Recognizing the treatment factors that will increase the predictability of regenerative surgical procedures may encourage periodontal treatment of apparently hopeless teeth. This case report describes the longterm clinical outcome of a periodontal (15 mm of clinical attachment loss) and bone defect associated with a periapical lesion affecting a maxillary lateral incisor in an esthetically demanding, systemically healthy young patient. Treatment procedures comprised endodontic treatment of the periapical lesion and cause-related therapy aimed to eliminate bleeding on probing and control the infection in the rest of the mouth. Four months later, a regenerative surgical technique combining the simplified papilla preservation approach, application of enamel matrix proteins and bovine porous bone mineral, and a coronally advanced buccal flap at the adjacent teeth in the surgical area was performed. Clinical examination at the 1-year recall revealed clinical attachment gain (8 mm) with shallow residual probing pocket depths (3 mm) and a slight (1 mm) increase in gingival recession. The esthetic appearance of the treated tooth was improved via the addition of odontoplastic and resin composite. Three years postsurgery, both the esthetics and the periodontal health were fully maintained. The present case report suggests that successful periodontal and esthetic results can be accomplished and maintained for at least 3 years after regenerative treatment of an apparently hopeless tooth with extremely severe baseline periodontal conditions.