Ben Cherington Year Eight? Pirates Face a Massive Decision.

Is Ben Cherington really coming back for Year 8?

Reports from Buster Olney and Jason Mackey suggest the Pirates could retain Cherington for 2027, despite seven seasons without a winning record or postseason appearance. DiNardo, Jim and Tyler debate what progress in 2026 actually means, whether Cherington has done enough to warrant another season, and how much the final nine games should matter.

Plus, does finishing .500 mean anything at this point? And the crew looks ahead to the Pirates prospects headed to the Arizona Fall League, including Wyatt Sanford and Easton Carmichael.

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