|The Holland Play|
Playboy X and Niko talking about Dwayne.
|For||Playboy X and Dwayne Forge.|
|Target||Playboy X or Dwayne Forge|
|Location||North Holland, Algonquin|
|Fail||Dwayne escapes, Playboy escapes|
|Reward||$25,000 or Claude's outfit, Playboy X's apartment as a safehouse, and Dwayne as a friend.|
|Unlocked by||Photo Shoot, Undress to Kill|
After completing both missions for both Dwayne and Playboy, Niko will receive a phone call from Playboy telling him to meet him at his apartment. Niko goes there and Playboy talks with him about Dwayne. He tells Niko he has tried everything he could to reason with Dwayne. Niko jokingly says to kill Dwayne and Playboy believes this is the only option left. Niko then expresses his distaste for conversion to which Playboy agrees. He tells Niko he will pay him after which Niko leaves the apartment to think.
After conversing with Playboy, Niko leaves the apartment and receives a phone call from Dwayne. He had heard that Playboy intended to have him killed. At first, Dwayne considered allowing himself to be killed, but felt he wasn't ready. He then asks Niko to kill Playboy for him because he couldn't do it himself as he used to be close to him when they were both younger. After talking with Dwayne, Niko is given the choice to kill either Playboy or Dwayne.
If the player chooses to kill Dwayne, Niko will enter Dwayne's apartment and question his presence there. Niko responds by saying it isn't personal. He enters the apartment and disposes of a homeless man with a baseball bat. He finds Dwayne and prepares to kill him. Dwayne calls Niko a snake and Niko puts a pistol to Dwayne's head, turns away and shoots him in the back of the head. After this, Niko calls Playboy to tell him Dwayne is dead. Playboy pays Niko as promised but berates him for killing his former mentor. He then proceeds to cut all contact with Niko, calling him a "cold hearted killer" and telling him he hopes he can find something to live for.
If the player chooses to kill Playboy, Niko will confront Playboy and other gangsters in his apartment. Playboy questions him, believing Dwayne was easily killed. Niko denies this and much to Playboy's surprise, reveals his intentions to kill him. Playboy flees and leaves the gangsters to kill Niko, although they fail. Niko then chases Playboy down a building and finally into an alleyway. Playboy tries to open a door which was locked. When Niko enters the alleyway, Playboy attempts to shoot his Desert Eagle but it gets jammed, leading him to throw it on the ground and surrender himself. Niko corners him and Playboy calls him cold and exclaims "he was someone" and he "changed the game". Niko aims a pistol at Playboy and tells him the game changed him before then shooting Playboy through the throat. Afterwards he calls Dwayne to tell him Playboy is dead. Dwayne tells Niko he should have watched Playboy closer when he was younger and feels astounded that his former friend could have betrayed him. He then tells Niko he has the deed to Playboy's penthouse and gives it to Niko telling him he can't keep it because it would make him remember Playboy. He also asks that Niko visit him sometime since he doesn't have any friends left.
- Choosing to kill Dwayne will reward the player with $25,000.
- Choosing to Kill Playboy will reward the player Playboy's apartment to use as a safehouse. Along with this the player will also unlock an outfit bearing resemblance to the clothes worn by Claude, the protagonist of Grand Theft Auto III. Dwayne can also become a friend if the player responds positively to an email sent from Dwayne.
- By killing Playboy while he is on the roof of the penthouse, the player can obtain his Desert Eagle pistol.
- Humorously, when Niko corners Playboy in the alleyway, Playboy will throw his jammed Desert Eagle on the ground. Upon doing this, the pistol can actually fire a shot which can injure the player.