Mr. Sinister is a sadistic crime lord operating in Sinister-port.



Note: This is set in an alternative continuity and not in the same universe as The Sinister Three or Third Street Girls.

Mr. Sinister worked as an enforcer for the Corleone crime family when he was a young man. His wife Samantha was kidnapped by a gang known as the Morningstar, who used her in their sex trafficking business. Mr. Sinister worked his way up the Corleone family and eventually broke off to run his own crew, known as the Sinister Faction. He found out Samantha was being held captive in Steelport, and traveled there and rescued her from the Morningstar. Planning revenge against the Morningstar, he moved his operations to Steelport, and went to war with the Syndicate.

When Cyrus Temple and senator Monica Hughes declared martial law on Steelport in an attempt to wipe out the 3rd Street Saints, Samantha was one of the many casualties killed in the chaos. Although Cyrus was killed by the Saints leader Bob Wilson, Mr. Sinister developed a deep hatred for the 3rd Street Saints and planned to overthrow Wilson following him declaring Steelport as an independent city state.

The Sinister Three

Mr. Sinister along with Sentient Jack, Anomin 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.

One of Mr. Sinister's most fonded goals is to have sex with the woman he has fantasized for years, that being Shaundi. He has Sentient Jack kidnap, Fun Shaundi and Viola, he becomes pleased with this and has Sentient Jack become his right-hand man, Fun Shaundi technically being the woman that Mr. Sinister had fantasized about, has uncomfortable sex with her where it then goes to rape. Things go well until Shaundi breaches into the attraction and attempts to escape with her surrogate sister, luckily he stops her and chains her up with Viola and holds Fun Shaundi hostage. He approaches Shaundi and reveals his lust for her and how for years he has been wanting to join Shaundi's sex life, however Shaundi angrily refuses to get laid with the man who had kidnapped her and chained her up. He then becomes furious hearing this and decides that the only way he can have sex with her is to threaten her, he tells her that if she doesn't get into a sexual activity with him and his comrades, he will execute Fun Shaundi, this convinces Shaundi enough to comply, having to have sex with her kidnapper against her own will, Mr. Sinister becomes pleased with this outcome and proceeds to brutally rape Shaundi having his men with him joining in. After an hour of fulfilling his goal, despite his words he executes Fun Shaundi in front of Shaundi, after so he orders his men to lock her up as a sex toy in which she is chained up alone in a dark cell where he plans to visit the room from time to time so he can fuck her all he wants.

He has Fun Shaundi's body stuffed and uses it as mannequin for display. He then turns to decide Viola's fate, at first he believed she would just be like the rest of the captives and would have her caged up, but to his surprise she openly shows how horny she is for him, in this moment, he has hardcore sex with her, such as titfucking her and penetrating her ass as well as fisting her, having enjoyed the sex that he hadn't had in a while with someone who actually wanted to be with him, he has her placed in a cozy cell and not a dark one. Moments later he gets a call coming in from his officers reporting in that there has been a break in by Kinzie Kensington, he and Sentient Jack decide to spare her and intend to recruit her. After a long chat with Kinzie they play on some of Kinzie's insecurities and make her believe the 3rd Street Saints are using her, and get her to join the Sinister Three, Kinzie feels more then grateful for having him reveal to her the "truth", they get into a relationship after a bit of talk and then have sex, choosing her over Viola.

Later, he receives a call that Shaundi has escaped and that she had killed a Sinister upon escaping, Mr. Sinister is more then angry upon hearing the news and decides to have Viola take the place of Shaundi, so he gives his men along with Sentient Jack orders to perform sexual abuse on Viola until she is completely immobile so they can then use her as the sex toy they were going to have Shaundi as instead. However, minutes later, Viola all of a sudden vanishes, this leads Mr. Sinister to believe that there is a traitor in the Sinister Three and keeps an eye out.


With his key members now defeated Mr. Sinister escapes to the helipad at the top of the Syndicate Tower in order to escape, however his transport doesn't arrive. He is soon cornered by Shaundi, Viola, Cypher and his other victims. Cypher reveals he has no where else to run and he will suffer for his heinous crimes. Refusing to be taken so easily, Mr. Sinister jumps from the top of the tower to his death, and even though his reign of terror was over he had still robbed the Third Street Girls chances of justice and to inflict their own personal revenge on him.

Mr. Sinister's corpse was taken away and secretly buried in an unknown location. Afterwards the rest of his empire crumbled and the Third Street Girls reunited with the 3rd Street Saints.

Farewell Mr. Sinister

Mr. Sinister escapes Hell to "the other world" in which he is now a kind loving businessman with a young daughter called Sam. But he misses his original life as a sexual deviant, so leaves for new parts looking for further murder victims.

Sinister and Company

Mr. Sinister spends a year of success, despite missing his old crew. One day he is abducted by an organization known as the The Company who bring Mr. Sinister to an alternative universe. He meets the Company's director Derek Robertson who reveals he is very impressed with Sinister's work, and wants him to be part of his plans for the invasion of the multiverse. Sinister agrees to the opportunity and begins working in the Company's base of operations Industrial 17. Be oversees a project known as the Prowler, a group of creatures bred as assassins. He kidnaps numerous test subjects across the city for them to be brainwashed into the Prowlers and leads his own private army.

Sinister comes in contact with his alternative universe counterpart Nathan, who he tries to convince to join his cause. Although Nathan is tempted, he later turns down Sinister's offer after feeling guilt for his inhumane actions. Sinister is angry at being turned down and abducts his daughter Sam and threatens to kill her in front of Nathan, as he is aware Nathan himself had a daughter whom he had lost a few months previously. They have a stand-off on the roof, but another version of Nathan arrives and surprise attacks Sinister. After a fight on the roof Sinister loses his footing and falls to his death.

Sex life

Mr. Sinister's role as being heavily sexually active has given him many times to immediately have sex or rape many people. He claims his favourite sex position during rape is doggy-style, but when he is casually having sex he will tend to either have missionary or standing.

He is sexually linked to:

  • Unnamed Wife: He and his wife likely had sex after marriage, in which lead to the birth of his daughter Sam. It is hinted that his wife died due to the amount of unprotected sex he had with her.
  • Sentient Jack: It is hinted heavily that at some points when he had first met Jack, they apparently engaged in sexual activities together.
  • All Sinister Three Members: According to the rules of being part of The Sinister Three, every member has sex with Mr. Sinister, meaning he has had sex with all of his members.
  • Many Sexual Captives: When forcefully bringing someone to the attraction, Mr. Sinister rapes most of his captives who refuse to join.
  • Four Female Porn Stars: As one of his main goals is to have sex with those he fantasizes, he has had sex with several porn stars.
  • Fun Shaundi: After kidnapping Fun Shaundi and Viola. He rapes Fun Shaundi as she was so far the closest thing he had to the real Shaundi as his big goal is to have sex with her.
  • Shaundi: After Shaundi gets kidnapped, Mr. Sinister forces her to have sex with him otherwise he would take Fun Shaundi's life, he brutally rapes her in the process and has his henchmen join in with him. Completing his long life goal of having sex with the woman he had highly fantasized.
  • Viola DeWynter: Viola pretends to show lust to Mr. Sinister and has hardcore sex with him in hopes that he will not give her the same treatment that he did Shaundi.
  • Kinzie Kensington: After convincing Kinzie to join The Sinister Three, he and her start their romantic relationship by having sex with each other, taking Kinzie's virginity.


Mr. Sinister presents himself as a calculating and manipulative individual, and enjoys to lure his victims into a false sense of security. He also comes across as cold and sadistic, and doesn't flinch at the thought of murder or putting someone through unnecessary stress. However in his delusional mind, Mr. Sinister believes he is doing his victims a favor, and sometimes views the world as a cold and horrible place and life a horrid existence.

Much of Mr. Sinister's life prior to The Sinister Three is uncertain, although he claims he was a decent alright person, but after a lot of disappointment, losses and downright tragedy, saw the world a horrible place. Exactly what happened is unclear.

Despite his cold feeling towards most human beings, Mr. Sinister harbours a strong respect for his close allies and those he feels are doing the right thing. However this doesn't count for mere acquaintances or associates, or the generic foot soldier, who he sees as just expendable and has little thought towards their deaths.

Overtime with his gain of power, Mr. Sinister felt nothing for anyone and even brought fear to those closest to him, especially his ally Sentient Jack. Mr. Sinister is described as a "sexual psychopath" and enjoys the humiliation he brings to his victims. Mr. Sinister is also shown to being a coward when it comes to his own defeat, as he chose to take his own life rather than being taken by Cypher and the Third Street Girls, although in his final moments of insanity was shown not to fear his own death.

Appearance and skills

Mr. Sinister is a middle aged man, with a normal physique. Although his face is never revealed due to him concealing it with a skull mask during his abductions (and some assassinations) wanting to use it as a way to scare his victims and create uneasiness and tension, his facial features are described in one of his documents. He is that of an ordinary middle aged man with greyed hair and darkened piercing eyes, although he has slight scarring around the face from other undisclosed jobs, however he sees them as a thing of beauty and proof of his "bravery" when out on a dangerous job. A slight bit of his face can be seen when he is having sex with Kinzie.

Mr. Sinister is an expert assassin and killer, which had helped him gain contracts during his stay in Stilwater and earn respect.

Weapons of Choice

Murders Committed by Mr. Sinister


  • His appearance is based off a batman villain named Black Mask.
  • He has some similarities with leader of the Luchadores Killbane. Both are men who run an rival gang against the Saints, Both are allies of the Morning Star, both wear Masks with a suit and tie, and finale both of their appearances are based off villains in Batman(With Mr.Sinister being based off Black Mask and Killbane being based off Bane.