Maloney dilatation of the esophagus is rarely associated with esophageal rupture. An 82-year-old man underwent routine upper endoscopy followed by esophageal dilatation, which was complicated by severe esophageal disruption and mediastinitis. One possible mechanism is gastric dilatation with obturation of the distal esophagus causing excessive pressure at the gastroesophageal (GE) junction. Endoscopy should always be followed by gastric air removal before introducing esophageal dilators.