Once coined the "Forgotten Disease," Lemierre's syndrome is a rare condition that results from oropharyngeal infection with the gram-negative, anaerobic Fusobacterium necrophorum. The typical progression of illness involves spread to adjacent structures such as the internal jugular vein with resulting thrombophlebitis. Septic emboli to distant sites are also a common sequela. Here, we present a case of Lemierre's syndrome in a 20-year-old, otherwise healthy, male. The patient presented with fever, sore throat, and dysphagia. Imaging revealed peritonsillar multiloculated fluid collections and necrotizing pneumonia with multiple pulmonary abscesses. The patient's hospital course was complicated by the development of necrotizing fasciitis in his right lower leg, which required incision and drainage with surgical washout. In addition to systemic intravenous antibiotics and anticoagulation, he underwent multiple thoracentesis procedures. The patient was ultimately transferred to a tertiary care center due to persistent fevers and lung abscesses. This case highlights the challenges of initial diagnosis, as well as the treatment choices faced by the attending physicians.