AbstractEach year, the NCAA Division I Men’s Basketball Tournament attracts popular attention, including bracket challenges where fans seek to pick the winners of the tournament’s games. However, the quantity and unpredictable nature of games suggest a single bracket will likely select some winning teams incorrectly even if created with insightful and sophisticated methods. Hence, rather than focusing on creating a single bracket to perform well, a challenge participant may wish to create a pool of brackets that likely contains at least one high-scoring bracket. This paper proposes a power model to estimate tournament outcome probabilities based on past tournament data. Bracket pools are generated for the 2013–2019 tournaments using six generators, five using the power model and one using the Bradley-Terry model. The generated brackets are assessed by the ESPN scoring system and compared to those produced by a traditional pick favorite approach as well as the highest scoring brackets in the ESPN Tournament Challenge for each year.