Introduction: Phlegmon is an acute, rapidly spreading, suppurative inflammation of the connective tissue characterized by diffuse involvement without clear anatomical boundaries. When it affects the floor of the mouth, particularly the submandibular and sublingual spaces, it is referred to as Ludwig’s angina, a severe deep neck infection most commonly originating from odontogenic infections of the second or third mandibular molars. Ludwig’s angina is potentially life-threatening because of the risk of sudden airway obstruction and rapid progression to serious complications, including mediastinitis, pulmonary infection, sepsis, multiorgan failure, and death. Despite advances in antimicrobial therapy and surgical source control, airway compromise and infectious complications remain major challenges. Case Description: A 35-year-old man with bilateral submandibular abscesses who underwent incision, drainage, and tracheostomy at a referring hospital. Three days postoperatively, the patient developed pneumonia with purulent discharge from the tracheostomy site. Imaging revealed the extension of the infection into the parapharyngeal and retropharyngeal spaces, requiring repeat surgical debridement. Following surgery, the patient was admitted to the intensive care unit (ICU) and required mechanical ventilation. The ICU course was complicated by right-sided pleural empyema necessitating thoracotomy with decortication and chest tube placement, as well as ventilator-associated pneumonia caused by multidrug-resistant organisms. Management involved aggressive source control, advanced airway management, broad-spectrum antimicrobial therapy, optimized nutritional support and intensive respiratory physiotherapy. Conclusion: This case underscores the complexity of managing severe Ludwig’s angina complicated by sepsis and ventilator-associated pneumonia. Early recognition, prompt surgical intervention, meticulous airway management, and comprehensive multidisciplinary intensive care are crucial for improving outcomes in patients with extensive deep neck infections and critical respiratory complications.