We report the case of a young patient with meningovascular syphilis who suffered fatal vertebrobasilar occlusion despite thrombolytic treatment and endovascular interventions. A 35-year-old man without any known medical history presented with an acute ischemic stroke and was initially treated with intravenous tissue plasminogen activator. He was then transferred to the stroke center, where he underwent endovascular recanalization of his occluded vertebrobasilar system. Despite initial successful recanalization, he suffered recurrent vertebrobasilar occlusion, and a second endovascular treatment attempt was unsuccessful. He subsequently developed a pontine hemorrhage and acute hydrocephalus and died secondary to transtentorial herniation. Laboratory findings were suggestive of prior spirochetal infection, and autopsy revealed necrotizing vasculitis and extensive adventitial inflammation involving the basilar and vertebral arteries, supporting the diagnosis of meningovascular syphilis.