You Lucky Bastard is the 16th mission in Mafia: The City of Lost Heaven.
After the previous assassination, Don Salieri has the next target to remove in order to bring down the Morello family: Sergio Morello Jr.. His plan is to have Paulie assassinate him at his favorite restaurant. All Tommy has to do is drive Paulie to the restaurant on Central Island.
After the cutscene, go see Vincenzo. He will give you a Colt 1911 and he gives Paulie a Tommy gun. After you collect your guns, go see Ralph. He will show you how to open up a Guardian Terraplane. Once opened, get Paulie and drive out.
Attempt 1: Italian Garden Restaurant
After you have left, drive to the location on the map. Once there, park the car and get out wait for Paulie to tell you what to do. Then walk into the phone booth and make the call. A cut scene will play and shows what happens, Tommy making the call and asking for Sergio and instead one of his random goons will answer and say he isn't there today. Paulie not realizing it, kills the guy with Tommy telling him its not him. After the cut scene is over, get in the car and drive away while trying to lose your tail. After the tail is lost, drive back to Salieri's Bar.
Attempt 2: Sergio's car outside his home in Oakwood
Salieri says he has another idea to rub out Sergio. He has learned from Big Biff that Sergio has a mistress in Oakwood. The plan is plant the bomb underneath his car and wait for him to turn the car on to blow it up. Grab a car and drive to the location on the map. When you get there, you will see Sergio's car and beside it is a guard. Wait for him to go inside and then go up to the car and hit the interact button where it will show Tommy planting the bomb. Once the bomb is planted, walk away down the street. A cut scene will play showing the bomb go off, only showing its Sergio's mistress who dies in the bomb blast.
Attempt 3: Rainbow Garden Restaurant
After a cut scene, drive to the location on the map. After this a cut scene will play. In it, Sergio is talking to a few of his men and then notices Paulie. Paulie tries firing his Thompson only to have it jam. After the cut scene is over, wait for Paulie to get in the car and drive back to the bar.
Attempt 4 and chase Sergio
In the cut scene, Tommy explains that after so many failed attempts, Don Salieri offered the job to other members of the family while Tommy went along as he describes as an "insurance policy". After a crew who's plan was to have Sergio's new car with him and his driver in it, to get stuck on the train tracks and have them run down by a train on standby. After sometime, Morello arrives. The crew is in position and ready only Sergio notices somethings wrong and as sure as he knows, makes his driver get off the tracks leaving the crew in the car run over. After this, drive after Sergio and when he gets to his destination, you'll start the next part of the mission.
Alright, use the car as cover and take out all of the guys here, then take out the dudes in the truck that just drove up. Then, move over to the building with a guy with a Pump-action Shotgun in the little window thing. Take him out then kill the guy who comes running. Now, go into the building and take out the guy who doesn't even notice you until you're 2 feet behind him. Exit the building and head over to the train. Now, take out all of the guy's hiding behind the train and use the first aid kit on the wall of the building by the train if needed. Also, there's grenades here behind one of the trains. Go back to where you started and take a car, any car,and drive over to those red towers. There's two guys up there with rifles, but they can't hit you when you're in the truck, really. Alright, now. Look for this white barrel looking thing next to the ship, sort of by the red tower. It should even have a symbol that warns you it could blow up painted on it. It's pretty big, so you can't miss it. Now, stay in the car and pull out a hand gun and position yourself FAR AWAY from the barrel. Now, shoot at the barrel and it will blow up. You just killed four guys. The two guys in the red towers and the two guys hiding behind the crates with Tommy guns. Now, take out the other guy with a rifle hiding in the building across from here, sort of by the oil tankers by the tracks. Then go in. Look around inside a little and you'll find a first aid kit. Save it for later unless your health is very low.
Now, there's still some guys on the left outside of this building, take them out. Walk over to those gas tankers I mentioned a bit ago, located on the tracks. Now, pull that lever by them and then walk over to the left side of the front oil tanker. There is a ramp-like piece of metal holding the train's front wheel in place. Click the action button and it will be removed. If you don't see it, just run around that tanker while clicking the action button. When you finally get it, the tanker will go barreling down the tracks. Then walk over to the door that it just hit. It'll trigger a scene. In it, Sergio will be sending you insults while the tanker is leaking. Tommy notices this and throws his lit cigarette at it causing it to explode. Before going into the action, you may need to patch up. If this is the case, go past the burning tank until you see a building labelled "Hall 2", to your left there will be another one with a ramp and a blue door. Go in through the blue door and grab the first aid kit to your left. Now go back to the scene and enter the breached building.
Kill Sergio Morello, Jr.
Take out all of these guys in here. They'll come to you. However, a few of them will still remain hidden, so make sure to take a good look around all of the corners, they're sneaky little bastards. Now go back and use the first aid kit if you haven't already. Now when they're all gone, use your Tommy gun, go right and sneak around the crates. Look for Sergio then hide behind a crate so that you can still see him, and he can see you enough that he'll want to keep shooting at you. When he stops to reload, get him. After he's dead, a small cut scene will play with Tommy over Sergio's body saying "You Lucky Bastard".
Some more guys are gonna show up after all this leave the harbor. You can ignore them since they don't follow you when you leave the harbor. Once you exit the harbor, either go back to the bar or go visit Lucas Bertone.
Visiting Lucas (Optional)
Lucas says that one of his friends has been shot in Chinatown. He wants you to go get him. The best route is by accessing the long-red bridge above Lucas's place and through the other bridge-tunnel. When you get there, the other guy there tells you to get the victim to the doctor's (the same doctor that you met when you had to take Sam to him). When you finally get there, the two men will thank you. Drive back to Lucas' shop after. After a small cut scene, Lucas will show you how to break in to a new car, the Bruno Speedster 851 and where to get it. When you get there, there is a guard protecting the car. Simply kill him and steal the car. When this is done. drive back to Salieri's Bar and this mission is finally done.
After the death of Sergio, the Morellos are at this point left to be dealt the death blow: the assassination of Don Morello.
- This is the longest mission in the game.
- If during the 4th attempt of killing Sergio (during the chase to the harbor) Sergio's car happens to get stuck and the player kills Sergio, the mission is failed because "Sergio Morello escaped..." even if the mission objective is "Kill Sergio Morello." meaning the harbor part is important to the plot and cannot be skipped.
- If you killed Sergio Morello with a baseball bat, he will still have a bullet hole on his forehead.
- If you lure the enemy car from the Italian Garden Restaurant to Salieri's Bar, you can unlock it.