Lieutenant of the Sinister Three
Mr. Sinister along with Sentient Jack and with the funding of Mr. Rollers found a crew named the Sinister Three and begin abducting the females of Stilwater and Steelport as part of their ruthless sadistic deeds.
During the STAG occupation of Magarac Island when they tried to frame the Saints by killing Shaundi and Viola, Sentient Jack killed STAG soldiers and Kia, using his appearance to fool Shaundi and Viola during the "rescue", thinking he was the Boss until it was too late and were captured.
However, after witnessing Mr. Sinister have his men rape Shaundi for the life of a kidnapped Fun Shaundi and kills her anyway in front of a chained up Shaundi and Viola, Sentient Jack becomes shocked at Mr. Sinister for his extremely sadistic actions and remembers back to what happened to a close family member and starts to have second thoughts about the Sinister Three, hinting a change in heart. After the escape of Shaundi, Viola is about to suffer the same fate as she did by getting brutally raped, however Sentient Jack saves her getting raped and helps free her from the base, which leads her to heading back to the Saints HQ and informing them about Jack's actions and how he maybe a valuable asset.
Following the events of The Sinister Three triggering Jack's repressed memories, the Sinister lieutenant defects and betrays Mr. Sinister. After assisting the saints he personally breaks them out of captivity and kills some of his former associates
After helping out the Third Street Girls, Shaundi soon confronts and knocks down Jack wanting to kill him for kidnapping her Viola and Fun Shaundi which also lead to the death of her and got Shaundi raped, Jack apologizes instantly and explains that he feels major regret for what he had done in the first place and wishes to help the saints, Shaundi heavily refuses his offer to help the saints and wants him dead along with the other Sinister's, Viola defends Jack and tells Shaundi that Viola wouldn't be alive if it weren't for Jack, however it doesn't change her mind about him. As Jack is begging for his life and promises that he wishes he never had joined Sinisters after watching what they did to Shaundi and her surrogate sister in which it reminded him of his close family members when they were raped to death and were even given motivation to have casual sex for the live of another but instead got killed off anyway. Shaundi does not feel anymore convinced and decides the fate of the Sinister lieutenant.
If Shaundi executes Jack, she will feel better and will be given more motivation to attack the Sinister's, however Viola will show distrust and disgust to Shaundi for killing the man who may have been able to help the them defeat Mr. Sinister. Back at the Saints HQ after the infiltration of the Syndicate Tower and Mr. Sinister's death, Shaundi feels remorse for killing Sentient Jack and feels as though she made the wrong decision after all and should have let him live which would've given them the chance to prevent Mr. Sinister from jumping to his death and allowing her to kill him, she is comforted by the boss who tells her not to worry about having to kill a member of the Sinister Three and it was his own fault that came to his death. Shaundi thanks the boss for trying to make her feel better and the two have sex as the game ends.
If Shaundi lets Jack live, she will feel no better and does not want Jack's assistance in defeating Mr. Sinister and has him leave the Syndicate Tower before she decides to change her mind and kill him. Before he leaves Viola apologizes for the violence, thanks him for saving her earlier and hopes to see him again. As the game ends it pans over to Jack who has had his face redesigned back to how it originally was and is texting Viola if he is clarified to come join the Saints, she replies back that Shaundi feels as though she may have changed her mind that letting Jack live was the correct choie and that perhaps he is available to come to the Saints HQ and join them at some time when Shaundi feels better.
After Mr. Sinister's death, Sentient Jack took on his mantle as Mr. Sinister II and became the new ruler of Sinister-port. During the multiverse incursion, Jack was approached by the leader of a clandestine group known as Derek Robertson, who wanted Jack to become one of the elite members of his plans to conquer the multiverse. Jack agreed, and became part of his group.
Jack continued to operate in Sinister-port, which was merged with different parts of other universes to create a new planet, which was under the control of Derek's Empire. But as the universe began to crumble, Jack seized contact with Derek's Elite and locked down both Sinister-Port and Stilwater and using Zin Soldiers to guard his country. Jack got into his own civil war with The G-Man, whose dystonian version of City 17 was situated nearby Sinister-Port, and the pair of them battled over control.
Personality and Skills
Jack is know as a polarising individual, at times showing no remorse or care for others, and easily flips off vocally, but is surprisingly restrained physically. When in combat however, the only emotion shown is that of enjoyment.
When with the other crew members, he is exceptionally well friendly, although when with his captured victims, when not having sex he's pretty much a lover man, sometimes getting a little extreme with them. During sex his sexual appetite is very well apparent, his love for good looking girls like Shaundi and Viola are well noted.
Regardless of his mentality, he knows he's an evil person but has accepted such a life of crime knowing the harsh nature of life and knows only the fittest will survive, but will not hesitate to have a little fun, during business or in his own time.
The only person to potential intimidate Jack is Mr. Sinister himself, although given his respect and dedication to the Sinister leader, it is likely him just simply knowing his place as a lieutenant and not the Boss.
After Mr. Sinister tortured and killed Shaundi's surrogate sister in from of her, Jack begins to feel deep remorse for the Saint and suffers repressed nightmares and became detached from the Sinister Three. His drive to live becomes non-existent and realises the errors of his ways and decides to do something drastic.
Jack is also an expert Armourer and Doctor; earning his PHD well before joining the Sinister Three, and teaching himself on firearms in his own free time with his gun buddies, and is quite the marksman with any gun. He's also good with explosives. It is said that Jack loves his guns second only to sex, and it is most likely be true.
In a new retconned Saints Row Universe, Mr. Sinister plans to revive the Sinister Three. Pondering about Jack's whereabouts in this new timeline, he sets out in search of his old partner along with daughter Sam.
- Sentient Jack looks like Bob Wilson because he paid Image as Designed to disguise himself so he could capture Shaundi.
- Despite have no further need of looking like Bob Wilson after Shaundi's capture, he never got his original look back. The reasons behind this is unknown.
- "Come on Shaundi, let's get the hell out of here"
- ―Sentient Jack fooling Shaundi that he's rescuing her.
- "We're nearly there."
"Where the fuck are we? That isn't one of our hideouts."
"I have a confession, I'm not your Boss, can't believe you couldn't tell by my deeper voice and red eyes. Your Boss also thought you died when we blown that statue up"
"Wha...? What are you gonna do with me?"
"Make use of that sexy body of yours you slut." (Goes to grab Shaundi)
"Wha... AH... NO, NO PLEASE! NOOOOOOO!!!"
"I'm gonna enjoy fucking your feisty ass."
- ―Sentient Jack revealing himself and capturing Shaundi
- "My god, what wrong with him, he's becoming a fucking nut. Might need to keep watch and make sure he doesn't do anything to the girls"
- ―Sentient Jack expressing concern about Mr. Sinister increasingly power hungry mentality and the safety of the girls.
- "YOU FUCKING PSYCHO, WHAT HAVE YOU DONE?!"
- ―Sentient Jack after Fun Shaundi is executed.
- "You don't have to trust me, and I fully understand you wanting to kill me Shaundi."
- ―Sentient Jack as the Third Street girls questions his motives.