The Wheelman is the penultimate boss of Silent Hill: Downpour. This monster appears throughout the game in a much lesser form, cloaked in hospital garb, while taunting Murphy Pendleton. It is first seen by Murphy in the window of an abandoned house near Devil's Pitstop.
The Wheelman resembles a giant, emaciated corpse fused with a wheelchair and life-support machinery. The underside of the ribcage/stomach area is largely exposed and has numerous tubes and machinery plugged into it. It also has plentiful segments of wire and metal fused into its body. Its face is completely mutilated into a pulpy mass, with a horribly tumor-like growth on one half of its face and a single skinned eye on the other half. It has skinny, atrophied legs which seem to be tied to its wheelchair and can only be seen when it writhes in pain. Huge tanks of blood surround its environment, as well as clear fluids and gigantic air-pumps.
The Wheelman is a massive creature, and Murphy has no way of confronting it directly. In order to damage it, Murphy must forcefully remove all four of the huge life support hoses attached to the scaffolding around it. If Murphy tries to remove them without first distracting the Wheelman, then he'll interrupt Murphy by violently slamming its fist down on him. It will also do this as Murphy tries to cross large sections of the catwalk. Murphy must ride up on top of the air pumps like elevators and blind the Wheelman by pointing a spotlight in its eye, giving him an opportunity to ride back down and remove the hoses.
The Wheelman has a few methods of attack, other than the aforementioned fist slams. It seems to have telekinetic powers, as it creates distortions in the air and gathers loose debris in a cluster before hurling it at Murphy's current location. A shotgun blast will disrupt it and cause it to drop its current collection, however. It also rips open cells to free other monsters should Murphy retreat out of its sight. Its last, although seemingly unintentional, attack is to summon forth huge bolts of lightning on Murphy's location when it starts raining. While it does this it flails and sparks, obviously being shocked violently by its life support during the downpour.
The Wheelman is a manifestation of the memory of Frank Coleridge, and taking into consideration the fact that Murphy must pass through a door with the Scales of Justice hanging above it, then it may also represent Murphy's feelings of guilt and responsibility over the role he played in Frank's death.
It is possible that the Wheelman represents Murphy's conscience as well. Because the image of Frank Coleridge frequently appears in Silent Hill as a manifestation of Murphy's conscience and good nature, the monster's deteriorated state could embody the erosion of Murphy's morality based on the poor choices he made following the death of his son, Charlie Pendleton.
Anne Marie Cunningham mentions that when her father, Frank, was brutally beaten, he survived the attack but went into a vegetative state and was confined to a wheelchair. She goes on to say that when she looked at him in this state, she saw a monster, or, in this case, Murphy Pendleton. Because of this it's possible that the Wheelman is actually a manifestation of Anne's psyche, as opposed to Murphy's, showing the deterioration of her father and role-model as well as her desire to avenge his death.
- Wheelman is the one responsible for all the wheelchairs found throughout the game, like the one on top of the gas station in the beginning of the game, the one blocking the library elevator, etc. This is because of Frank's affiliation with them.
- This may be a reference to past Silent Hill games, as wheelchairs appeared in most of them, even being featured as enemies in Silent Hill 4: The Room.
- The boss highly resembles both the appearance and sound effects of the titular humanoid featured in "Rubber Johnny", a music video directed by Chris Cunningham for musician Aphex Twin. During an interview, "Rubber Johnny" was confirmed as a direct influence. It should be noted that the director of the video shares the surname of Anne Cunningham, the daughter of the man who the boss reflects in-game. 
- The Wheelman is seen numerous times by Murphy prior to the boss fight, most which are inevitable, however one in particular can only be found by the player's choice. Through a set of binoculars at Devil's Pit's observation deck, Murphy can see the Wheelman slowly pushing himself along a boardwalk, which prompts Murphy to comment "I must be going crazy...". It also begins to pour down rain with the accompaniment of thunder and lightning, something very reminiscent of the final boss fight.