Playboy X

"In my work people change. Money changes people. But not me...I'm still a hustler from the streets."

- Playboy X

Trey Stewart, better known as Playboy X (1983-2008, optional), is a character in Grand Theft Auto series who appears as a major character in Grand Theft Auto IV and a minor character in The Lost and Damned. He is the Boss of the North Holland Hustlers and runs a crack cocaine ring in northern Algonquin, Liberty City.

Dwayne Forge's tutelage
Trey Stewart was born in 1983 in North Holland, Liberty City. He was once very book smart as a child (in later years he would become sorely uneducated), but when he was 8 or 9 he became close to the neighborhood's biggest drug lord, Dwayne Forge, who took him in like a son and taught him how to sell drugs. When Dwayne was arrested he became leader of the North Holland Hustlers. Playboy X was previously a small-time dealer, also robbing people for some time before taking over the gang and bringing it to new heights.

Leadership of the gang
Under Playboy's leadership and rejecting Dwayne's old-fashioned views, the empire went from being exclusively about drugs to expanding into other realms of business, even legitimate. Still having the most success in drug sales, he became friends with Elizabeta Torres and monitored all drug deals in the city. After 2004, he stopped visiting Dwayne in prison, and being at a selfish point in his life, probably bought his yellow Patriot within a year or two of that date (assuming, like the real-life Hummer H2, it began production in 2003. It is unique to Playboy and can only be found with him).

Eventually he was introduced to Niko Bellic through a heroin deal and the two began a business relationship. Playboy X also makes a brief appearance in The Lost and Damned where Playboy refuses to meet Johnny Klebitz during the party.

Expanding into other businesses, Playboy even dreamed of leaving crime behind entirely to become a legitimate real estate developer and "see my name in big, gold letters!". He also explains his resolve to give money to poor young blacks and schools after he's wealthy to atone for selling drugs to children (although his penthouse and luxury car insinuate that he's already quite wealthy). He sought to win over Yusuf Amir, a billionaire developer from Dubai. Amir was under intense pressure to cooperate with the Mafia, who had shut down his construction site under the guise of a union strike in order to extort funds from him. X believed he could maneuver himself into Amir's favor by employing Niko Bellic to dispatch the mob gunmen besieging the site. Niko cleared out the site in the Playboy X mission "Deconstruction for Beginners", but Amir was unresponsive. Instead of rewarding X with shares in lucrative construction contracts, he permanently closed down the construction site in memory of those who had died. It is revealed in The Ballad of Gay Tony mission "For the Man Who Has Everything" that Amir continued construction on the soon-to-be Amir Towers.

Later, Niko was sent by X to exterminate Marlon Bridges. X also gave him a Whiz Wireless Cell to keep and so X could assist Niko in the job.

Dwayne's release from prison and The Holland Play
Eventually Dwayne Forge is released from prison and tensions rise between him and X almost immediately. Playboy ignores Forge and attempts to distance himself from his former mentor, leaving Forge feeling bitter, heartbroken and betrayed. Playboy is still the Boss of the North Holland Hustlers, as eventually Forge retakes his former base of operations, the Triangle Club, from associates of Playboy's, the Trunchez Brothers. Playboy is furious and it is clear that the bad blood between the former partners is going to come to a head.

Playboy X has a private conversation with Niko, claiming that Forge is talking behind his back and attempting to usurp leadership from him, even though he claims he offered half of the business to Forge. Though apparently very saddened by having to kill his mentor, he offers Niko $25,000 to kill Dwayne. Subsequently, Niko is also hired by Dwayne to kill Playboy X after word hits the street that there is a contract out on him.

If Niko chooses to kill Dwayne, Playboy has a change of heart, upset that his "father figure" was killed. Probably in denial, he blames Niko's cold-heartedness for the betrayal and although he pays Niko the $25,000 as agreed and wishes him the best, he cuts all ties from Niko and cannot be friends with him knowing he killed Dwayne. Later, his answering machine even claims that "you don't know what you got until it's gone."

If Niko chooses to kill Playboy, he shoots his way through Playboy's penthouse and corners him in an alleyway, easily executing him and returning control of the gang to Forge. Many players choose this path, as it coincides with Niko's moral code, is more challenging than killing Dwayne and brings much more rewards; Dwayne awards you Playboy's penthouse (which he reveals he had the deed to all along), and you gain Playboy's unique yellow Patriot and Dwayne becomes Niko's friend, which eventually offers the perk of calling in Backup, his special ability. The apartment's wardrobe even includes the GTA III outfit which was worn by Claude, which can be found in Niko's wardrobe (only in Playboy X's Apartment).

Mission appearances
 * GTA IV
 * Blow Your Cover
 * Deconstruction for Beginners (Boss)
 * Photo Shoot (Boss)
 * Ruff Rider (Mentioned)
 * Undress to Kill (Post-mission phone call)
 * The Holland Play (Boss/Can be killed by Niko Bellic)


 * The Lost and Damned
 * Buyer's Market

LCPD Database record
Surname: Stewart

First Name: Trey "Playboy X"

Age: 25

Place of Birth: North Holland, Liberty City

Affiliations: Known Associate of Dwayne Forge

Criminal Record:
 * 1999 - Possession Controlled Substance: Crack Cocaine

Notes:
 * AKA Playboy X
 * Part of Dwayne Forge's crack cocaine dealing operation.
 * Assumed control after Forge's conviction.
 * Believed to have run the business with advice from Forge in prison.
 * Reported that Stewart stopped visiting Forge at the penitentiary in 2004.
 * Now believed to be head of a cocaine distribution network in North Holland.
 * Some attempts to move into legitimate business interests.

Trivia

 * If the player chooses to kill Playboy X, his profile on the online police database does not change to list him as deceased, but the in-car computer does list him as such.
 * When Playboy is cornered at the alley he will try to shoot Niko with his Desert Eagle which will jam. He´'ll then proceed to throw it on the ground which sometimes, ironically, will clear the jam, causing the gun to fire.
 * Playboy X is a big fan of hip-hop and will respond positively if The Classics 104.1 or Beat 102.7 radio stations turn on.
 * It is possible that he gained the nickname "Playboy X", due to his penthouse being located on Xenotime Street (Playboy refers to it as "X" in Blow Your Cover).
 * On the back of Playboy X's sweater, 8-Ball's business logo can be seen. This is interesting, considering he also has Claude's clothes in his penthouse.
 * Playboy may be allied or working with Armando Torres, as the all-black Cavalcade used as a weapons cache in the mission Deconstruction for Beginners is very similar to the one Armando drives in The Ballad of Gay Tony. This similarity, along with the fact that Armando sells and stores weapons in it, could imply that Playboy contacted Armando for the car to obtain the weapons Niko uses for the mission.
 * The player can skip chasing Playboy X and just kill the guys protecting him. Aim out of the window while simultaneously aiming at Playbox X with any handgun. You will see the cutscene of Playbox X being killed by Niko and the Desert Eagle dropped by Playbox X is on the floor. It has ammo and can be acquired by the player, as seen in this video:
 * During in-game conversations, Playboy demonstrates to be very ignorant about general culture. When talking about Yusuf Amir, Playboy X believes that Dubai is in Africa. He says that Yusuf and he are brothers, and they are from the same part of the world, saying "shit, we might be cousins". Niko corrects him by saying that Dubai isn't in Africa. He later claims that Jesus Christ killed John the Baptist, something that Niko also corrects him about.
 * Like most characters in the game, Playboy will don a unique helmet when riding alongside the protagonist on a motorbike. His helmet is black with a white stripe and a dark-tinted visor.
 * Playboy X may be afraid or intimidated by Johnny Klebitz, as he tells Niko to "Not even look at him the wrong way." However, he tries to make an excuse by claiming that "them bikers are racist as shit".
 * The only way the player can get his Desert Eagle from his dead body is by killing him before he enters the alleyway and begins the execution seqeunce.
 * If you kill Dwayne, Playboy will change his voicemail.
 * On Deconstruction for Beginners, if you kill Playboy on the rooftop by grenade or RPG, his binoculars will sometimes float.
 * He looks very similar to Clarence Little.