For much of Ben Cherington’s time with the Pittsburgh Pirates, the idea of extending his contract might have seemed like a joke to many fans. The long rebuild, the endless debates over payroll, and a major league roster that often felt lacking all contributed to a sense of frustration. Even as the farm system began to churn out promising talent, Pirates fans had every right to call for urgency and accountability, yearning for a team that truly looked like it was aiming to win.
But now, the Pirates might be creeping toward a decision regarding Cherington that few anticipated. According to Ken Rosenthal, Cherington is locked in through 2027, and given the Pirates’ current trajectory, an extension could be more than just a distant possibility. This isn’t to say Pittsburgh is now a finished product or that the front office should escape criticism, but the Pirates’ progress is becoming increasingly noticeable.
Despite a rocky start in June, with an 8-12 record following a strong May, the Pirates have shown promising signs. They entered the week with the fifth-best runs-per-game average in MLB, a rotation boasting the ninth-best ERA, and a plus-23 run differential. These stats reflect a team that's finding its stride, even while dealing with injuries to key players like Konnor Griffin and Oneil Cruz.
Cherington’s offseason moves are gaining validation as the season unfolds. The acquisitions of Ryan O’Hearn and Brandon Lowe have added much-needed depth and credibility to the lineup.
Rosenthal also pointed out that Cherington is actively seeking roster upgrades, particularly in the bullpen, and is open to discussing prospects or even the No. 34 pick in this year's draft. This kind of proactive approach is exactly what fans have been craving from the front office for years.
Yet, skepticism remains. The Pirates must still complete the task at hand. Staying competitive is not synonymous with making the playoffs, and fans are weary of seeing moral victories presented as actual progress.
The timing of all this adds another layer of complexity. With a lockout looming after 2027 and the potential introduction of a salary floor that could significantly impact how low-revenue teams operate, stability might become more crucial than ever. If the Pirates believe Cherington is steering them toward sustainable success, they might hesitate to change leadership just as the sport’s economic environment is poised to shift.
While fans might not be thrilled with the idea, extending Cherington’s contract is suddenly not out of the realm of possibility.
In Other News...
Pirates Rumored Catcher Swing Could Test Everything Fans Fear About This Deadline
The catching market is suddenly one of the more intriguing places for the Pirates to look as the deadline approaches, and it is easy to understand why. Pittsburgh has been linked in speculation to names such as Luis Arraez and Willson Contreras while also weighing whether it should lean into its current group or try to add a more proven bat behind the plate, all against the backdrop of a payroll that leaves little room for mistakes.
Endy Rodriguez has given the club a reason to think twice about chasing a big swing, especially now that he is healthy again and Joey Bart is out of the picture. The question for the front office is whether it wants to spend real prospect capital to solve a need that might already have an internal answer, or whether the smarter play is to stay patient and shop on the margins instead of forcing a move that could cost too much future value. [Read more 🡒]
Ben Cherington's Bullpen Comments Won't Calm Frustrated Pirates Fans
The Pirates bullpen has been one of the early-season sore spots dragging down a club that still wants to think it can stay in the playoff chase, and Ben Cherington did nothing to pretend otherwise during an appearance on The Pirates Insider Show. The general manager acknowledged the relief corps needs help, which at least matched what frustrated fans have been watching unfold, and he pointed to the teams one bullpen-related move so far, the trade that brought Hunter Stratton in from the Braves for catcher Joey Bart.
Cheringtons comments, though, also made clear that any larger fix is not going to arrive right away. He said bullpen trades are likely, but they may not come until after the July draft, pushing the meaningful reshaping of the relief mix closer to the trade deadline than to the present moment. For a fan base already anxious about how much damage the bullpen has done, that timetable is probably the least reassuring part of all. [Read more 🡒]
Pirates Injury Picture Just Took Another Frustrating Turn
Ben Cheringtons latest injury update offered one bit of progress and two reminders of how quickly the Pirates depth can get tested. Oneil Cruz is moving forward in his rehab from hand fractures, with the shortstop beginning gripping exercises and heading to Bradenton, Florida to continue the recovery process after having his cast removed. It is not a finish line, but it is at least a sign that one of Pittsburghs most important lineup pieces is turning a corner.
The rest of the picture was less encouraging. Wilber Dotel began a rehab assignment, but his recovery has already required a reassessment after he felt some discomfort, while Spencer Horwitz is facing a longer absence after suffering a left hamstring injury in late June. Horwitz had become a useful middle-order presence before getting hurt, and the Pirates now have to keep piecing together the infield and lineup while waiting for the injury count to settle down. [Read more 🡒]