We present a patient with a distinctive lesion of the skull base, which, at imaging, showed expansile destruction of the sphenoid bone, hemorrhage with fluid-fluid levels, and contrast enhancement of a solid portion. These features ordinarily suggest either giant cell tumor or aneurysmal bone cyst; however, pathologic examination confirmed instead a rare variant of osteosarcoma of the telangiectatic type. Although imaging findings can indicate any of these possibilities, biopsy is an essential step in arriving at the diagnosis.