Background: Patients with body mass index (BMI) >= 50 have more obesity-associated medical problems and often require more aggressive surgical management. Few single-institution comparative studies have been published examining this specific population. Objectives: The study aims to compare the weight loss and diabetes remission effects of sleeve gastrectomy (SG), Roux-en-Y gastric bypass (RYGB), and biliopancreatic diversion with duodenal switch (BPD/DS). Setting: Rural academic tertiary care center. Methods: We conducted a retrospective cohort study using prospectively collected data. All patients with a BMI >= 50 who underwent an SG, RYGB, and BPD/DS were included. Comparative analysis was performed for complications, readmission rates, weight loss, and diabetes remission. Results: Excess weight loss at 3 years was 40.1% for SG, 54.1% for RYGB, and 67.4% for BPD/DS, with BPD/DS performing significantly better (P <.001). Complete diabetes remission at 5 years was 29% for SG, 61% for RYGB, and 79% for BPD/DS. BPD/DS had significantly longer operative times (P < .001) and rates of minor complications (P 5 .02). Conclusions: BPD/DS achieved superior sustained weight loss and diabetes remission compared with RYGB and SG. (Surg Obes Relat Dis 2025;21:548-553.) (c) 2025 American Society for Metabolic and Bariatric Surgery. Published by Elsevier Inc. All rights are reserved, including those for text and data mining, AI training, and similar technologies.