This case report concerns a patient with fracture and primary dysfunction of a prosthetic valve. A 40-year-old man presented to the Emergency Department with a chief complaint of breakthrough pleuritic back pain and shortness of breath. Past surgical history was significant only for an aortic valve replacement and mitral valve replacement performed 16 years prior. The transthoracic echocardiography raised suspicion of prosthesis malposition. The patient was taken to the operating room by cardiothoracic surgeons for valve replacement. Operative findings revealed that a prosthetic valve leaflet in the mitral position had broken off. Primary prosthetic valve failure should not be overlooked in the differential diagnosis of patients with valve replacement and a rapidly deteriorating clinical course. Emergency echocardiography is a guide to convenient diagnosis and management. Early surgical consultation and early reparative surgery might prevent unnecessary morbidity and mortality.