Libman-Sacks endocarditis is a rare cardiovascular manifestation of systemic lupus erythematosus. It is described as sterile vegetative lesions which can damage heart valves resulting in complications such as acute coronary syndrome and heart failure and can embolize to cause cerebral and renal infarcts. We present the case of a young African American female presenting with pleuritic chest pain. She was initially admitted for acute coronary syndrome. She was later found to have severe mitral regurgitation and eventually received a transesophageal echocardiogram which confirmed the diagnosis of Libman-Sacks endocarditis. Her course was complicated with acute diastolic heart failure and several embolic strokes in the watershed anterior cerebral artery/middle cerebral artery (ACA/MCA) territories. She was started on anticoagulation and antiplatelet agents. Her underlying lupus was treated with immunosuppressive agents. This case demonstrates that a high index of suspicion for Libman-Sacks is crucial in patients with lupus if presenting with cardiovascular symptoms. Early and prompt diagnosis can prevent and lessen the many side effects associated with thromboembolism.