CHERINGTON'S CHALLENGE: Can the Pirates’ GM FINALLY Push Pittsburgh Over the PLAYOFF EDGE?

Pittsburgh Pirates eye October after Ben Cherington’s winning foundation—can they turn 82 into a playoff berth? Gary Morgan breaks down the Pirates’ first winning season under Cherington, examining his successes with prospects like Konnor Griffin and Rafael Flores Jr., key trades, and the rising young core that fueled the team’s 82-80 finish. With a +28 run differential, this is no fluke—yet questions linger on whether low-budget moves and past misses still limit upside. Morgan evaluates critical issues for the offseason: Flores’ development as primary catcher versus Nick Gonzalez’s challenges at third base, the leadership roles of veterans Brandon Lowe and Ryan O’Hearn, and how defensive improvement might further close the gap in the NL Central. The conversation explores what it’ll take for the Pirates to bridge the final wins to October, plus predictions for MLB’s unconventional playoff field. Will Cherington finally deliver postseason baseball to Pittsburgh?