We report a case of fatal duret hemorrhage (DH) in a patient with acute tentorial subdural hematoma and bilateral chronic subdural hematoma along the cerebral hemispheres. Preoperative CT angiography (CTA) revealed prominent parenchymal enhancement in the ventral pontomesencephalic area. After burr-hole drainage, a large hemorrhage developed in this area. The parenchymal enhancement in the CTA may reflect the pontomensencephalic perforating vessel injury, and may be a sign of impending DH of acute transtentorial downward herniation. Previous use of aspirin and warfarin might have potentiated the process of DH and increase the extent of the bleed.