The use and effectiveness of video-assisted thoracoscopic surgery (VATS) for the treatment of empyema and complex parapneumonic collections in pediatric patients is well documented. Timing of this intervention still remains controversial. We reviewed our experience with VATS to determine if it should be used as the initial procedure in children with pleural collections. We reviewed all pediatric (age younger than 17 years) patients with a diagnosis of pneumonia admitted between July 1998 and June 2008. Demographics, comorbidities, laboratory data, and hospital length of stay (LOS) were evaluated. Patients were divided into groups: those who only had thoracentesis or thoracostomy (Group A), those who underwent a procedure and then required VATS (Group B), and those who went directly to VATS (Group C). We identified 382 patients admitted with pneumonia. Of these, 79 (21%) required a thoracic drainage procedure. Overall, 49 (67%) of patients with a thoracic fluid collection underwent VATS at some point. With regard to type of intervention, there was no statistical difference noted in clinical variables. Thirty (38%) patients were in Group A, 18 (22%) in Group B, and 31 (39%) in Group C. LOS for Group C (10.5 days) was significantly (P < 0.05) shorter than for both Group A (14.8 days) and Group B (15 days). Only two (6%) patients required conversion to open thoracotomy. A high percentage of children initially treated by tube thoracostomy eventually require additional interventions, leading to increased LOS. As a result of its simplicity, safety, and efficacy, VATS pleural evacuation can be recommended as the initial intervention in pediatric parapneumonic effusions and empyema in patients who do not require emergent drainage.