A 55-year-old female with hypertension presented to our facility with complicated pneumonia. She complained of progressively worsening shortness of breath and pleuritic chest pain. She was in her usual state of health except for an upper respiratory infection treated with oral antibiotics a month prior. At the presentation, she was febrile, tachycardic, and hypoxic on room air. A chest computed tomography (CT) showed near-complete opacification of the right lung, a cavitation with the fluid level in the right middle lobe, and moderate-to-large effusion. Broad-spectrum antibiotics were started. Sputum culture was later positive for methicillin-resistantStaphylococcus aureus, which prompted antibiotic de-escalation to vancomycin. A chest tube was placed into the right pleural space draining 700 mL of exudative fluid, which cultures grewStreptococcus anginosusgroup (SAG) bacteria. Due to persistent respiratory distress and residual effusion, right thoracotomy and decortication were performed. A right upper lobe abscess ruptured into the pleural space was noted during the procedure. Pathology revealed necrotic tissue, and the microbiological workup was negative. The patient clinically improved postoperatively and was discharged home with oral Linezolid.