Reginald Thomas "Reggie" Winter, commonly dubbed Reggie the Reckless or Reckless Reggie by others, was the younger brother of Demon and the grandson of George, the cook at the Pinehurst Youth Development Center, who was the deuteragonist of Friday the 13th: A New Beginning. Reggie daily hangs around there and seems to know every resident at the house, especially supervisor Pam Roberts.


One day, he surprises new arrival Tommy Jarvis by hanging a large rubber spider in front of him. Tommy retaliates by donning a latex monster mask, a talent he has for mask-making. Reggie picks up the monster mask to get a closer look at it, but Tommy grouchily snatches it from him and tell hims not to touch. Reggie says he acts as though he built the mask himself and Tommy confirms he did, to which Reggie amazingly says "Solid". After some small talk, Reggie leaves Tommy to check out the sounds of police sirens, but he was held back by George and misses out on the action.


Reggie scares Tommy Jarvis with a rubber spider.

Reggie was also not around when resident Joey was brutally killed by fellow resident Victor J. Faden. The next day, Reggie asks George if he can go see his brother Demon, who was in town, and George says maybe. When everyone but resident Eddie shows up for breakfast, Tommy is sent to go get him. Before he can leave, Eddie shows up wearing one of his masks and startles him. Everyone laughs at this but it isn't so funny when Tommy grabs Eddie and flips him onto a nearby table and then begins to beat him up.

That night, Reggie, Pam, and Tommy go to visit Demon at the trailer park where he's staying. Reggie catches up with Demon and is introduced to his girlfriend, Anita. Unbeknownst to them while they are catching up, Tommy is fighting Junior Hubbard, the mentally retarded son of the mean local, Ethel Hubbard. When Tommy runs off after realizing what he's done, Reggie and Pam leave Demon and Anita and heads back to the house.

Arriving there, Reggie discovers from the remaining residents Jake, Violet and Robin that George and fellow employee Dr. Matthew Letter had been gone for hours searching Eddie and his girlfriend Tina, who themselves were missing earlier. Reggie is sent to bed while Pam goes to searches for Matt, George and probably Tommy.

Shorts hours later, Reggie wakes up and wonders around the house to see if anybody was there. He goes to Tommy's room to see if he's there but instead he finds the murdered bodies of the remaining residents. Backing out fearfully, he bumps into the newly returned Pam and she see the bodies as well.

When he and Pam flee downstairs, the murderer Roy Burns (Joey's father who was irrationally trying to avenge his son's death) comes bursting in wearing a Hockey Mask with two blue markings and a bloody machete, mirroring the infamous Crystal Lake killer, Jason Voorhees; him being responsible for the deaths of the remaining residents and everyone who went missing had also been killed by him. Roy chased Reggie and Pam and Reggie ran off more faster than she did. He shortly reappeared on the tractor Victor was on when Tommy was being brought in Pinehurst and rammed it into Roy's stomach when he was to about kill Pam.

They ran into the barn and Pam faced Roy with a chainsaw before Tommy arrived and backed them up. The fight lead to the upper loft where Reggie knocked him out the window but somehow he managed to hold onto the ledge and grab Reggie's leg, trying to pull him down. Tommy got Roy's machete hit him with it sending him falling onto tractor harrows where he died and his hockey mask was knocked off. Reggie was last seen sleeping in Pam's lap. Reggie was presumably sent to a mental institution or foster care since he had no other family.

In the original script of Jason Lives, Reggie was revealed to have been placed in a mental institution alongside Tommy, and was killed by Jason when he rose from the grave. However, despite the film was being a direct sequel to New Beginning, he and Pam were rewritten out of the film. 

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