In the year 2006, a young playa walking the street of Stillwater getting stuck into the middle of a gang war attempt to gun him down; however, the 3rd Street Saints, led by Julius Little, step in and save him.

With the lack of female companions, the Playa sets out to help Vikki's business by bring her girls back.

Needing to keep the press away from a bunch of clients for some private activities, the Playa helps them out.

The Playa meets Johnny Gat and Dex at the church. Gat briefly scrutinizes the Playa before introducing them to the Vice Kings and their leader Benjamin King. Playa meet with Johnny and Aisha, needing his help to get Aisha out of her record label as they are extorting her. Gat fills the Playa in on Tanya Winters, needing the Playa to go get her at Prawn Court and securely damage the Vice Kings' operations.

Johnny calls the Playa up to warn them to stay off the streets, as the PD are pressing down on the Saints. However, after learning that the Vice Kings are using this time to get Tanya's brothel, back from the Saints. At the church, Playa and Gat prepare for an assault on the Abandoned Police Station which is being used as hideout for Tanya.

The Playa meets Julius, Dex and Aisha at the church. Julius asks the Playa to pose as Tanya's chauffeur to find out where Gat is being held. Dex has a plan to force the police to put pressure on the Vice Kings, which involves Gat and the Playa dressing as Vice Kings gang members and running riot in Stillwater.

Dex has discovered that the reason the SPD have been going so easy on the Vice Kins is because they've been getting in on some their protection rackets. Dex plans to go public with it, but Gat arrives with multiple RPG taken from Anthony's Condo. Warren and Tanya have overthrown King. After a failed assassination attempt, he escapes with an injured arm and calls his old friend Julius for help.

At the church, Julius holds a meeting with Benjamin King, the Playa, and Gat, and give King an ultimatum: "Keep his pride and die or be a man and walk away." King chooses neither, and instead opts to kill Tanya first. Julius agrees and sends the Playa with King downtown. At the church, Gat explains to the Playa that, according to King, Tanya's Takeover of the Vice Kings didn't go as smoothly as planned; the Vice Kings are fighting amongst themselves, and Gat believes now is the perfect time to finish them off.

Need the money from her ex-husband, Mary task the Playa to cause damage in down.

Marvin is a drug dealer who believes he has the best product in Stilwater and understands that stealing junkies away from other gangs got them quite angry. So, he hires the Playa to ride shotgun on his deals as protection.

Sam needs the Playa to steal some cars for his new start-up business.

In a meeting with Dex at the church. He briefs the Playa on the Carnales, the powerful gang which dominates Stilwaters's drug trade." "Dex and Troy meet with Playa outside Freckle Bitch's to discuss a plan on attacking the Carnales' main drug plant."

"Dex is about to reveal his plan on attacking Los Carnales' main drug plant to Playa at the church when a 3rd Street Saints gang member reveals the Carnales have launched an attack on the 3rd Street Saints, led by Angelo Lopez and Victor Rodriguez." "Troy and Dex, outside Samson's garage, discuss the plan of attack on the Carnales' main drug plant."

"Troy and Dex meet Playa at a Friendly Fire. Dex has bought a McManus sniper rifle for Playa, and wants them to use it to kill Hector Lopez, leader of the Carnales, during a meeting with the Colombians, to disrupt their drug dealings and make the Carnales believe the Colombians killed Hector."

"Dex and Troy meet Playa once again at the church to discuss their plan of action. With Hector Lopez now dead, the Carnales are feeling the hurt. Troy recommends they kill Manuel Orejuela next, as he's "the mouth piece for the Colombians", thus crippling the Carnales for good." "Back at the church, Julius Little sharply criticizes Dex over his decision to meet the Colombians without consulting Julius first, while Troy and Playa listen. Still furious over Hector Lopez' death, and how Dex and Playa escaped him, Victor Rodriguez storms the church with fellow Carnales."

"Dex meets with Troy and Playa at the church and informs them that if they can get the drugs back that the Stilwater Police Department seized, then Manuel Orejuela and the Colombians will stop dealing with Los Carnales and deal with the 3rd Street Saints instead." "Dex meets Playa outside the church and decides it is time to take the fight to Angelo Lopez at the Lopez Mansion, using the address given to them by Manuel Orejuela." "Dex pulls up alongside Playa outside the church and informs him that Angelo Lopez and the remaining Carnales are trying to flee Stilwater."

A businessman name Ralph need the Playas help with a list of shipments from our competitors that he needs robbed.

Lin meets Playa in secrecy outside the Ultor Dome in the Arena District. She explains that she hasn't found too much information on the gang, aside from a delivery of high-performance vehicles arriving today. She asks Playa to steal the Peterliner carrying the vehicles and deliver them to Samson, who loads them up with "a few surprises" before finishing the delivery. Lin meets Playa in secrecy yet again, this time dancing in a nightclub, and congratulates them on a job well-done regarding their work. She says that after Playa delivered the vehicles to Samson, he loaded them up with explosives, before delivering them to the Westside Rollerz, who were none the wiser. Lin meets Playa undercover yet again, this time in a bar. She is not happy with how her work is going and has devised a plan to get in deep with the Westside Rollerz: she wants Playa to find a mechanic called Donnie, who is a personal friend of Joseph Price, who runs the gang. Lin, while still undercover as a Westside Rollerz gang member, drives up and save Donnie from Playa, making it look like Lin saved his life from the 3rd Street Saints, and hopefully a grateful Donnie leads Lin to Joseph Price.

A grateful Donnie takes Lin to meet Joseph Price and William Sharp at Price's Mansion, while Playa eavesdrops from outside the window. After a short conversation, Donnie lets slip of a raid on a convoy the Westside Rollerz are planning later that day. William Sharp and Joseph Price discuss Donnie's value to the Westside Rollerz; Sharp accuses Donnie of being a "nimrod", while Price defends his best friend, stating he always "steps up at the end". Donnie and Lin then enter the room, revealing they have a plan to get the parts for the buyers after their previous plan failed: simply strip four key cars that already have the particular parts.

Angry at what the 3rd Street Saints have done to the Westside Rollerz over the course of the Westside Rollerz story arc, and over the death of his uncle, William Sharp, and the disappearance of his best friend, Donnie, Joseph Price rallies his gang to burn the 3rd Street Saints' home turf, Saint's Row District, to the ground. Joseph Price attempts to run over Playa in a Goliath truck at Foreign Power, where the two were supposed to meet and have a showdown that Price had challenged Playa to in a phone call.

With Stilwater under control of the 3rd Street Saints, it would seem like their troubles are over, but not long after Playa is promoted to second-in-command of the gang by Julius Little, Chief Monroe calls them up outside the church. While Johnny Gat, Dex, and Playa discuss Julius' fate over at the church, they receive a phone call from Chief Monroe, who has decided to renege on letting Julius go until the 3rd Street Saints do more "community service" for him. Dex quickly formulates a plan and decides to assassinate Monroe at Marshall Winslow's funeral. Playa receives a phone call from Alderman Richard Hughes, with Marshall Winslow and Chief Monroe dead, Hughes would like to meet Playa aboard his yacht; he believes they can have a healthy relationship, and even promises that Julius Little will be there.