Diabetic foot infections are a common cause of morbidity and mortality in the United States, and successful treatment often requires an aggressive and prolonged approach. Recent work has elucidated the importance of appropriate therapy for a given severity of diabetic foot infection, and highlighted the ongoing risk such patients have for subsequent invasive life-threatening infection should diabetic foot ulcers fail to heal. The authors describe the case of a man with diabetes who had prolonged, delayed healing of a diabetic foot ulcer. The ulcer subsequently became infected by methicillin-resistant Staphylococcus aureus (MRSA). The infection was treated conservatively with oral therapy and minimal debridement. Several months later, he experienced MRSA bloodstream infection and complicating endocarditis. The case highlights the ongoing risk faced by patients when diabetic foot ulcers do not heal promptly, and emphasizes the need for aggressive therapy to promote rapid healing and eradication of MRSA.