Iatrogenic esophageal perforation during endoscopy in the setting of malignancy is an uncommon but often devastating complication and presents a formidable challenge to the surgeon. We sought to determine the efficacy of a self-expanding plastic stent for esophageal perforation before neoadjuvant chemoradiation in a single patient. A 74-year-old woman with a T4N0 adenocarcinoma at the gastroesophageal junction was perforated during upper endoscopy. We elected to manage the perforation with a silicone-covered, self-expanding Polyflex stent. Subsequent studies revealed good positioning of the stent with exclusion of the perforation from the esophageal lumen. The patient subsequently underwent neoadjuvant chemoradiation therapy with cisplatin, 5-flourouracil, and external beam radiation (2640 Gy) followed by minimally invasive, hand-assisted transhiatal esophagogastrectomy. We describe the first case of endoscopic stenting for locally advanced, perforated esophageal cancer for the purposes of administering neoadjuvant chemoradiation as a bridge to definitive surgery. This patient was able to resume oral nutrition after stenting and during neoadjuvant therapy, experiencing no major complications from chemoradiation. Chemoradiation does not necessarily preclude the use of endoscopically placed covered plastic esophageal stents as a bridge to resection, even in the face of iatrogenic perforation.