A billionaire entrepreneur who bought and renovated the Overlook Hotel after World War II. Derwent throws the masquerade ball on the August night in 1945 that perpetually unfolds in the hotel’s ballroom, and when Jack finally goes insane and gets drunk in the Colorado Lounge, Derwent is there teasing one of the ball’s guests, Roger—who is dressed in a dog costume—with liquor. Jack first learns about Derwent when Ullman hires Jack as the hotel’s winter caretaker, but Jack really learns about Derwent when he goes through the boxes in the basement and finds a scrapbook documenting the Overlook’s history. Derwent has known mob connections, and he is also involved in bootlegging and prostitution. Presumably, Derwent is still alive during Jack’s time (1975), as Jack asks Al Shockley if Derwent is still involved in the hotel. Al refuses to answer. Derwent represents the Overlook Hotel’s seedy underbelly and is part of many of its scandals, including the “gangland-style shooting” in the Presidential Suite in 1966 and the murder of Vittorio Gienelli.