Untreated hypertension is highly prevalent and an important risk factor for hemorrhagic stroke and aortic dissection. Aortic dissection masquerading as ischemic stroke is practically challenging. We report a patient who initially presented as having a hemorrhagic stroke, following with ischemic stroke several days later and was finally discovered to have aortic dissection. The patient underwent craniectomy, ventriculostomy catheter installation, osmotic diuretics, analgesia, and sedation to maintain ICP within the acceptable range. Our therapeutic goal of blood pressure is the lowest level commensurate with adequate cerebral and vital organ perfusion. Although very rare, we should always remind ourselves that aortic dissection may occur after a hypertensive hemorrhagic stroke, and then present simutaneously with ischemic stroke as in our case.