We describe a 54-year-old male with history of type II DM, hypertension and dyslipidemia during admission for bronchopneumonia discovered to have coarctation of the aorta and a persistent left superior vena cava (PLSVC) draining into the left atrium through the left superior pulmonary vein. The latter was thought to contribute to a transient ischemic attack and an episode of chest pain resulting in ST-segment elevation in the inferior leads. He was treated with coarctation stenting and percutaneous exclusion of the PLSVC with a vascular plug.