Chandler Simpson enters the 2026 World Series as the clear favorite for postseason stolen-base leader, reflecting his American League-leading 46 regular-season steals, elite speed profile, and Tampa Bay's extended playoff run that provides additional opportunities. Jackson Chourio and David Hamilton trail as the next most likely outcomes, buoyed by Milwaukee's deep postseason path and their own base-stealing ability, though both trail Simpson in volume and consistency. The tight clustering among top contenders stems from the small sample of postseason games, variable lineup spots, and matchup-dependent aggression on the bases, leaving room for late surges by speed threats like Brice Turang or Jazz Chisholm Jr. if their teams advance further or if volume increases in a longer series.