WARNING: Ben Cherington and Pittsburgh Pirates FAIL to Address Crucial Pitching DEPTH – Who’s to Blame?

Pittsburgh Pirates' postseason hopes falter as pitching depth concerns prove prophetic. Could a proactive offseason have changed the outcome? Gary Morgan unpacks how the Pirates' lack of starting pitching—despite warnings all winter—ultimately led to September struggles. He spotlights workloads for Braxton Ashcraft, Bubba Chandler, Jared Jones, and Mitch Keller, questioning front office decisions and the reliance on best-case scenarios. The conversation shifts to Don Kelly’s management, dissecting bullpen choices, lineup dynamics, and the real impact a manager can have on MLB wins. Key topics include prioritizing Brandon Lowe’s contract, Oneil Cruz’s extension, CBA implications, and whether ownership will finally fill roster holes before the season. Will the Pittsburgh Pirates learn from these costly missteps and make the aggressive moves needed to contend in 2027?