X began his criminal career as a crack dealer in Liberty City, working for Dwayne Forge. Forge ran the Hustlers at the time, controlling the majority of crack cocaine in northern Algonquin and Bohan. When Forge went to prison in 1993, X took over the gang (at the age of 10), and brought it to new heights.
Playboy became one of the premier gangsters in the city, and his success earned him a lavish penthouse in North Holland. Almost immediately Playboy began to turn away from the "old school" values taught to him by Forge and began the 21st century as a 'gangsta', favouring bling and increased reputation over loyalty. He also sought to expand his horizons, becoming friends with cocaine empress Elizabeta Torres and monitoring all drug deals in the city. Eventually he was introduced to Niko Bellic through a heroin deal and the two began a business relationship.
The major move between the two involved pressuring Yusuf Amir, an entrepreneur from Dubai in the United Arab Emirates. 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 favour 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.
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. Eventually Forge retakes his former base of operations, the Triangle Strip 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 drives a unique yellow Patriot that cannot be found anywhere else in the game.
He is voiced by Postell Pringle.
The Holland Play
- Main article: The Holland Play (Mission)
In a mission entitled "The Holland Play", Playboy X offers Niko $25,000 to kill Dwayne Forge. He alleges that Forge is talking behind his back and attempting to usurp leadership from him, even though PBX claims he offered half of the business to Forge. Subsequently, Niko is also hired by Dwayne to kill PBX 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 mentor was killed. He blames Niko's cold-heartedness for the betrayal and severs all ties from Bellic, threatening him for his actions. Later, his answering machine even claims that "you don't know what you got until it's gone." If Niko sides with Forge, he shoots his way through PBX's penthouse and corners him in an alleyway, easily executing him and returning control of the gang to Forge.
If the player chooses to perform an execution with a pistol on Playboy, Niko plants the barrel of the gun directly underneath Playboy's jaw, and shoots him point blank, making an exit wound through the top of his head.
As a token of gratitude, Forge gives Niko the apartment Playboy once inhabited, along with the GTA III outfit which was worn by Claude, which can be found in Niko's wardrobe (only in Playboy X's Apartment).
Playboy X claimed that his goal in life was to make enough money to support young African-American youth in Liberty City. He hoped to become a major philanthropist and community hero.
- After killing Playboy X, his profile on the police database does not change to list him as deceased.