Playboy X

"Well I'm always looking for good guys. Build an army. But in my work... people change. Money changes people. Not me. I'm still a hustler from these streets..."

- Playboy X to Niko Bellic in Deconstruction for Beginners. "Whassup, money?"

- Playboy's catchphrase.

Trey Stewart, better known as Playboy X, is a character in the Grand Theft Auto series who appears as a main character in Grand Theft Auto IV and a minor character in The Lost and Damned. He is the head of crack cocaine distribution 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 refrain from this positive work ethic) when he was eight or nine, he became close to the neighborhood's biggest drug lord, Dwayne Forge, who treated Stewart like a son and taught him how to sell drugs. Forge states that Playboy was always a bright kid, but he had no street knowledge so he taught him the rules of the game. When Dwayne was arrested, Stewart became the head of Dwayne's business interests. Playboy X was previously a small-time dealer, also robbing people for some time before taking over the cocaine empire and bringing it to new heights.

Leadership of the business
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 (even legitimate) business. 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.

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 property 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 manoeuvere himself into Amir's favor by employing Niko Bellic to dispatch the mob gunmen besieging the site. Niko vacated the site in Playboy X's 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 handset to keep and so that X could assist Niko in the job, as it requires Niko to send an MMS which his second-hand Badger phone given to him by his cousin Roman is incapable of doing as it does not have a camera.

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 streets 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. Presumably 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 with 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 by shooting him in the throat, and thus, returning control of the North Holland Hustlers gang to Forge. As a token of his appreciation, Dwayne gives Playboy's penthouse (which he reveals he had the deed to all along) to Niko.

Personality
Playboy presents himself as an altruist who one day seeks to help the poor in his community. However, his actions and even his words prove that he is a materialistic hypocrite, as he states in his introductory mission: "If a deal make paper, I do it." His missions consist solely of him chasing more wealth to seemingly do nothing with, while he touts that he is still the same young hustler from his youth, unchanged by money. Despite this, he heavily values connections and treats his peers as tools and means to an end rather than valued friends, as he treats Elizabeta as a mere business partner with a great deal of hookups, ignores Dwayne after the latter's imprisonment and resulting loss of usefulness to him, and discards Niko as a partner should the player kill Dwayne instead of him. Ironically, this last example is the only time when Playboy seems to value someone (or more accurately, their memory) for more than business connections.

In his youth, Playboy was quite booksmart, although by the events of GTA IV, this has clearly changed, as he claims Jesus Christ killed John the Baptist and that he and Yusuf Amir might be cousins simply because he believes Dubai is in Africa, which Niko quickly refutes on both occasions only for Playboy to ignore him. He also appears rather cowardly, as he prefers to simply hear and oversee drug deals and other dangerous situations as opposed to actually taking part in them. This can be seen in all of the missions he appears in, as he hides and blindfires in the only mission he is in a firefight, and has Niko do his dirty work in the other ones. If the player chooses to kill him, his cowardice can be seen even more prominently, as he quickly abandons his fellow gang members and even drops his weapon once cornered.

Mission Appearances

 * GTA IV
 * Blow Your Cover
 * Deconstruction for Beginners (Boss)
 * Photo Shoot (Boss)
 * Undress to Kill (Post-mission phone call)
 * The Holland Play (Boss/Can be killed)
 * The Lost and Damned
 * Buyer's Market

Trivia

 * Playboy X bares a vague resemblance to the American rapper.
 * 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.
 * Playboy X's favorite radio stations are The Classics 104.1 and Beat 102.7.
 * On the back of Playboy X's sweatshirt, 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 (when he said to Niko that he would be "One sec" in the mission cutscene) for the car to obtain the weapons Niko uses for the mission.
 * Like most characters in the game, Playboy will don a unique helmet when riding alongside the protagonist on a motorcycle. 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."
 * During Deconstruction for Beginners, if the player kills Playboy on the rooftop with a grenade or RPG, his binoculars will sometimes float.
 * He shares a similarity with "The Wire" character Stringer Bell in that he wants to expand into legitimate business while Dwayne shares a similarity with "The Wire" character Avon Barksdale in that he accepts that he is a criminal and wants to continue to conduct business as he has in the past.

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