Stenosis or occlusion of the brachiocephalic artery represents an uncommon cause of cerebrovascular insufficiency. We report a patient with combined brachiocephalic and left subclavian obstruction with clinical manifestations of lightheadedness, syncope, and left-sided weakness who remained misdiagnosed essentially because of symmetrical pressures in the upper extremities. Aortic valve replacement for aortic stenosis failed to provide symptomatic relief. Eventual stenting of the brachiocephalic trunk resolved the patient's symptoms. Our report highlights the diagnostic challenges in this case of bilateral supraaortic vessel disease and shows that equal upper extremity pressures do not rule out brachiocephalic artery obstruction.