We describe the case of a 45-year-old man with a unique constellation of supra-aortic artery aneurysms detected by chest X-ray during work-up for chronic cough. During his diagnostic work-up, the patient suffered an embolic stroke likely secondary to disrupted plaque originating in an aneurysmal right vertebral artery. Endovascular repair was not a viable option due to the diffuse and bilateral nature of aneurysmal disease, including involvement of the innominate and right carotid and vertebral arteries. The patient was successfully treated with a two-stage open surgical approach involving an initial right carotid artery to vertebral artery bypass and subsequent in situ reconstruction utilizing a bifurcated Dacron graft sewn to the proximal aortic arch with distal extension to the right common carotid and axillary arteries.