What happened: Former manager Joe Maddon addressed the Chicago Cubs' 2016 championship run, his departure from managing, and the evolution of dugout leadership in an interview with Jon Heyman. The discussion also addressed the New York Mets and their offseason pursuit of top rotation targets.

Why it matters: Maddon's reflections detail the broader shift toward front-office analytics that has redefined traditional managerial responsibilities across Major League Baseball. Meanwhile, New York remains positioned to aggressively pursue premium pitching upgrades ahead of the 2027 season.

What to watch: Free-agent discussions and managerial market evaluations will continue leading into the winter meetings.