North Shore Nine

The latest North Shore Nine LIVE episode dove headfirst into a question that’s been simmering in Pittsburgh all summer: will Ben Cherington remain the Pirates’ general manager in 2026? What began as a lighthearted chat—complete with talk of flash mobs and Thursday Night Football bets—quickly turned into a sharp, hour-long examination of the franchise’s direction and the man steering it.

Hosts Anthony DiNardo and Tyler wasted no time outlining their frustrations. Now six years into Cherington’s tenure, the Pirates sit nineteen games under .500 despite boasting a top-five starting rotation and the league’s most electric young arm in Paul Skenes. The offense remains one of MLB’s worst, and nearly every major transaction of the past 18 months—from offseason signings to the David Bednar trade—has either fizzled or backfired. Rival executives even told ESPN that owner Bob Nutting might be “too cheap to fire Ben,” adding another layer to the uncertainty.

The show also spotlighted manager Don Kelly, who’s steadied the dugout but hasn’t sparked enough offensive improvement to change the team’s trajectory. With ONeil Cruz struggling, payroll constraints looming, and a potential Mitch Keller trade as the only clear path to adding bats, the hosts agreed that 2026 feels like a make-or-break year—one that could define the Skenes era and the club’s future.

Despite a bleak assessment, there’s hope in the farm system, highlighted by rising star Konnor Griffin and an intriguing group heading to the Arizona Fall League. But until the front office proves it can build a complete roster, Pirates fans remain stuck between patience and exasperation.