Streptococcus intermedius is a Gram-positive commensal of the oral cavity with tendency to cause brain and liver abscesses. Mediastinal involvement from S. intermedius is very rare. We present a case of 22-year-old male with newly detected mediastinal conglomerate nodal mass. On his way for bronchoscopy, he developed seizures and was found to have three brain lesions. The aspirate from brain biopsy grew S. intermedius whereas the aspirate from mediastinum showed only acute inflammation. Follow up imaging after antibiotic treatment showed interval resolution of brain abscesses and the mediastinal mass. We believe that the patient had aspiration pneumonia from S. intermedius which then metastasized to mediastinum and brain. Our aim is to make physicians aware of this unusual presentation of S. intermedius infection as a mediastinal mass. A strong effort should be made to isolate the organism from the involved body sites and fluid cavities to confirm the diagnosis.