W. Somerset Maugham’s Pacific short fiction, seen in The Trembling of a Leaf (1921), is filled with murders, suicides, and mental and emotional crisis. White characters, doing the footwork in imperial structures, experience collapse under the weight of their ‘illegitimate privilege’ (Memmi), especially in the famous story “Rain,” and the lesser known “Mackintosh.” In “Rain,” Maugham highlights differences over sexuality and the body in the lives and actions of a missionary and a sex worker. Just as the missionary in “Rain” experiences a moral and personal collapse, so the administrator in “Mackintosh” undergoes a mental crisis, when facing the actions of his brutal colonial overseer. This induces a peculiar form of madness inspired by moral injury in the face of the imperial power’s mundane violence. These personal implosions are also ascribed to the tropical environment, long equated in the European imagination with degenerative effects, immorality, and the Primitive. The combination of tropicality and illegitimate privilege is seen to coalesce in the late-imperial moment to bring about internal disintegration in white characters in the Pacific.