Harry Mason's connection with Cheryl was simply she was Harry's adopted daughter and he found her along the roadsides near Silent Hill.
Cheryl Mason was one half of Alessa, so basicly Cheryl and Alessa were one.
Alessa is the daughter of Dahlia Gillespie, A member of the cult in Silent Hill.
Dahlia is connected to Dr. Michael Kaufmann because he was apart of the drug trafficking. He later helped Dahlia conceive Alessa/Cheryl. Then helped Dahlia hide Alessa after she was burnt.
Lisa gave Harry very valuable information about the area and the activities of the cults. However, Lisa could not have been saved because she was already deceased.
Harry again becomes the adoptive father of another young girl, Heather. Which infact is not her real name because Harry is try to hide her from the same cult Dahlia is associated with.
Heather was created by Cheryl at the end of Silent Hill 1 and because Cheryl is Alessa that makes Heather Alessa also.
Alessa was childhood friends with Claudia Wolf. They also attended the same class. At a young age Claudia was taught that Alessa was the mother of god and throughout her adulthood searches for Alessa.
Claudia is searching for Alessa so she hires Douglas, who is a private investigator. Douglas finds out about Harry's whereabouts and his daughter Heather, who is Alessa.
Douglas soon finds out that Claudia is up to no good and soon offers to help Heather because he feels somewhat responsible for the hurt he has caused. During this time Father Vincent (Also apart of the cult) give Douglas and Heather helpful clues and information.
Father Vincent and Claudia Wolf are apart of the same cult but both hold different values regarding their religion. Vincent admires Claudia's faith to a point but is also worried about her at the same time.
Claudia is the daughter of Leonard Wolf. Leonard himself is a very long running and respected member of the cult. He is the protector of the Seal of Metatron.
Leonard was apart of the cult at the same time as Dahlia so they were fellow worshippers.
Dahlia is the one that keeps preaching to Claudia and others about an alternate way of looking at the cult's religion. Vincent even goes as far as calling Dahlia a "crazy old hag." and also claims that Dahlia brainwashed Claudia and others.
Miscellaneous connections: Claudia is the one that exicuted the death of Harry Mason. Doing so it caused the fetus inside of Heather to be nurtured by Heather's new feeling of hate toward Claudia for killing her father. However this is what Claudia wants so that the god can be properly born.
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