Managers of perennially dominant teams rarely win Manager of the Year. In practice, the award functions less as a reward for the best overall record and more as a "Most Improved Team" honor—recognizing the skipper whose squad most drastically outperformed expectations.

Historically, Box-Toppers simply picked the manager of the team that finished with the most Box-Toppers points in each league. For 2026, those choices were Aaron Boone of the Yankees (120.1) and Dave Roberts of the Dodgers (142.7).