This article describes a woman in her forties who spontaneously developed facial pain 19 years after double-jaw orthognathic surgery. The focus of her pain was the left side of the face, including the temporomandibular joint (TMJ). Conservative treatment was initiated, including several occlusal splints, in addition to injections with local anesthesia, botulinum toxin, and corticosteroids, with limited effects. Surgical treatments with arthroscopy and discectomy, and ultimately a TMJ prosthesis, improved the patient’s joint function but did not reduce pain. The question is whether the degenerated joint was due to progression of the original disease process or to multiple surgical procedures.