A previously healthy 10-year-old patient with headache, otalgia, and hearing loss was diagnosed with pachymeningitis and methicillin-resistant Staphylococcus aureus otitis media and bacteremia. Despite antimicrobial therapy, intracranial extension progressed, including clival osteomyelitis, sphenoid sinusitis, cavernous sinus inflammation and cranial nerve palsies, until the sphenoid sinus was drained. This case exemplifies an aggressive MRSA intracranial infection that advanced despite antibiotic therapy.