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Esophagectomy remains the standard therapy for localized esophageal cancer, but postoperative function depends heavily on effective gastric conduit emptying. The aperistaltic conduit located in the negative pressure thoracic cavity is at risk of delayed gastric emptying leading to aspiration and pulmonary complications. This article summarizes historical and contemporary evidence evaluating pyloroplasty and alternative pyloric drainage strategies during esophagectomy. While earlier trials produced mixed results, recent level I evidence supports pyloroplasty as a safe adjunct that reduces gastric outlet obstruction and postoperative interventions. Meticulous conduit construction and vigilant postoperative assessment remain essential. There continues to be controversy, and an ongoing randomized trial, The PYNI-GAREREO Phase III Trial of Pyloroplasty Vs. No Pyloroplasty will be completed in the near future. (Trials.2023 Jun 19;24:412) and will add further level 1 evidence to this controversy.