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|“|| Death to all who turn their backs on God!
Leonard raised Claudia as a strong believer in the cult's faith, and inflicted physical punishment and emotional abuse, such as screaming, hitting and kicking her on the floor, upon her for any irreligious behavior he caught her doing. This, in turn, resulted in Claudia bearing a strong hatred for her father. Vincent Smith also apparently witnessed Claudia being abused, claiming Leonard's cruelty is "forever burned into his mind".
At some point in time, he was condemned to Brookhaven Hospital for his insane and abusive behavior and stripped of his rank, having stabbed someone over a religious dispute, as revealed in a note. However, in his heart, he still held the teachings of the Order close with fanatical devotion. Unlike his daughter, his vision of Paradise is more exclusive, undeserving of God's non-believers.
A memo can be found of a doctor noting the Leonard's behavior; the doctor claims Leonard is usually an "ideal patient", being cooperative and having a strong sense of justice, but can turn violent when overexcited/upset, particularly when staff feel oppressed by his frequent attempts to force his religion onto them. It's possible that he was the murderer of the corpse tattoo man, evidence being found not only in Leonard's mentioned volatility, but also in a memo found beside the tattooed man. It tells that the man was found stabbed in the neck, holding a kitchen knife in his hand. Doctors assumed it could have been a suicide, but admitted that the angle was extremely suspicious. This could point to Leonard being his assailant.
Silent Hill 3
Heather Mason searches for him in Brookhaven Hospital to acquire an artifact she and Vincent believe can prevent the birth of God: the Seal of Metatron. In Room S12 on the third floor, Leonard calls a phone in the hospital for reasons primarily unknown, although from the call it can be assumed he was trying to reach Claudia. Heather answers and not knowing of his connection to the Order, she and Leonard find a mutual dislike of Claudia, whom he thinks is a fool. Simultaneously however, Leonard reveals to surprisingly have a minute sense of care for his daughter, considering his voice mollifies slightly and indirectly disproves of Heather's words when she voices she yearns to kill Claudia since Claudia killed Heather's father. Towards the end of the phone call, Leonard asks if Heather could help him get out of the asylum, and in turn he would give her the Seal and help stop Claudia. He requests she come to the "door at the end of the hall on the second floor", a door which wasn't there when Heather first explored the second floor. This door also leads to Brookhaven's Otherworld.
When she later encounters Leonard in the flooded basement of the Otherworld hospital, she has another short discussion with him, during which Leonard is hidden from view. Heather is dismayed to find that he too is a follower of the Order, just as Leonard is irate to learn she is a non-believer. Leonard refuses to part with his treasure, believing it his duty to protect the seal. He rises from the water and reveals himself to be a grisly monster, forcing an exasperated Heather to kill him.
After killing Leonard, Heather takes the Seal of Metatron. When Heather leaves the hospital, a scene of Claudia and Vincent is seen, in which Claudia angrily asks Vincent why he sent Heather to her father. Claudia also says, "It's your fault that he...!" but never finishes this, possibly implying she knew Heather killed him, perhaps as a result of omniscient powers. Vincent tries to pass it off as a good thing he died since he was one of "God's beloved", and he talks about Leonard's cruelty to Claudia as a child. Leonard is never mentioned again in the game or the entire series after this.
Leonard appears almost reptilian in nature, with a coat of sickly, yellowed skin covering him, almost like the victim of a drowning. His face is mutated and marred beyond recognition, only having a series of holes where his face should be. He has what appears to be black tongues or protrusions in some of the holes. His "hands", his most prominent feature, are a pair of huge blade-like bone growths which he uses to swipe at Heather Mason. He is amphibious, as he can last almost indefinitely underwater.
Leonard is quite aggressive; however, he spends much of the battle submerged underwater, crawling about out of Heather's attack range. The real challenge of the battle is the fact he is an astounding swimmer, something he does far more like a sort of porpoise than a human, as his arms remain tightly against his side as he bolts through the water. This can make it very difficult for Heather to actually reach him or even keep up with exactly where he is. He can nip at her ankles while he's underwater, but does no real damage. When he rises, however, he flails his blades about, able to do a great deal of damage to Heather in the process. He can also march towards her and slash at her, a problem compounded by the small fighting space. Fortunately, Leonard is much slower above water than when he is swimming, so his pace is nearly matched with Heather's, enabling it much easier for her to evade him.
He is very vulnerable to firearms, and the maul also works well. As Leonard is quite slow while standing, the player can sneak behind him fairly easily. An overhead smash with the maul from behind stuns him, momentarily forcing him down, making it possible to score up to four consecutive hits. The battle with him is more a matter of patience and caution.
It is not clear what Leonard's condition is. He may be a normal human who Heather sees as a monster. Another theory is that he was corrupted by his own madness and the Otherworld, and so became a monster representing his abusive nature towards Claudia. His large, swollen arms may represent that Claudia was physically beaten by them. He also may have died, and his soul reformed as a monster in the Otherworld. However, Claudia asks Vincent why he sent Heather to him, perhaps implying that he was still alive, just corrupted to the point of becoming a monster. Regardless, Heather notes that he is not a "person" anymore before killing him.
- Main article: Leonard Wolf (film)
Leonard Wolf also appears in the film Silent Hill: Revelation, both as a human and in monster form. As with the game, he is an ex-priest of the Order who holds the Seal of Metatron, and who was condemned to an asylum. In the film, there is no evidence that he was abusive towards Claudia, however, Claudia believes that he has been corrupted by the evil of Alessa Gillespie. He is portrayed by Malcolm McDowell.
- "Don't lie to me, Claudia. You're always trying to run from your responsibilities!"
- "How did you turn out this way... where did I go wrong?"
- "I can feel the hatred... behind your words. The anger. You plan to kill her, don't you?"
- "She's a fool... but she's still my daughter."
- "I'm not sure myself, but the door is at the end of the hall on the second floor."
- "Why must we reward even the unbelievers?"
- "It's true that God is merciful... but first, one must be chosen. Only we who hearken to the voice of God will be given the keys to Paradise! Don't you think so, Heather?"
- "You're an unbeliever? You deceived me!?"
- "So you tried to trick me so you could run off with my seal, eh? Heretic! You plan to destroy God!"
- "Don't play innocent. You can't fool me anymore. The seal is mine! I was appointed by God to be its guardian! The only thing you'll get from me is a gruesome death!"
- He is voiced by Matt Lagan.
- It is highly implied that Leonard is trapped in the Otherworld version of Brookhaven Hospital, possibly due to him once stabbing someone, as well as his child abuse of Claudia. It could be thought Silent Hill and its Otherworld is punishing him for his ways. Heather explores Brookhaven Hospital and is unable to locate him until she traverses to the Otherworld.
- In the Otherworld version of Brookhaven Hospital, an optional memo called the Day Room Notebook can be found that contains a diary entry most likely written by Leonard. It is covered with childish doodles depicting a figure wielding dual daggers, a winged sun (possibly representative of the Order's deity) and the bodies of the slain strewn about the ground. It gives the player an early clue as to Leonard's true nature and his belief that non-believers do not deserve salvation. It is also possible that the diary was written by Claudia as a young girl. However, the writer describes themselves as a "protector of the seal", and Leonard was the one who possessed it, while Claudia believed it to be "a piece of junk" and thought her father was foolish for keeping it, thus the notebook was most likely written by Leonard.
- Leonard is one of the few monsters that are conscious and can speak in their monstrous forms, the others being: Mary, Prisoners, Twin Victim, Bottom, Momma, Steel Guardian, Monocle Man, Alessa, Lucas, Ben, and Karen. Note that the Sad Daddy could speak only in its human manifestation.
- Defeating Leonard in under three minutes in the Silent Hill HD Collection awards the trophy/achievement "A Time to Kill".
- During the Leonard Wolf boss fight in the Silent Hill HD Collection, both Heather and Leonard are able to sprint full speed in the water as if the water doesn't exist.
- As Heather passes by a set of public phones in the subway, one of the phones begins to ring, before it is almost instantly cut off. It is never known who, or what, was trying to make the call. It can be theorized it is Leonard or the Happy Birthday Caller.