A 19-year-old young woman presented with fever, complicated pleural effusions, and bilateral lung infiltrates following an episode of sore throat 7 days ago. Ultrasound examination revealed the presence of a thrombosed left internal jugular vein, suggesting the diagnosis of Lemierre syndrome and the patient was successfully managed on a combination of meropenem, linezolid, and metronidazole. Blood and pleural fluid cultures remained sterile. Long-term therapeutic anticoagulation was commenced and although she failed to achieve therapeutic targets as an outpatient, we observed an almost complete resolution of the clot on a follow-up visit 6 weeks later. This is a case with several distinguishing features of Lemierre syndrome, namely, the heralding symptom of sore throat and the culmination to severe pneumonia due to multiple septic emboli originating from a thrombosed internal jugular vein. Fusobacterium necrophorium is the most common culprit. However, the disease is often polymicrobial; and most authorities advocate a combination of antibiotics for its treatment. On the other hand, therapeutic anticoagulation might not be necessary.