An 85-year-old man presented to an outside hospital with 2 weeks of progressive vague chest discomfort and worsening shortness of breath. Upon presentation he was septic, with fever, tachypnea, and tachycardia. Chest radiograph showed a large spontaneous left-sided pneumothorax with a large pleural effusion. A left chest tube was placed, and he was fluid resuscitated, placed on vasopressors and broad-spectrum antibiotics, and transferred to our institution for further management. His past medical history was significant for early-stage chronic lymphocytic leukemia (CLL), which has been monitored but never treated, diabetes, gout, and atrial fibrillation.