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|“|| Thank God, you're alive. I was about to go looney tunes in this roach motel!
Despite being a police officer, as seen in his diary, Wheeler is fairly suspicious, skeptical, or even paranoid, and has conspiracy theories such as cell phones being listened to by any number of shadow organizations, the Moon landing being fake, chemtrails, the Trilateral Commission, and the American government being behind global warming. Although distrustful, Wheeler maintains a notable sense of wry humor.
Silent Hill: Homecoming
Though Wheeler appears to be fairly eccentric, he is open-minded to Alex's attempts to convince him that Sam Bartlett died, that Alex was not his killer and even when Alex makes mention that it was a creature that killed the Mayor, remarking, "So you've seen the creatures too...". First encountered in Shepherd's Glen Police Station, Wheeler immediately teams up with Alex and attempts to assist him and Elle Holloway as they make their way to Silent Hill. However, Alex and Wheeler are soon separated by a Siam attack.
When Alex escapes from the Hell House, Wheeler assists him by boating him to Silent Hill. On the way, Wheeler and Elle are abducted by Order Soldiers, and Alex is knocked unconscious in the scuffle. When Alex reawakens, he discovers that the Order has imprisoned Wheeler in the Overlook Penitentiary. It turns out that the Order failed to confiscate his walkie-talkie, and so Wheeler guides Alex through Silent Hill and the prison until he is eventually rescued in his prison cell by Alex. Later on, Wheeler and Alex find Margaret Holloway in the Otherworld prison, but Wheeler is abducted by Asphyxia before they have a chance to get information from her.
Later on, Wheeler is found in the Lair of the Order, strapped to a chair with multiple knives embedded in his chest. At this point, his life is put in the hands of the player, when Alex is given the choice to save Wheeler's life with a medical pack or to keep it for himself. It's unclear what becomes of Wheeler should Alex choose to save him; it's only suggested he survives the ordeal and lives to tell the tale. If he is saved, Alex tells Elle to leave the Lair with Wheeler.
During the UFO Ending, Wheeler is seen coming out of the building as Alex and Elle are beamed up into the spacecraft, which prompts him to say, "So that's where they've been taking everybody. I knew it!".
- "Open your eyes! You open your eyes, you might just start seeing what’s really going on in the world."
- "So all I can say right now is that I know things. I know about things that maybe you know about, maybe you don’t. Either way, it’s not my job to convince you that you’ve been lied to. It’s my job to make you question what you’ve been told. Only then can we start to REALLY understand what’s going on around here."
- "I didn't always used to think like this. I was a skeptic, same as most people. But then I came here. In the last few years, I've seen more strange shit than most people have seen in their whole lives. I started thinking that maybe there might be other people like me out there. People who QUESTION things."
- "Things are not right here. This isn't something I'm making up. There is something honest-to-God wrong with this place."
- "So I'll leave you with this, people. Learn from what's happened to me, because it could happen to you. Open your eyes to what's going on around you. Whoever did this here could do it in your town too. PAY ATTENTION. And don't believe the people in power when they say that everything is going to be okay. Because it's not."
Silent Hill: Homecoming
- "Well, well. Back in the world of the living."
- "You won't be going anywhere, until I get some answers."
- "Alex, I can believe an awful lot, you just gotta trust me."
- "So you've seen the creatures too..."
- "Shit! We ain't goin' that way!"
- "They all know a helluva lot more than they're letting on, and I'm sick of being in the dark."
- "Clear a path through the lobby and break down the barricade. I'll cover you."
- "Hey, I've been better, but I'm OK."
- "Hell, you're not getting rid of me that easy."
- "Silent Hill is what I mean. The place has bad history. Always has."
- "I guess there's some sort of irony here."
- "When this is over, I'm buying the first round, and then the second."
- "I can walk, run, fly... shit, I may be a little slow, but whatever the hell it takes to get out of here, let's do it."
- "You cuff' him. I'll read him his rights."
- "Now THAT's gross."
- "Let's go, partner."
- "So that's where they've been taking everybody! I knew it!" (Wheeler in the UFO ending)
- Wheeler is the fourth character with African-American heritage seen in the Silent Hill series (the first three being Toby Archbolt of Silent Hill 4: The Room and Bill and Jessie of Silent Hill: The Arcade).
- Wheeler's first name "James" is never mentioned in the game. It is only mentioned in concept art and in unused game files. He shares the first name of James Sunderland, the protagonist of Silent Hill 2, and it is possible the developers named Wheeler after James as a homage.
- Wheeler is the second character in the main series who can help the player fight in combat, after Eileen Galvin.
- The player can unlock a costume for Alex that resembles Deputy Wheeler's uniform.
- Wheeler appears to be extremely lucky, as he's put in several dangerous situations but always manages to pull through, unless the player chooses otherwise.
- Wheeler's physical appearance resembles that of actor Forest Whitaker, including the drooped eyelid condition known as ptosis.
- Alex's father told Wheeler when he first came to Shepherd's Glen that he would never have to go to Silent Hill. He found this to be ironic, as later he takes a boat out to Silent Hill with Alex and Elle.
- During the boat ride, Deputy Wheeler mentions a missing female police officer who is heavily implied to be Cybil Bennett from Silent Hill.
- When Alex gets a call from Wheeler over the radio (assuming that Elle is still in possession of it) after exiting the junk yard, Alex informs the deputy of who he is, to which Wheeler responds: "Alex Shepherd? But I thought you were..." The transmission is then lost due to the appearance of a Smog for the first time. The above may signify that Wheeler knew the truth of Alex's departure, but it's not made clear if this is the case. However, the existence of a photo of the deputy and Adam Shepherd on a boat could mean that two were good enough friends for Adam to have told Wheeler the truth of Alex being committed to a mental institution. He may have also believed that Alex was disappeared/deceased based on his sudden departure, along with the rest of the residents of Shepherd's Glen, as he mentions to Alex upon meeting him that he's "back in the world of the living".
- In the prison, in the cutscene where a Siam attacks Alex and Wheeler, it can be noted that Wheeler is wielding a revolver. However, in the actual fight, he wields a semi-automatic.
- Removing the five knives from Wheeler's chest (which Alex does if the player saves him), in a real-life situation, is not recommended because it may cause further bleeding or open damaged arteries.