Jimmy Shea

"Jack and Jill went up the hill to fetch a pail of karma. Wait, that's not right, is it? Jill's up the hill...
 * —Jimmy attempting to apply his situation to an age-old nursery rhyme"

Jimmy Shea was a thug hired by Finn Conway to retrieve his wife Jillian and the man she had intended to run off with, Jack Stanton. He appears in Sinner's Reward.

Sinner's Reward
Trailing the pair to a filling station outside of the town of Silent Hill with the O'Conner Brothers, Jimmy was barely able to escape with his life, and Jillian, when the station attendant began to open fire with a shotgun. Making it as far as the city limits of Silent Hill, Jimmy's car was set upon by a pair of wolf-like creatures. Jillian was able to escape to Silent Hill, while Jimmy was killed by the creatures.

Jack, coming upon the scene and fearing the worst, began to call out for Jillian. It was, however, Jimmy that responded instead. Telling Jack that Jill had gone to town, Jimmy begins to taunt him, singing, "Jack and Jill went up the hill, to fetch a pail of karma."

Not believing his eyes, Jack leveled his gun at the man and told him to keep away, swearing to kill him. Jimmy, knowing very well that Jack would, reiterated that Jill is waiting in Silent Hill for him, and the time would come where he'd have to pay for his past. Before allowing Jack to leave, Jimmy asks Jack to do that thing that he does so well, and makes to attack the hitman. Jack shoots and kills Jimmy.