Patients with a history of drug abuse and right sided endocarditis are prone to develop septic pulmonary emboli. Pneumothorax is a rare complication of septic pulmonary emboli reported in the literature, likely due to the rupture of thin-walled septic cavitary lesions resembling pneumatoceles into the pleural space. Only seven cases (including our case) of pneumothorax from septic pulmonary emboli due to right sided endocarditis have been described in the literature. Our patient is the first reported case of recurrent bilateral pneumothorax due to septic pulmonary emboli and tricuspid valve endocarditis.