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Chemoradiotherapy (CRT) is commonly employed in the management of esophageal carcinoma-either definitively or as part of a trimodality strategy with includes surgical resection. For patients treated with trimodality therapy, the most optimal sequence of chemoradiation (CRT) in relation to surgical resection is unclear. We reviewed the efficacy, advantages, and disadvantages of preoperative CRT versus postoperative CRT in esophageal cancer patients treated with trimodality therapy. Preoperative chemoradiation enables early treatment of distant metastases while simultaneously treating the primary disease, facilitates definition of radiotherapy target volumes, and may allow resection of advanced disease. It does, however, have considerable toxicity and may reduce the ability of some patients to tolerate resection. Postoperative CRT allows for early debulking, rapidly addresses dysphagia, and allows for CRT based on accurate pathologic staging, but delays systemic treatment. Randomized studies that compare preoperative with postoperative CRT in treating esophageal cancer are needed to identify conclusively the best standard of care. Based on the study information currently available, we conclude that treatment options should be tailored to the individual patient.