A 44-year-old male with a history of well-controlled human immunodeficiency virus disease and Crohn's disease presented with fever, cough, and left-sided chest pain with radiation to his back. His medical history was notable for a medically managed spontaneous microperforation of the colon at the splenic flexure 30 months prior, and recurrent left-lower-lobe pneumonia with empyema and a splenic abscess within the past 24 months. CT demonstrated a complex left pleural fluid collection with fistulous connection through the spleen and into the large bowel. The patient tolerated a diverting loop ileostomy without complications and was discharged home with plans for resection of the fistulous tract and splenectomy in several months.