The Pirates appear to be heading toward one of their biggest offseason decisions: whether Ben Cherington returns for an eighth season as general manager. DiNardo, Jim and Tyler debate whether the progress made in 2026 outweighs seven seasons without a winning record or playoff appearance. They also discuss whether finishing .500 matters, what another Cherington offseason could look like, and prospects Wyatt Sanford and Easton Carmichael heading to the Arizona Fall League.