Don Salieri has an easy job lined up for Tommy, Paulie, and Sam: steal a whole shipment of cigars. At first everyone is surprised. Finally stressed by trying to explain the job at hand, he lets Paulie tell them the deal. They want Tommy to drive to a rendezvous point, steal a truck, get to the port, and start taking the crates. Tommy points out that since Sergio's death, security has been beefed up.
After the cutscene, go see Vincenzo. He will give you a Colt 1911 and a baseball bat, while he'll give Paulie and Sam each Tommy guns. After you've collected your weapons, go see Ralph. He will show you how to steal a Lassiter V16 Fordor. Get in and drive off to the street.
Go to the rendezvous point
Follow your map to Works Quarter and park at the X on your map. Once there Sam will say this is the spot. After that a cutscene will play. Paulie says that as much as he likes working for the Don, he wants to earn some more cash, and since Sam and Tommy are his friends, he wants them in. His plan is to rob a small time bank. Tommy and Sam shoot this idea down fast. After this, you and Paulie must go get the truck.
Get the truck
Drive to the Port and wait in the parking lot for the truck to come, then follow it. Once it reaches its destination, wait again and drive ahead of it and block the road. Pull the driver out of the truck and kill him, then get the papers from him. Now remove all the crates from the truck and drive it back to the harbor.
Now drive straight ahead until you see warehouses on your left. Then back your truck up against the building that has the Scorsese boxes in it. Now get out, go into the building, and walk to the boxes. The guy will tell you to move some crates to the dispatch hall.
- Violent approach
If you are going to do this violently, it's probably best to drive in and go to the left end at full speed and hit the guy behind the Scorsese building to get his Tommy gun.
The second the foreman turns his back, follow him quietly, and when he gets to the tree to take a leak, knock him out. (This alerts guards who will start shooting at you.) After that, walk back to the building where the cases are and start putting them on the truck.
- Non-violent approach
Once they are all loaded, get back in the truck and drive slowly so it doesn't raise suspicion. The other way is to do as he told you and move the boxes laid on the streets in front of the dispatch hall into the dispatch hall where there's a wooden low-deck; after you finish moving the boxes he will come to take a look and then go back to where the Scorsese boxes are.
Now go talk to him again, and Tommy will tell him that the workers at the train need him because they're having some problems. Now he's gone and you can load the boxes onto your truck. You should be able to finish before he comes back and leave with no problem.
If the foreman returns and talks with you, he will say that nobody is supposed to be touching those crates and call for guards. Also, the guard at the entrance will ask you for your papers, and if they don't match, he'll instruct the guards to attack.
Head to Salieri's warehouse
After you exit the harbor, drive to the rendezvous point and pick up Paulie.
If you are being chased by enemies, Paulie and Sam will shoot them. In this case, you will want to approach from the northwest, allowing you to pick up the shotgun without your friends getting in the way. Only three cars of enemies approach, but are easily defeated.
Once you meet with your friends, drive to the warehouse in Hoboken. When you arrive a cutscene will play, ending the mission.
In the cutscene, Paulie and Tommy start inspecting the damage. Paulie notices one of the crates is smashed and another is a little damaged. He decides to open up one of the boxes and is stunned on what he finds. Tommy takes a look and is equally stunned. Instead of cigars, they're diamonds. Paulie wants to take some but Tommy urges him not to. In the end, he puts them back just before Sam pulls up with Don Salieri. In order to find out if the Don knows about the diamonds, Tommy asks the Don if he wants them to unload the cigars. The Don responds awkwardly, making Tommy suspicious about the Don knowing of the diamonds. Just as Paulie is entering the car, Tommy tells him he'll stop by tomorrow to talk about that other thing.
- If you decide to hijack the truck while it is unloading at its destination, you will be attacked by two enemies with Tommy guns on the walkway above.
- If you get killed during this segment, sometimes the driver will not leave the harbor after the mission restarts. Reloading the game a second time allows the drive to proceed.