Massive pulmonary gangrene is a rare complication of pneumonia, particularly in the postantibiotic era. We report two cases of community-acquired Streptococcus pneumoniae pneumonia in young patients with a background of heavy alcohol abuse, but no other preexisting disease, which failed to respond to appropriate antibiotic therapy and intensive care. In both, there was extensive unilateral involvement, with initial dense consolidation followed by cavitation, but the previously reported classic later radiologic feature of coalescence into a large cavity with free-floating slough was not seen. Owing to ongoing sepsis with the development of multiple organ failure and the obvious failure of appropriate medical therapy, both patients underwent pneumonectomy with a successful outcome. These cases serve to emphasize the role of surgery in the management of massive pulmonary gangrene.