A 57-year-old patient presented with a long history of minimally symptomatic mitral valve prolapse (MVP). The patient eventually developed severe mitral regurgitation (MR) and clinical evidence of congestive heart failure over 10 years duration before admission. He described a 34-year history of MVP. A transesophageal echocardiography examination demonstrated left atrial enlargement and severe prolapse of the posterior mitral leaflet associated with severe MR to the dome of the left atrium. Left ventricular size and function were normal. A quadrangular resection of prolapse segment and placement of a posterior annuloplasty ring were used to successfully repair the valve using a minimally invasive approach. The current case emphasizes that patients with MVP complicated by MR may remain clinically asymptomatic for prolonged periods, only to subsequently develop left atrial enlargement, severe MR, and congestive heart failure late in the natural history of the disease.