Background: Familiarity breeds complacency. One case of sore throat can start to sound like another. However, even common viral and bacterial infections can lead to serious sequelae. Clinicians cannot make a diagnosis if they do not consider it in their differential. Case: The presentation -- and subsequent hospitalization -- of a septic 19 year-old male college student is described. Despite brief interval improvement, he became hypoxic one week after developing a sore throat and was ultimately diagnosed with Lemierre's syndrome (septic thrombophlebitis of the internal jugular vein) via blood cultures and advanced imaging. Conclusions: Though rare, Lemierre's syndrome carries a high mortality rate. It should be considered an emergent complication of head and neck infections, particularly in young adults.