Aortic dissection is an uncommon yet frequently fatal illness. Patients generally present with tearing chest pain with possible acute hemodynamic instability. Hence, early diagnosis and intervention is critical for survival. This is a case of a 62-year-old male who was transferred to our emergency department for severe chest pain, left side hemiplegia, left hemianopsia, left facial weakness, suggesting a right-sided stroke. A chest computed tomography angiogram showed an extensive circumferential aortic dissection of the intimal layer involving the great vessels. Antiplatelet medications were withheld, nicardipine was started, and the cardiothoracic surgeon was consulted. There was no indication for surgery, and patient was admitted to the intensive care unit. We highlight here the importance of considering an aortic dissection in patients who present with neurological symptoms and an acute history of tearing chest pain.