A 19-year-old male presented with recurrent fever and weight loss for 10 months. He has a history of bicuspid aortic valve with severe aortic regurgitation. On examination, he appeared ill with clubbing and multiple pigmented lesions. Tests found anemia, elevated inflammatory markers, and Enterococcus species in blood cultures. Echocardiography showed vegetation on the aortic valve with worsening of valve abnormalities and cardiac function. The final diagnosis was infective endocarditis in the setting of a bicuspid aortic valve with severe aortic regurgitation.