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 in 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 wait for Paulie to tell you what to do. Now walk into the phone booth and make the call. A cutscene will play showing what happens: Tommy makes the call and asks for Sergio, but one of his random goons answers instead and says he isn't there today. Not realizing it, Paulie kills the guy, with Tommy telling him it's not him. After the cutscene 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 to plant the bomb underneath his car and wait for him to start the car and 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 a guard beside it. 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 cutscene will play showing the bomb go off, only it's Sergio's mistress who dies in the blast.
Attempt 3: Rainbow Garden Restaurant
After a cutscene, drive to the location on the map. When you get there a cutscene will play, in which Sergio is talking to a few of his men and then notices Paulie. Paulie tries firing his Tommy gun only to have it jam. After the cutscene is over, wait for Paulie to get in the car and drive back to the bar.
Attempt 4 and chase Sergio
In the cutscene, Tommy explains that after so many failed attempts, Don Salieri offered the job to other members of the family, while Tommy went along as an "insurance policy". This new crew planned to trap Sergio on the train tracks in his new car and have it run over by a train on standby. After some time, Morello arrives. The crew is in position and ready, but Sergio notices something's wrong and makes his driver get off the tracks, leaving the crew in the car to be run over. After this, follow Sergio, and when he gets to his destination, the next part of the mission will start.
Use your car as cover and kill everyone here, then take out the people in the truck that just drove up. Then, move over to the building containing someone with a Pump-action Shotgun in the window. Take him out then kill the guy who comes running. Kill the remaining guy in the building, then go outside and head over to the train. Now take out all of the guys 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, get a vehicle, and drive over to the red towers.
There are two gangsters with rifles in the towers, as well as two with Tommy guns hiding behind the crates. One way to proceed is to shoot the nearby white barrel, causing an explosion and killing all four. Then kill the guy with a rifle hiding in the building across from here. There's a first-aid kit inside that building, but you should probably save it for later unless your health is very low. Now take out any remaining enemies outside the building.
The next step is to go over to the oil tankers located by the railroad tracks. Pull the lever and walk over to the left side of the front tanker. Click the action button to remove the wheel block on the train's front wheel. This will send the tanker barreling down the tracks. Then walk over to the door that it just hit, triggering a cutscene. 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.
First take out the enemies who come to you. Now take a good look around all of the corners, as there'll probably be a few more hidden. When they're all gone, sneak around the crates and find Sergio. Hide behind a crate when he starts shooting at you, and when he stops to reload, get him. After he's dead, a small cutscene will play with Tommy standing over Sergio's body saying "You lucky bastard".
There will be some more guys outside, but you can simply ignore them and leave the harbor, as they won't follow you. Now either go back to the bar or 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 take the victim to the doctor. Drive back to Lucas' shop afterwards. After a small cutscene, Lucas will show you how to break in to a new car, the Bruno Speedster 851, and its location. 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, finally completing the mission.
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 kill 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.