Lemierre's syndrome is an acute oropharyngeal infection with a secondary septic thrombophlebitis of the internal jugular vein (IVJ) that was first reported in literature in 1936. It involves the progression of disease from a focal suppurative peritonsillar infection to a local septic thrombophlebitis with hematogenous progression to and distant septic emboli. It is a rare and potentially fatal syndrome requiring prompt diagnosis and management. We present the case progression of an 18-year-old male who presented to our hospital with resolved sore throat, fever, and chest discomfort who experienced a sharp clinical decline. His case, physical exam, laboratory abnormalities, and radiologic studies highlight important facets of this rare but important syndrome.