Spontaneous esophageal perforation or Boerhaave's syndrome is an uncommon condition that may occur following forceful vomiting and lead to mediastinitis. It is associated with high mortality and morbidity in absence of therapy. We present a case of spontaneous esophageal perforation in a 63 year-old man who developed a right-sided effusion, an unusual presentation. This case report and the relevant literature reveal that delay in prompt surgical repair is associated with a high morbidity and mortality.