Complications arising from internal jugular venous catheterization are uncommon. Injury to the carotid artery is reported as one of the more common injuries. Vertebral artery injuries are rare and include pseudoaneurysm formation, arteriovenous fistulas, lacerations, and dissection with thrombus formation. Occasionally, such injuries initially go unnoticed and have the potential to cause catastrophic outcomes, leaving clinicians and families wondering what transpired. A thorough autopsy can not only help discern the cause of death, but also help to bring closure to the family. Here we present a case of an unexpected death 3 days following surgery for idiopathic scoliosis in a 17-year-old male. During the surgical procedure, a right internal jugular venous catheterization was attempted but aborted after several failed tries. Twenty-four hours after the procedure, the patient became obtunded and progressed to brain death. At autopsy, he was found to have a right transmural vertebral artery puncture wound with thrombosis leading to a massive posterior circulatory stroke.