Jacob is waiting for you in a car in Alderney. Get to him and get inside. Jacob points to a mysterious car nearby (Huntley Sport); they're Jimmy Pegorino's men. Make a T-Turn to begin the pursuit (go in reverse with the stick full right; wait for front end to swing around; throw into forward with stick full left; brake when the car has turned back to the opposite direction you started in). There will be an immediate tight right turn onto the Plumbers Skyway you must negotiate. The car you are driving is fast, but steers and brakes poorly. Chase after Pegorino's goons. They will mainly follow the highway, and swerve in and out of both lanes. Watch out for other cars heading the other direction. Do not waste time firing on the car, concentrate on making it safely to the finish of the chase. After a few minutes, the chase will end in Northern Alderney on the beach near Leftwood. Be especially careful not to roll the car, which is easy to do in a couple of the tight turns the chase will take.
The target vehicle drives to an abandoned casino, Dimitri and Pegorino's hideout. A cutscene shows Niko's car sliding to the side and stopping. Niko and Jacob get out, take out their weapons and gain cover behind the car. Niko tells Jacob to go home and stay there until Niko really needs his help. Jacob runs away as fast as he can and leave Niko to clean up Dimitri and Pegorino.
Dimitri is in the old casino. Before you can find him, you will have to shoot all of his guards outside the casino, then inside the casino. This is a standard shootout although the enemies do have some heavy weaponry. Don't worry about chasing Dimitri yet, just get rid of his men. Eventually, a cutscene will play as you follow Dimitri's tracks; Dimitri betrays Pegorino and executes him. Dimitri escapes to the roof and runs to a helipad. Niko must shoot more of Dimitri's men and chase him. Dimitri then get's into a helicopter and prepares to leave. Niko quickly grabs hold of the helicopters skids but one of Dimitri's men stomps on Niko's hands, sending him falling into the water next to a nearby boat.
Board the boat quickly and move away from the casino as fast as possible. You will hear, but not see, a rocket fired from Dimitri's helicopter at your boat. If you do not smoothly board the boat and begin moving, you will be killed, or the boat will be hit; both will fail the mission. Take control of the boat and carefully chase Rascalov's helicopter down the West River until you see Jacob's Annihilator fly into the scene. Chase Jacob's helicopter and get under it to climb on.
Work your way onto the helicopter and take the steering. If you haven't flown an Annihilator before, be advised that the controls are much more sensitive than the Mavericks owned by Brucie and Helitours- use small movements. Fly after Dimitri's helicopter but don't use the mounted miniguns like the game prompts. This is just wasting time since Dimitri's helicopter has infinite health and it's also a bad idea because you'll risk getting hit by the rocket launcher's missile. Just as in the road chase in Alderney, focus on completing the air pursuit safely. You can do this by immediately gaining as much altitude as possible. If you hit even one of Algonquin's tall buildings then you will almost definitely fail.
One of Dimitri's men fires a Rocket Launcher at Niko. Jacob responds with shots from his carbine. Eventually, Jacob damages Dimitri's helicopter and sets it ablaze, after Niko's copter is hit with a Missile. Both choppers crash on Happiness Island with Niko, Jacob, and Dimitri's goons narrowly surviving.
Find Dimitri and empty every bullet you have into him, for Niko, and for Roman, and he will go down in no time with powerful weapons such as the Carbine Rifle or Assault Rifle. Watch for his henchmen and the police. Once he is down, a cutscene will play showing Dimitri dying of his wounds. Niko angrily reminds Dimitri of his traitorous nature, how he killed his best friend, on how he betrayed everyone who had ever came into contact for himself and that he killed his cousin. He then guesses that "the survival of the fittest thing" really meant a lot to him. Dimitri then dies of his wounds. Jacob arrives just in time to see Dimitri's death and tells Niko it's time to go. Niko sadly explains that Roman never hurt anyone, while Jacob understands Niko's sadness and explains that it's over and he won. Then they both walk away leaving Dimitri's dead body at the foot of the Statue of Happiness.
- After Niko falls from the helicopter, swim under the dock first, as the rocket Dimitri's henchmen fires may kill you, usually with one shot. Once the rocket has been fired, proceed to the boat and continue with the mission.
- If you are finding it difficult to reach Jacob's chopper during the boat chase then follow these instructions. Get in the boat as quickly as you can (perhaps even ignoring the first tip completely) and once you do go full throttle all the way. If you slow down for even a second you may fail the mission. Also, avoid making sharp turns as this slows down your speed.
- Do not move the joystick forward (LShift for PC) as it does not increase your speed. Once Jacob appears, align your boat exactly to the markers to ensure the cutscene triggers.
- Dimitri runs toward the Statue of Happiness. Do not follow him straight; the combined forces of Dimitri's henchmen and the police won't get you far. Instead, go around the island.
- Shooting in the island will trigger a 3-star wanted level (most likely if you kill a police officer). Be cautious.
- When you reach the roof of the casino, don't go straight out the door, as there is one henchman waiting ahead of you, and two others closing in from your right. Also, take out the goons which are on your right side first, as they will quickly come running towards you and kill Niko, causing the mission to be failed.
- If you want to refill your health on Happiness Island, you should prefer getting a hotdog from vendors which are on the side of the Island, rather than the ones in the middle.
- On the roof of the casino, Dimitri calls Niko a "Baltic swine" (свинья балтийская) in Russian. This is a mistake in the game, as Niko is from the Balkans, and indeed the English subtitles read "Balkan swine" instead.
- Jacob is waiting for you in a car in Alderney.
- Follow Pegorino's goons they'll lead you to Pegorino.
- Dimitri is inside the old casino. Find him.
- Chase Dimitri.
- Get in the boat.
- Chase Dimitri.
- Get underneath Little Jacob's chopper.
- Get low and stay close to Dimitri.
- Chase Dimitri.
- Kill Dimitri.
- Jimmy Pegorino - Killed by Dimitri Rascalov in betrayal, saying that he "didn't work this hard to share the spoils of a victory".
- Dimitri Rascalov - Succumbed to gunshot wounds caused by Niko Bellic for causing the death of Roman Bellic, attempted to kill him at Roman and Mallorie's wedding by sending in an assassin to kill him, and for betraying him twice.
- Unlocks the Annihilator
- "You Won" Trophy (PS3)
- "60 You Won" Achievement (Xbox 360 / PC)
- "Liberty City Minute" Achievement/Trophy (if the game is finished in less than 30 hours)
After the Mission
- Niko receives a call from Mallorie, informing him that she is pregnant and that it will be hard raising a son without a father.
- Niko receives a call from a sad Brucie, stressing how "wrong" the loss was.
- Niko receives a call from Kate, stating that she is there for Niko if he needs her.
- Following the credits, Niko says "So this is what the dream feels like, this is the victory we longed for."
Weazel News (Radio)
"A body has been found on Happiness Island; Police were confused when they arrived here and found two crashed helicopters and a dead russian gangster. The body has been identified as that of Dimitri Rascalov, a businessman based in Hove Beach. Police have long believed him to be at the forefront of the new wave of immigrant led organized crime."
- During the first half of this mission, the weather is sunlight, but after Dimitri kills Pegorino, it changes to rain. Also, in the beta, the mission originally took place in the sunlight.
- The remaining parts of the mission may have been set in the rain to create a dark and sad theme, as Roman, Niko's cousin and the only thing he had when he first arrived in the city, has been killed, and Niko must avenge his death.
- Jacob is still wearing the clothes he wore for the wedding.
- The Huntley Sport that Pegorino's goons are in can be blown up with Packie's bomb, after the player calls it. The bomb will go off after a certain amount of time and this will fail the mission.
- Dwayne's backup cannot be called to help with the shootout at the casino.
- Niko cannot date Kate after she calls and says she will be there for Niko, but Niko replies that he will need some time.
- Jacob, Dimitri, and Niko all mention Mikhail Faustin. Jacob mentions Niko killing Faustin during the car chase. Dimitri shouts "If only I'd let Faustin kill you!" and Niko reminds Dimitri (as he's dying) that he killed his best friend.
- This is one of only two missions in GTA IV, (the other being Out of Commission) that has a checkpoint where you can start from if you fail the mission, which is when you are hiding behind your car.
- The last missile fired by Dimitri's henchmen is scripted to hit the Annihilator.
- Dimitri's Maverick will always catch fire, even if the player deals little damage to it.
- The Annihilator is special in which it has a missing tail blade. This also occurs in Out of Commission.
- Niko will sometimes die after falling from the helicopter into the water.
- After getting into the boat, an RPG will sometimes hit Niko.
- When Niko is trying to board Jacob's Annihliator, it will sometimes hit a wave causing the arrow prompt to disappear, and resulting in mission failure (no longer a way to board the helicopter).
- Niko's Squalo will always blow up once he jumps onto the Annihilator.