Heywood is a member of Red's gang who are long sentence serving convicts. He is first seen taking bets on who would will crack the first night. Heywood bets Fat ass and wins this bet and gets a pack of cigarettes.
Heywood takes another big part in 1954 where one of their friends crack, Brooks Hatlen. As Floyd tells Andy and Red this, they come rushing over to see what the problem is. There, they see Brooks holding a knife to Heywood's throat. The reason why Brooks was doing this was because he was going to be released from prison and killing Heywood would of the been the only way for Brooks to stay. Andy and Red talk Brooks down and Brooks eventually accepts his fate.
A short while later, Brooks has sent the gang a letter saying he killed himself. Heywood thought that Brooks was crazy for holding a knife to his throat and went on about how insane he went, however Red tells him to knock it off. Red then says that after being in prison so long, Red thought he was insitutionalized.
Despite not liking Andy at first, he becomes good friends with him as time goes on. Heywood can be seen to have great respect for Andy when Andy escapes from Shawshank prison in 1966. Over the next year, him, Red, and Floyd have conversations and laugh about Andy's story.
