Delayed emptying of the gastric conduit following esophagectomy can be associated with an increased incidence of complications including aspiration pneumonia and anastomotic leak. The aim of this systematic review is to evaluate the current modalities of pyloric drainage following esophagectomy and their impact on anastomotic integrity and postoperative morbidity. Medline, Web of Science, Cochrane library, trial registries, and conference proceedings were searched. Five pyloric management strategies following esophagectomy were evaluated: no intervention, botulinum toxin (botox) injection, finger fracture, pyloroplasty, and pyloromyotomy. Outcomes evaluated were hospital mortality, anastomotic leak, pulmonary complications, delayed gastric emptying, and the late complication of bile reflux. Twenty-five publications comprising 3172 patients were analyzed. Pooled analysis of six comparative studies published after 2000 revealed pyloric drainage to be associated with a nonsignificant trend toward a reduced incidence of anastomotic leak, pulmonary complications, and delayed gastric emptying. Overall, the current level of evidence regarding the merits of individual pyloric drainage strategies remains very poor. There is significant heterogeneity in the definitions of clinical outcomes, in particular delayed gastric emptying, which has prevented meaningful assessment and formulation of consensus regarding the management of the pylorus during esophagectomy. Pyloric drainage procedures showed a non-significant trend toward fewer anastomotic leaks, pulmonary complications, and reduced gastric stasis when employed following esophagectomy. However, the ideal technique remains unproven suggesting that further collaborative investigations are needed to determine the intervention that will maximize the potential benefits, if any, of pyloric intervention.