A 57-year-old male with schizophrenia and a 37 pack-year smoking history presented with cough productive of purulent sputum associated with hemoptysis and worsening shortness of breath. Computed tomography (CT) scan revealed multiple masses in the right upper and lower lobes with a small distal tracheal mass and significant mediastinal lymphadenopathy. CT guided biopsy of the largest lung mass in the right lower lobe confirmed a diagnosis of pulmonary actinomycosis. The patient received appropriate antibiotic therapy for four weeks, but his condition did not improve. A repeat CT scan showed worsening of the right lung consolidation with increasing occlusion of the trachea. Bronchoscopy was performed which revealed a friable necrotic mass occupying 70% of the tracheal lumen. Histopathology showed squamous cell carcinoma of the trachea likely of primary origin. Unfortunately, the patient was not a candidate for any surgical intervention or oncologic treatment, and he died few days later. This patient had a rare simultaneous presentation of both pulmonary actinomycosis and tracheal squamous cell carcinoma. To the best of our knowledge, this is the first reported case of simultaneous diagnosis of both conditions in the same patient. This case illustrates the importance of looking for an alternative diagnosis in patients with actinomycosis who do not respond well to appropriate therapy.