We present the case of a diabetic gentleman who was admitted to the hospital with an infected right foot. Swabs were positive for Staphylococcus aureus and Pseudomonas aeruginosa. His right big toe was amputated. Postoperatively, the patient experienced recurrent episodes of chest pain. He was therefore transferred to the coronary care unit, where he deteriorated rapidly. The patient was subsequently transferred to intensive care. Transthoracic and transesophageal echocardiograms revealed evidence of aortic dissection, but this finding was not confirmed in a computed tomography scan. The patient subsequently experienced cardiac arrest and died. The postmortem examination revealed no aortic dissection but did show a vegetation on the mitral valve with a fistula that tracked into a ruptured epicardium.