Playboy X

Playboy X is the protege of drug baron and gang leader, Dwayne Forge, who was recently released from prison .

 In his absence, he has become the leader of Dwayne Forge's gang, the North Holland Hustlers. Playboy is of African-American descent, and tries to act like a major "player", so to speak. Playboy's real name, Trey Stewart, is mentioned during a mission he sends Niko Bellic on, where he describes himself as being "a good guy, who wants to help people". This is somewhat ironic due to the fact he runs a drug-dealing gang. 
  
Playboy owns both a large penthouse on Xenotime Street, and a unique yellow Patriot. This Patriot is a one-off vehicle, which cannot be found outside of missions where Playboy lets you borrow it. Playboy acts like a major player, which is somewhat understandable due to the fact that he is the head of a powerful gang. Playboy is an ally with one Elizabeta Torres, who is based in the Bohan area of Liberty City. Together, the two are the most powerful drug lords in Liberty City. 
 
Playboy aimed to leave crime behind later in life, and become a legitimate real estate agent. He says he wants to 'see his name in big, gold letters'. He also says that he wants to open schools and give money to poor children. He says he wants to do this after he becomes wealthy. However, due to his house and car, it could be assumed that he is already wealthy. Playboy also tried to work into the favour of Yusuf Amir, the billionaire Arab who you encounter during The Ballad of Gay Tony. Playboy sends Niko to end a strike at a construction site - this is Amir's site, and this is his attempt to work into Yusuf's favour.
 

Choice

Eventually, Playboy becomes paranoid that the recently-released Dwayne Forge is going to try and kill him to take back control of the Hustlers. In reality, Forge is having serious difficulty re-adjusting to life outside of prison, and can barely live his day-to-day life, much less plan a violent criminal takeover. Eventually, Playboy asks Niko to kill the innocent Dwayne, as a preemptive strike. At the same time, Dwayne, recognizing Playboy's erratic behaviour, asks Niko to kill Playboy before he acts against him, not realizing he is speaking to the very man X hired to do the deed.
 
This is the first major decision of Grand Theft Auto IV. If Niko kills Dwayne, Playboy gives Niko a large sum of money, but then regrets having Niko kill his father figure, and never speaks to Niko again. If Niko kills Playboy X, he receives Playboy's penthouse apartment as a safehouse, a variation of the outfit worn by Claude in Grand Theft Auto III, and a grateful, if saddened, Dwayne becomes Niko's friend. As a result, killing Playboy is universally considered the "better" choice in this particular decision.

Memorable quotes

• "Man, it's Christmas everyday when rollin' with this nigga!"
• "I ain't scared of nobody. All them bikers is racist as shit is all!"
• "That guy and me is gonna be tight as two cellmates on lockdown."

Mission Appearances

• Deconstruction for Beginners
• Photo Shoot
• The Holland Play...

Appearances in Other Campaigns

The Lost and Damned

•  Buyer's Market