Jillian Conway

"You don't need to think... Just see. See what's around you. It's all here, for you and me to finally see."

Jillian "Jill" Conway is a character from Sinner's Reward. She was married to mobster Finn Conway, but fell in love with Jack Stanton.

Background
Barely making it in the world on her own until she met and married Finn Conway, things had since become easier for Jillian Conway. Until, that is, Finn begins employing Jack Stanton. Jillian and Jack fall for each other, and soon begin sneaking around behind Finn's back. Jack, intent on marrying Jillian himself, suggests that the pair run off. Jillian is taken aback at first, stating that Finn would never let such a thing go unpunished and there was the fact that she was quite comfortable being with Finn. Jill tells Jack she doesn't want to be poor again, and running away with him would lose her a good deal of money.

Jack is unconcerned, because he knows how Finn works and who he will likely send after the pair. He also reveals he's been doing work for Finn long enough to have a substantial amount of money stashed away. He tells Jillian she won't need to worry about a thing. Reassured, she agrees to run off with Jack. With one more job under his belt for Conway, Jack completes the hit, collects the reward, and the pair take off.

Sinner's Reward
A little over a day's drive outside of Boston, Massachusetts, Jack and Jillian stop at a gas station for fuel and a bathroom break, when they are ambushed by three of Finn Conway's hired hands: The O'Conners and Jimmy Shea. With the attendant's help, the O'Conners are dispatched rather easily. Jimmy Shea, however, is able to kidnap Jillian and make a break for Silent Hill. The thug never makes it to town, however.

Just outside of Silent Hill, the car Jimmy is driving is attacked by a pair of wolf-like creatures. Escaping, Jillian heads into the town of Silent Hill on foot, while Jimmy is mauled by the creatures.

Ending up at Pete's Bowl-O-Rama, Jillian isn't seen again until Jack, having recovered from the ambush at Charon's, comes searching for her. How she came to be in the bowling alley or what she is doing there is unknown. When Jack finds her dress nailed to the outside of the building and a blood trail leading inside, he is prepared to storm the establishment. Before he can, though, a hulking monster comes bursting through the wall at him. Witnessing Jack kill what she perceives to be an innocent person, Jill becomes hysterical and starts screaming that they are in a reality they have created for themselves and all of their victims are waiting...and wanting.

Confused, Jack begins to assure Jillian that she has done nothing, so she has no victims. Seeming to reach an understanding, Jillian tells Jack he's right, that she has done nothing wrong. It is her duty, now, to do something. She then runs off.

Jillian runs to Brookhaven Hospital to try and make amends for her past, but finds she can do nothing to change what she has done. When Jack, with a girl named Sara Linwood, meets with her once again, Jill is standing over a corpse, sobbing and screaming that she couldn't save him. Jack tells Jill to calm down and says to her that they can fix the situation. She becomes hysterical once more, saying only one thing can fix what's wrong. Sara, watching from the door of the room the pair are in, suggests they leave because something doesn't feel right. All of the people in the room with them are dead. Having seen only monsters, Jack becomes confused and yells that they're surrounded by monsters. Jill retorts, saying Sara understands because she can see things for how they really are.

Jack becomes irate and tells Jill to stop with her nonsense so he can think. However, Jill says he doesn't need to think, just see. The truth of their whole ordeal is surrounding them. Sara, standing over a gurney with two sheet-covered bodies, pulls the sheet back and reveals her parents; Jack's last hit for Finn Conway. Before Jack could leave the Linwood house, Sara had seen him and Jack had killed her, wanting to leave no witnesses. As the truth dawns on all of them, a siren begins to wail, and Jack and Jill pass out.

When they regain consciousness, Jill has consigned herself to her fate, saying it's over for them. Sara, aware of the truth as well, stands before the pair with a horde of nurses. Sara offers them a chance to redeem themselves. Jack becomes angered and says Jill has done nothing. Sara agrees, saying Jill has done nothing, except drawing comfort from the riches that came with the murderers and thieves she kept company with and ignoring the dark reality of her life, too enthralled with the good fortune it brought her. Jill accepts that she has wronged in her life and says goodbye to Jack. She walks into the group of nurses, and is stabbed to death.