Heart valve replacement is a common cardiac surgical procedure used to treat native valvular diseases such as aortic and mitral stenosis and regurgitation. These procedures reduce the morbidity and mortality associated with diseased native valves and yet come at the expense of prosthetic valve complications. Structural valve degeneration is one such complication. We present a case of a critically ill elderly man who had undergone mitral valve replacement 14 years prior to his current presentation. Only after admission through the emergency department was a transesophageal echocardiogram obtained and the diagnosis of prosthetic valve degeneration made. He subsequently underwent successful replacement of his diseased prosthetic valve.