Fusiform dilation of the jugular vein, or jugular venous phlebectasia, is a rare clinical entity, with an etiology of cervical swelling. We present a case of a 15-year-old male with no antecedent history of trauma and an enlarging right neck mass. Pertinent literature and relevant diagnostic and therapeutic modalities are reviewed. While conservative management is usually prescribed, ligation and resection may be performed safely when intervention is warranted.