This study presents a case of a 15-year-old boy who had a right vertebral artery dissection with distal embolization from repeated trauma from an occipital bony spicule. The authors hypothesize that this bony spicule was contacting the left vertebral artery during head rotation, resulting in trauma to the vessel and formation of emboli which then showered distally, causing strokes in the posterior circulation of the brain. This specific phenomenon has previously been reported three times, only one of which was in pediatric literature. It is important for individuals to be aware of this rare anatomic cause of vertebral artery dissection in patients presenting with an odd constellation of symptoms related to strokes from vertebro-basilar system. Treatment options including early intervention with intravascular coil embolization are also discussed.