A 2-year-old child presented with an airplane game piece from the board game Monopoly lodged in her esophagus. The airplane’s wings, engines, and winglets acted like fish hooks that entered the esophageal mucosa easily but were difficult to extract. Chest radiographs were used to estimate the airplane wingspan dimensions, and a Foley catheter was used to dilate the esophagus to allow foreign body extraction via rigid esophagoscopy with optical forceps. Deliberate deep placement of the endotracheal tube facilitated surgical manipulation. This case report highlights the importance of teamwork, communication, and the involvement of multiple disciplines, each with their unique experience and expertise, to formulate a plan of action for patients during unique surgical emergencies.