Pituitary adenomas are one of the most common intracranial tumors. Non-functioning macroadenomas are usually diagnosed when they cause symptoms due to the mass effect on surrounding structures. We present the case of a 48-year-old man who presented with a headache associated with ptosis of the right eye and right-sided blurry vision for three days. Initial computerized tomography (CT) scan of the head did not report a mass, acute infarct, or hemorrhage. He was given 325mg of aspirin for concern of a stroke while waiting for magnetic resonance imaging (MRI) of the brain, which was done the next day and revealed a pituitary macroadenoma with hemorrhage, mass effect, and compression of the optic chiasm consistent with pituitary apoplexy. He ultimately underwent trans-sphenoidal resection of the tumor; however, his surgery was delayed for five days as he had received a high dose of aspirin in the Emergency Room. His adrenocorticotropic hormone (ACTH), cortisol, and testosterone levels were found to be quite low. He was administered stress dose steroids peri-operatively and ultimately discharged on indefinite hydrocortisone therapy and endocrinology follow-up. Our case highlights a serious complication of pituitary adenomas that can occur called pituitary apoplexy which is caused by acute ischemic infarction or hemorrhage in the pituitary. It needs prompt identification and management. Our case also emphasizes the importance of recognizing pituitary apoplexy as one of the causes of sudden onset cranial nerve deficits, as it is a rare presentation of pituitary adenomas that can be taken for a stroke in the Emergency Department.