Re-expansion pulmonary edema (RPE) after chest drain insertion is rare. The objective of this clinical case report is to highlight the importance of this chest drain insertion complication. A 35-year-old man presented to the emergency department with a chief complaint of shortness of breath and pleuritic chest pain. Further physical examination and radiographic investigations showed a left-sided hemipneumothorax. A chest drain was inserted, but subsequently the patient developed worsening shortness of breath, desaturation, and coughed out pink frothy sputum. Repeated chest radiographic and computed tomographic thorax findings suggested RPE. A nonrebreathable mask with high-flow oxygen was given to the patient to maintain his oxygen saturation. The patient was referred to the cardiothoracic team and was admitted to the hospital. Despite conservative management in the ward, the patient underwent lung decortication. Postdecortication, the left-sided lung re-expanded well, and the patient was discharged home. This case highlighted this rare, potentially fatal complication of chest drain insertion for spontaneous pneumothorax.