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Infective endocarditis (IE) is an infection of the endocardium that involves valves and adjacent mural endocardium or a septal defect. Local complications include severe valvular insufficiency, which may lead to intractable congestive heart failure and myocardial abscesses. If left untreated, IE is generally fatal. Diagnosing IE can be straightforward in patients with the typical oslerian manifestations such as bacteremia, evidence of active valvulitis, peripheral emboli, and immunologic vascular phenomena. In the acute course, however, the classic peripheral stigmata may be few or absent, particularly among intravenous drug abuse (IVDA) patients in whom IE is often due to a S. aureus infection of right-sided heart valves. We present a complicated case of a very aggressive native aortic valve MSSA (methicillin sensitive Staphylococcus aureus) IE in a young adult male with a past medical history of bicuspid aortic valve and IV drug abuse. His clinical course was complicated by aortic valve destruction and development of third-degree AV block, as well as an aorto-left atrial fistula requiring emergent operation for AV replacement and patch repair. The patient required two reoperations for recurrent endocarditis and its complications.