over his prospects as his men load the last of his illicit booze into a truck. The bootlegging racket has started to dry up for the Salieri family, so their liquor stocks have been gradually sold off to make ends meet. However, Paulie hasn't given up hope, and he believes he has found a way to secure more.
While having his usual fun at the Blue Tropics brothel, Paulie overheard another customer complaining about a business opportunity that was screwing him over. The sour-faced fellow turned out to be a gentleman from Kentucky named William Gates, whose father runs a profitable distillery. He has gone into the bootlegging business with Morello, but the Don has been enforcing much harsher terms than Gates would prefer, even breaking his nose to make his point. To make a long story short, Gates is convinced to work with the Salieri family, and today he is scheduled to meet them at a parking garage in the city.
Paulie plans to mask the operation by making it look like Gates was robbed, thus putting the blame on Morello for not being able to protect him and thus get out of business with him. As the cherry on top, Gates is providing genuine high-quality whiskey as opposed to moonshine, which would provide less of the latter's health risks and likely a justified upcharge for their customers. With literally no other ideas or choices, Salieri assigns Tommy, Paulie and Sam to meet Gates at the parking garage and set up the whiskey deal. Salieri's bodyguard Carlo is also going along, although he is strangely apprehensive about the potential for trouble if Morello finds out.
Gates' new customers arrive at the meeting point and Tommy tests out his whiskey. Satisfied with the taste, he places a wad of cash in Gates' hand with an offer of more supply runs in the future. Paulie punches Gates' bruised nose, which initially alarms Tommy and the others, but both of them clarify that it's only to make the robbery guise look convincing. The deal goes well and the Salieri mobsters are gloating about all the money they will earn — just as Tommy hears a screeching of tires, and a car full of Morello goons charges onto the parking garage floor. The goons open fire and neutralize some of Gates' crew, but Tommy and his compatriots manage to soundly defeat them in turn.
After the ambush is cleared, Paulie checks on Gates. Thankfully he is alive, but the gunfight has left him with a bullet in his shoulder. He urges the Salieri crew to take his truck loaded with whiskey and get out, while the rest of his men extract him. Anticipating that Morello will be sending more gunmen to get the whiskey back, Sam and Carlo drive the truck while Paulie and Tommy scout ahead.
Sam's instincts turn out to be correct, as Tommy and Paulie fight through more of Morello's henchmen as they descend through the parking garage. At one point, one car crashes and bursts into flames, creating an impassable wall of fire which Tommy puts out by turning on the sprinkler system. Once the crew is at street level, Tommy and Paulie hop into a nearby car and drive alongside the whiskey truck, defending it from even more Morello triggermen.
Thanks to Sam's own driving skill, the Salieri crew eventually shake their pursuers and return to the warehouse. Salieri is thrilled to see the booze in his possession, and the taste of it gives him confidence that such quality liquor will ease their financial woes. He, Tommy, and the rest of the crew celebrate their success with a toast.
Tommy recalls that the Salieri family was finally back on its feet again thanks to their new supplier. However, a little over two months later, the 21st Amendment was ratified into the Constitution, repealing Prohibition and making alcohol rackets practically worthless. But Don Salieri saw the opportunity to start reclaiming territory from Morello, and the money they did earn was invested into new rackets like construction and gambling. The Salieri family was making steady profits, Tommy married Sarah and had a daughter, and Sam and Paulie were in charge of some rackets of their own.
Detective Norman reveals that a high court judge was arrested on child solicitation charges a few years ago. Once in the courtroom, he confessed to taking kickbacks from both the Morello and Salieri families, pitting them against each other to get a better deal from either of them. Tommy is left aghast as he makes the connection, explaining that while Salieri and Morello had always been fighting before, they usually never tried to start an all-out war. When Don Morello learned that the Salieri family was back on its feet and poised to conquer, it was the final straw that pushed him into trying to take out the competition first.
1935 — The War
The date is 1 May 1935, and today is as ordinary as any other. Don Salieri wants to go to Pepé's Restaurant for lunch, but Carlo has called in sick today, so he asks Tommy to drive him there instead. He spends the journey in an optimistic mood, revelling in all the new high-level associates he is doing business with these days. Meanwhile, Tommy has been promoted to the rank of capo for his loyal service to the Salieri mob, but he still finds time to hang out with Paulie and Sam.
When they arrive at the restaurant, Don Salieri is heartily welcomed by its owner Pepé, a delightful old fellow who takes pride in his little eatery. He seats Salieri and Tommy at a table and serves them a delicious caponata, bringing a fine chianti wine to go with it. Tommy declines the wine, explaining that Sarah threatened to leave him if he didn't become sober. Salieri is glad to hear the news... primarily because he himself put Sarah up to the ultimatum in order to ensure that Tommy did not make any mistakes that could cost the Salieri family.
Tommy gets little time to ruminate on this news when Pepé arrives with their food, and doesn't even get time to taste it when cars pull up outside the restaurant and drop off men armed with Thompsons. Tommy tips over the table and gets Salieri behind it just as the men open fire, mowing down unfortunate customers and staff in an attempt to kill Salieri. Tommy deduces that this is Morello's doing, and manages to keep Salieri from death as the Morello footsoldiers cap off their attack by tossing a grenade into the restaurant.
The explosion blows out the windows and starts a fire, while Tommy and Salieri are now hiding behind the bar counter. Alive as they may be, both Tommy and Salieri know attempting to fight their attackers head-on would be suicide. As such, Salieri orders Tommy to escape through the back door and flank the shooters while he distracts them with a nearby shotgun. It is a hard fight, but Tommy manages to neutralize all the gunmen and save the Don's life. Tommy offers to take the Don back to his bar, but a furious Salieri has a different destination in mind: Carlo's place.
Salieri concludes that it's all too much of a coincidence. An attempt on his life was made soon after Carlo called in sick, while he knew where the Don would be heading today. Salieri figures that Carlo has turned to giving information to Morello, and he has likely been going behind his back for a long while. Tommy realises that Carlo's snitching would explain why he was so twitchy during the whiskey deal with Gates, and why the Salieri family was ambushed at Copse Farm as well as so many other troubles in the past few years.
Tommy drives Salieri to Carlo's apartment in Holbrook, where he is having himself a swell time with a woman. Salieri lays a heavy beating on his soon-to-be-ex-bodyguard, but his age exhausts him quickly enough that Carlo gets an opportunity to make a run for it. Tommy follows close behind, chasing Carlo down the fire escape and through the apartment courtyards, while Carlo pathetically begs for his life. As he is climbing a ladder to get away, Tommy puts a bullet in him, which gives Salieri the chance to catch up and stomp Carlo's head into a fine red paste.
Some time later, Sergio Morello comes to talk to his brother as he is laying a beating on a man planning to organize a labor strike at the docks. The chipper mood Marcu is in quickly fades when Sergio informs him that Salieri survived the assassination attempt and Carlo was found dead, his head smashed like a watermelon. He flies into a rage and murders the poor union sod when his muffled begging sets him off further. Don Morello tells his brother to keep safe and prepare for trouble, as a state of open war now exists between the Salieri and Morello crime families.
The date is 2 May 1935, and Don Salieri is hatching a plan to dismantle the Morello family for good, starting with killing off Morello's best allies. Today is the fiftieth birthday of Roberto Ghillotti, the city councilor who has been causing the Salieri family so much trouble, and he is celebrating with a lavish party onboard the paddle steamer Lost Heaven Queen.
Ghillotti is still vindictive about the murder of his son three years ago, so he'll never turn on Don Morello, which is why Don Salieri plans to kill him instead. He assigns Tommy to board the steamboat and assassinate Ghillotti in public. Morello's security assigned to protect the councilor will be searching everyone on board for weapons, so Tommy's goal is to locate a revolver stashed by the crew's janitor (who is on Salieri's payroll) and use it to end the councilor's life.
Arriving at the dock where the Lost Heaven Queen is letting guests on, Tommy locates Sam in the crowd. Sam explains that he and Paulie have found a newly-hired sailor and knocked him unconscious in a nearby bathroom stall. This will allow Tommy to take the crewman's uniform and disguise himself on the ship until they are far enough from land for the assassination.
After the task is complete, Sam and Paulie will arrive in a speedboat to pick Tommy up. They will be signalled by the fireworks display that is rigged to begin after Roberto ends his big speech, which will double as Tommy's cue to pull the trigger. Tommy boards the vessel and it departs Lost Heaven, while Paulie and Sam watch from the docks.
After pretending to go about his job for a while, Tommy finds the janitor half-drunk in the engine room, who reveals that the revolver is stashed in a restroom on the ship's stern. Tommy goes to find the gun, but on the way he encounters another sailor who recognizes him as one of Salieri's men. Dispatching the other sailor easily, he manages to find the revolver behind the toilet. Then Tommy sneaks through the wheelhouse to a vantage point on the promenade roof, overlooking a podium where Ghillotti is due to give his speech.
Soon after, the councilor appears on the deck and steps onto the podium to speak. He gives a rousing speech to his guests about how he will ensure the end of organized crime in Lost Heaven (or at the least, the kind of organized crime he has a personal vendetta with). With his speech reaching its close, Tommy opens fire as the firework show begins, putting an end to 50 years of Roberto Ghillotti. As soon as Ghillotti falls dead, panic spreads aboard the ship and civilians run for cover. Tommy fights his way through Ghillotti's bodyguards down to the lower decks of the Lost Heaven Queen, where Paulie and Sam arrive in their speedboat. Tommy jumps aboard and the trio sail off into the night.
Don Salieri and his men have turned their sights onto Morello's brother and underboss Sergio. On the night of 12 May 1935, Sam and Vinny have found Sergio and are engaging in a car chase with him. Vinny aims his pistol for a fatal shot through Sergio's head, but Sergio is jolted out of the way and the bullet goes through his windscreen instead. Then the cars approach a railroad crossing with an oncoming train bearing down on them. Sam manages to get across just in time, but a tire bursts and their car spins out into a tree. Sam and Vinny are left in the dust to curse Sergio's ungodly lucky streak, while Sergio smugly drives away.
Sergio Morello has an infamous propensity for incredible luck, and many have tried to assassinate him and failed before. The date is now 13 May, and Salieri is assigning Tommy to fulfil the difficult task of eliminating him. Vinny fashions a bomb for Tommy to attach to Sergio's car, which will detonate when he starts it up. Tommy drives out to Sergio's house in Oakwood and secures the bomb with no trouble.
He waits at a nearby phone booth to watch what happens, calling Sarah in the meantime. To Tommy's horror, however, it is Sergio's mistress who gets in the car instead. Tommy desperately runs out to stop her, but he is too late, and she is incinerated in mere seconds. Tommy calls Vinny in a panic to explain how the plan has gone wrong, and the gunrunner brings him news that brings some minute comfort; Paulie and Sam have found Sergio at a diner not far from the house.
Tommy arrives at the diner and is given a Thompson by Paulie. He and Sam notice that Tommy is still shaken, but must put it aside for the sake of the mission. The gangsters kick open the diner's door ready to shoot, only for Sergio to take a waitress hostage. Still rattled over having murdered an innocent woman, Tommy thwarts Paulie's attempt to shoot their target through the waitress. This leaves Salieri's men to shoot through Sergio's guards and allow him to escape through the back door into a waiting car. Fortunately, a nearby motorcycle allows Tommy to catch up and pursue him. Paulie and Sam attempt to catch up in a car, but Sam spins it out, leaving Tommy to chase Sergio on his own. Eventually, the chase takes both of them all the way to Lost Heaven Harbour.
Tommy shoots his way through dozens of Sergio's henchmen, leading him to a train depot Sergio has holed up in. Tommy manages to use the location against Sergio, releasing the brakes on a nearby train car and using it as a battering ram to force open the building's heavy doors. Once the last of Sergio's goons are all dead, Tommy finds Sergio himself and manages a lucky shot, following him to a nearby room filled with fuel barrels.
When Tommy finally has him cornered, Sergio tries to fire back at Tommy only to find his gun out of bullets. Tommy lines up his killing shot... only to find he's run out of ammunition too. Sergio mocks Tommy, claiming that nobody can touch him. Tommy calls him on his luck, dropping a lighter into a puddle of spilled oil where Sergio lies. The fire works through Sergio, and Tommy manages to escape the building before the fuel explodes, putting an end to Sergio's lucky streak.
The date is 20 May 1935. The death of Sergio Morello has brought the Salieri-Morello war to a fever pitch. Don Marcu Morello himself has wisely kept to the background, but today he is due to attend a charity gala at the local theater in order to keep up appearances. Salieri instructs Tommy, Sam, and Paulie to drive to the theater and gun Morello down as he leaves. The assassination of a respected Don among the city's elite is meant to send a message; no matter how much money or how many connections a person may have, anyone who dares to cross Don Salieri will die all the same.
Vinny provides the trio with some Thompsons, and they set off. They are enthralled in a sense of excited catharsis as they wonder what will happen after, and where the Salieri family will venture next. Sam, for his part, believes that the Don will not mourn Morello's death and may even change as a person after he takes full control of Lost Heaven.
They reach the theater, only to find Morello already on his way out. He hurries into his silver limousine as Paulie opens fire. A passing truck prevents the trio from getting a clear shot, forcing Tommy to put the pedal to the metal and chase Morello through the city. Along the way, Paulie and Sam turn their sights on Morello's backup in the form of his gangsters and the Lost Heaven Police Department. The chase eventually leads them to Lost Heaven Airport, where Tommy, Sam, and Paulie exit their car and chase Morello down on foot.
Shooting through dozens of Morello's remaining footsoldiers, the trio eventually reach a hangar where Morello's personal plane is getting readied, waiting for him to leave the city. Thinking quickly, Tommy gets into the passenger seat of a nearby car while Paulie drives down the runway. As the plane takes off, Tommy uses a Thompson gun to destroy the engines. This ensures that the plane's aerodynamic capabilites are incapacitated, and it cannot stay in the air for much longer. The Salieri gangsters follow Morello's plane as it belches smoke over the city. Eventually, the plane falls out of control and crashes, and the trio hurry to the crash site to ensure that Morello stays dead.
Checking the wreckage, they find Morello still alive, but in a burnt and agonied state. Paulie comments that Morello is surely dead, just unaware of it yet. Tommy lets the Don know by firing a volley of Thompson rounds into his body. The Salieri-Morello war is at its close, and with it, Ennio Salieri has secured his place as the Don of Lost Heaven. In his office, Salieri looks over a picture of him and Morello in their younger days, alongside their old boss Don Peppone. Raising a glass to his former friend, he tells him that he will see him soon on the other side.
Norman is shocked to see that Don Morello's killer, whom he has been chasing for three years, is sitting right in front of him. He talks of how Tommy will see life in prison, if not outright execution for this. Tommy counters that the man who killed Morello isn't nearly as important as the man who ordered the assassination. He offers to help Norman put away Don Salieri in exchange for the safety of his family. As his ace in the hole, he will give Norman the account books he got from Frank to make the evidence truly stick.
Norman takes out an old photo of three men from his case files. Tommy doesn't recognise the people at first, until Norman explains to him that the older gentleman is Don Felice Peppone, while the two younger men are his capos Marcu Morello and Ennio Salieri. What's more, the photo was taken at Morello's wedding in April 1920, where Salieri was the best man. Some time later, Don Peppone died in 1922 (whether he drowned or was murdered depends on who you ask), and Salieri and Morello agreed to divide Lost Heaven to keep things running smoothly.
Tommy is surprised, as he never knew that Salieri and Morello were once best friends before they became bitter rivals. He recounts that after Morello's death, Don Salieri was ecstatic at finally ruling over the whole of Lost Heaven. However, Tommy thought over what had happened in the last few years, and he came to a terrifying epiphany: if a lowly cabbie like him was able to end a powerful Don, then all of Morello's wealth and power had given him only one sure thing — a great big target directly on his forehead.
Although Tommy tried to downplay the ramifications as best he could, he eventually started sensing a target on his own head too. Eventually, Tommy started to wonder if even Sam and Paulie may have been getting ambitious enough to turn on him for their own gain. He concludes that beneath all the talk about loyalty and honour, organized crime is a competitive business, and even a gangster's truest friend is capable of betraying him.
1938 — Leaving It Behind
The date is 15 July 1938. Tommy comes up to Salieri's meeting room, giving the mob's dues to his boss. Salieri notices that Paulie's contribution seems like it is missing some money, but Tommy explains that he has put more money into his own payment to cover for Paulie being short. Salieri tells Tommy a story about two friends who went swimming in a lake one day. One friend swam too far out and began to sink, and when the other went to save him, the first one drowned both of them in a panic. He explains the moral of this story succinctly: don't try to save your friends from their own mistakes.
Salieri then turns Tommy's focus into the latest thorn in his side: the Illinois gubernatorial elections are approaching, and candidate Hank Turnbull is campaigning on a platform of bringing down organized crime. Tommy finds this quite laughable due to Turnbull spending a fortune on prostitutes, but Salieri sees Turnbull as a genuine threat. Trying to put the politician on their payroll would be futile, so Salieri assigns Tommy to assassinate him. Turnbull is planning a political rally today in Robinson Park, a location which is far too open and exposed to attack head on. Instead, Tommy will enter the abandoned prison on Central Island, make his way to a guard tower, and use a planted sniper rifle for the assassination.
Tommy goes to Vinny to receive a key to the old prison. Vinny informs Tommy that the place is now filled with homeless squatters, which may complicate matters. When Tommy arrives at the building, he is encountered by one of the vagrants. The vagrant explains that he was paid to mark the way to the guard tower with a certain sign. All Tommy must do is follow the signs, and he'll be where he needs to go. Tommy enters through the sewers, following the signs and flipping gate switches whenever he needs to. Some of the other squatters do not take well to Tommy's presence, but they prove little challenge to the mobster.
Finally, Tommy reaches the tower and the rifle. When Turnbull makes his appearance, Tommy takes his shot and the hopeful governor falls dead. Unfortunately, as Tommy turns to leave, the floor gives way and falls, taking him with it and knocking him out cold. By the time he comes to, the Lost Heaven Police Department has made it to the prison, very incensed and out for his blood. The squatters provide some distraction for Tommy to slip by, but he is eventually discovered and forced to shoot his way out. Once at street level, he steals a car and flees with practically every police officer in the city looking for him. It is a challenge, but at last Tommy manages to elude his pursuers and returns home.
The next day, Tommy goes into the kitchen for his morning coffee as Sarah reads a newspaper describing Turnbull's assassination. Tommy brings up Turnbull's hypocrisy, but Sarah counters that Turnbull will be most remembered for his efforts to ratify the 19th Amendment and grant women the right to vote, a move that risked his entire political career. Tommy starts to feel pangs of guilt over listening to Salieri as Sarah advises him not to do things he will be remembered poorly for.
The date is 30 September 1938. Tommy, Sam, Paulie and Don Salieri are in the meeting room, trying out some cigars. Salieri explains that the federal government has seized a large shipment of Cameroon cigars for inspection, and it's the job of the trio to get into the impound yard and steal them. Tommy voices that stealing a shipment of cigars, even quality ones like these, seems rather small-time for the Don. Salieri congratulates Tommy for his keen mind and clarifies that the cigars are a cover for a shipment of stolen diamonds, and that is the real prize for the team. Sam explains to his friends that they will silently infiltrate the harbour by stealing a customs truck and some uniforms, then slip away with the loot with nobody the wiser, but Tommy still feels something is sketchy about this job.
As the mobsters make their way to the impound, Tommy grows uneasy of Paulie waving his pistol around. Paulie explains that he is just nervous, because for the past few weeks, he has been casing the Grand Imperial Bank and planning to rob it. Paulie offers to let Tommy and Sam in on the job but both of them have their doubts. Tommy figures a bank heist is far out of their league while Sam notes that Salieri would never sign off on it. Paulie offers that they don't let the Don in on the heist (or at least not until after the fact), but his friends figure it's far too much of a risk.
Arriving at the impound, Tommy is sent to find the truck and deliver it to Sam and Paulie while they look for uniforms and the paperwork of a driver. Tommy finds a truck with no real issue, but Sam and Paulie are only able to find two uniforms for themselves, forcing Tommy to stay hidden in the back. The three drive the truck to the impound gate and are let in, only to find out the place is guarded heavier than they were expecting. Paulie and Sam are roped into following a dock worker to maintain their cover, leaving Tommy to find the cigars himself. Checking through various records, Tommy manages to slip into the impound and locate the crates they need.
After Paulie and Sam knock out their escort, they load the crates alongside Tommy and prepare to leave. Unfortunately, an alarm rings out in the building, and the police set up roadblocks to catch the truck. Luckily, Tommy manages to weave through the backstreets and eludes them, leaving the crew to drive to Salieri's warehouse and unload the boxes.
Upon arrival, Paulie informs the guys that one of the crates holding the cigars was damaged by gunfire during the escape, so Tommy takes it upon himself to check on the cigars. However, upon searching through a box, he comes upon a nasty surprise: hidden inside is not diamonds, but a packet of black tar heroin. Tommy figures that there were never any diamonds, and the heroin was the true prize that Salieri was after. The Don himself soon arrives, and Sam convinces Tommy and Paulie to keep their cool and let Salieri think they don't know. Salieri lets the crew go for the night as his men unload the boxes, instructing Sam to drive him back to the bar. Paulie and Tommy opt to take the elevated train home.
Once the Don is well out of earshot, Paulie lets loose with his frustrations. Salieri not only went back on his previous beliefs that dealing in hard drugs was a line he wouldn't cross, but he risked all three of them dying in prison if they had been caught. The fact that Salieri left them in the dark about all of this is pushing Paulie to his breaking point.
As an elderly gentleman boards the train, Paulie reflects on his gangster career. He is approaching his midlife with no wife and no kids, and only has his criminal record to show for it. For all his scheming and ambition, he has barely advanced from when he first joined the Salieri family, and he has realized that he won't have any more chances now. He can feel his age catching up with him, and between the Don's same boring stories about the old days and the constant random violence, he is just about ready to end himself.
The heroin discovery is the final straw cementing in Paulie that he is going to rob that bank come hell or high water, whether Salieri approves or not. With this last score, Paulie hopes to get enough cash to finally retire from the mobster life and maybe open a small business for himself. Listening to Paulie reminds Tommy of exactly why Frank was tired of his criminal life, and why he did what he did for himself. Angered at Salieri's blatant deception, he fully supports Paulie's bank robbery idea, and they plan to do it together.
The date is 3 November 1938. Tommy and Paulie are outside the Grand Imperial Bank, going over the plan one final time. Paulie will use his Thompson gun to control the crowd in the lobby. Meanwhile, Tommy will use his shotgun to force the manager to open the vault.
The two gangsters begin their assault like clockwork. Paulie knocks out the guard in the lobby and fires a few bursts to make the civilians compliant, while Tommy goes upstairs to find the manager's office. While Paulie keeps the civilians in check, Tommy bursts in and forces the man down to the vault at gunpoint. Tommy is told that there is only a single guard in the vault, so he tells the manager to order him to lower his weapon once they are in there.
The manager is brought to the vault, where he pleads with the lone guard to put down his gun — only to run off after bluffing Tommy into an ambush. Suddenly, Tommy is beset by not one but three security guards, who pop out from behind the walls ready to protect their cash stocks. Still, three security guards are no match for Tommy, who promptly gets the vault key from the manager when he's through with them.
Tommy heaves the vault door open and fills a nearby bag with as much money as he can. The cops arrive shortly after, and Paulie runs down to the basement. He grabs onto the bag while Tommy handles the officers storming into the vault. As they return to the ground floor, the swarm of police officers at the front entrance forces Tommy and Paulie to flee through the back door and hop into a nearby car.
With almost the entire Lost Heaven Police Department laying into them, Paulie and Tommy drive off. After a long chase, the cops finally lose sight of the duo, allowing them to store the car in the Palermo Club, which Sam has owned ever since the end of Prohibition. Tommy and Paulie are stunned to believe they have actually pulled the heist off, and they take swigs from a flask in celebration. The duo plan to meet at Paulie's apartment soon to divide their bounty, glad to finally be free of the Salieri mob.
The date is 4 November 1938. Tommy enters the kitchen of his house as Sarah ribs him for his fitful sleep the night before. Tommy claims himself to be fine, then tells Sarah that they should take a trip out of town. He explains that he and Paulie have come into some money, and they should use some of it to go on a nice trip. Sarah is rather suspicious of this sudden windfall, taking special note of how on edge Tommy is. Still, she sends him on his way.
Tommy reaches Paulie's place, only to find the door ajar. He enters with his gun drawn, and his fears are confirmed: Paulie has been shot dead. Even worse, in a frantic search through Paulie's apartment, Tommy cannot find the heist money anywhere. He finds Paulie's telephone ringing and anxiously picks up the receiver. Sam is on the other end, and he seems just as despaired when Tommy tells him what's going on. Sam explains that Salieri has discovered Paulie and Tommy robbed the Grand Imperial, and will not stand for it. Now Paulie is dead and Tommy has a price on his head. The two agree Tommy needs to skip town immediately. Sam agrees to meet Tommy at the Lost Heaven Art Gallery to get him some money to ensure his family's safety. Tommy reluctantly leaves his friend's body behind.
Upon arriving at the gallery, Tommy is accosted by two men with guns trained on him. Sam appears above on a balcony. He says that Tommy and Paulie have put him in a difficult situation, then tosses wads of cash down, snidely calling it Tommy's "cut". Tommy realizes that Sam himself killed Paulie and took the heist money, and he has just led him into an ambush. Sam explains that doing this will truly get him into Salieri's good graces, and the fact that Sam now has the entirety of the bank score to himself doesn't hurt matters. Besides, the Don is already mad at Tommy for another reason: he has learned that Tommy spared both Michelle and Frank's lives, disobeying direct orders. Tommy counters that his former friend isn't trying to kill him out of loyalty of the Don, but rather out of fear for his life. Sam leaves Tommy to be shot by his gunmen, but Tommy manages to maneuver out of the situation and get into cover.
A swarm of Salieri mobsters are sent to kill Tommy under Sam's orders, but like so many times before, Tommy shoots his way through them, destroying much of the gallery in the process of hunting Sam down. It is a rough fight, but Tommy manages to catch up to Sam and corners him on the balcony above the atrium. As Sam lies injured, he offers to let Tommy escape if he spares his life. Noting the hypocrisy of the situation, Tommy balks at the offer, even as Sam says that Don Salieri will never stop hunting him if he leaves this building.
Tommy asks how Frank got found out, and Sam attributes it to Frank's own stupidity. After the Colletti family landed in Italy, Frank initially laid low, but his love of the dog tracks led him to spend enough time there that one of Salieri's associates there spotted him. The Don soon sent men there to permanently put Frank down (and likely his family along with him). Tommy hesitates to shoot Sam again, which he remarks is Tommy's own weakness. Sam tries to recall a fond memory with Tommy, but the mention of Paulie's name gives Tommy the push he needs to finish him off. Tommy leaves the gallery, and with it his life behind, as Sam's blood drips onto the atrium floor amongst the money.
With Tommy's story brought up to the present, Detective Norman fully understands his situation and expresses his volition to help the former mobster. However, he cannot truly do anything for Tommy or his family unless Tommy testifies against all his former friends in court, which he feels Tommy does not have the guts for. The fact that he doesn't guarantee safety for Sarah or their daughter nearly drives Tommy to storm out of the diner.
Norman stops him, however, clarifying that as a husband and father, he does understand why Tommy even approached him. His issue is that a trial of such a large criminal organisation would be a lengthy and historic affair, and the authorities may not be able to afford much protection for the entirety. There are few officers in Lost Heaven that Norman trusts, and if it comes down to him or Tommy possibly being murdered, he will not make his own wife a widow. Even then, Tommy has still committed various crimes over the past eight years, so prioritising his safety won't be the first thing on anyone's mind.
Tommy tries to sweeten the deal by reminding Norman that this case would not only let him finally solve the murder of Don Morello, it would bring down an entire criminal syndicate. Whether Tommy lives or dies, the arrest of Salieri and his mob would cement Detective Norman's legacy in the history of organized crime. Norman counters that he is only here to put Salieri behind bars, so he will keep Tommy safe as long as Tommy helps him. With that, the two men confirm their deal.
Epilogue
The trial of Ennio Salieri and his mob makes headlines all across the United States. Thanks to Tommy's testimony, a great many mobsters and associates are jailed, while Salieri himself is sentenced to life imprisonment. For his part, Tommy serves 8 years in prison; while he initially finds the solitary environment difficult to adjust to, he manages to compose himself while he waits to come home. Meanwhile, the Angelo family is placed in witness protection and relocated to Greenfield in Empire Bay. They live out their new lives in relative comfort, and Tommy proudly watches his daughter get married as he grows older.
On 25 September 1951, Tommy is watering his lawn as a red car pulls up near his house. Tommy goes about his business until he hears two particular words.
"Mr. Angelo?"
Tommy turns to see two men on his lawn. The mention of his true name signals to Tommy that he has finally been found by Salieri, and his time has come. He turns to the speaker, a young man named Vito, and confirms he is who they're looking for. Vito recites a message to the ex-mobster, one that Tommy knows all too well.
"Mr. Salieri sends his regards."
Vito's heavier-set companion brandishes a lupara and blasts Tommy directly in the chest. As the two mobsters drive off to settle their own issues, Sarah and the rest of Tommy's family rush onto the lawn to attend to him. Tommy advises them not to worry, as his death now means the rest of them are safe from Salieri's wrath. As he dies surrounded by the family he loves, he thinks of a lesson he has learned from all this: there are many things in this world that will only be with you for so long, and the only truly eternal thing is family.
