Chandler Simpson's elite sprint speed and baserunning have driven his near-certain position as the 2026 MLB postseason stolen base leader, with five steals across Rays playoff games already creating a substantial edge. The Tampa Bay outfielder led the AL with 46 regular-season steals and has extended that form into the playoffs, including multi-game streaks that have outpaced teammates like Taylor Walls and contenders such as Brice Turang or Jackson Chourio. His deep postseason run with the Rays provides additional opportunities in the World Series. A late injury, series sweep limiting at-bats, or an uncharacteristic caught-stealing surge could allow another speed threat to close the gap in remaining games.