A 53-year-old woman with no past medical history presented to the Emergency Department with right frontal headache and ipsilateral neck pain. She was found to have right internal jugular vein thrombosis, right cerebellar stroke, meningitis, septic pulmonary emboli, and fusobacterium bacteremia, all consistent with a severe presentation of Lemierre’s syndrome (LS). While LS is often preceded by nasopharyngeal infection, no such history was elicited from our patient. Instead, concomitant papillary thyroid cancer with extension to her right internal jugular vein was implicated. Prompt recognition of these multiple related processes led to a timely initiation of appropriate therapy for infection, stroke, and malignancy.