Ben Cherington believes the Pirates made important progress in 2026. But he also knows more will be required for a postseason return.
Speaking Sunday on the Pirates Insider Show on 93.7 The Fan, Cherington discussed feeling encouraged by some of what he's seen this season ... but also Pittsburgh missing out on the postseason and how those two things can coexist.
"If you're not playing games in October, you haven’t met what you set out to do,” Cherington said. “I think we look at this team as clearly taking a step forward ... and not a big enough one. There's more work to do.
“We are improved. I think there are legitimate things we can look at that provide evidence for that improvement. And we have to find a way to get better, because our fans, this organization deserves to be playing games in October. That’s our sole focus.”
As Cherington reflected on what has occurred this season, one topic of conversation involved the number of young, controllable players who’ve had strong showings in 2026: Konnor Griffin, Esmerlyn Valdez, Endy Rodríguez, Rafael Flores Jr., Bubba Chandler, Mason Montgomery, Braxton Ashcraft and Jared Jones.
None are older than 26. Griffin is just 20, Valdez 22.
Together, they’ve been worth 14.8 wins above replacement, per FanGraphs. That's a lot of production for a talented group of young players in their first or second full seasons.
Cherington believes it puts the Pirates in a better place heading into 2027, with those guys supplementing the core of Paul Skenes, Bryan Reynolds, Oneil Cruz and Ryan O'Hearn, and it’s on him and others to do the necessary work to patch the remaining holes and put this group over the top.
“If we start thinking about 2027, our starting point is stronger than it was at the beginning of the offseason last year,” Cherington said. “It doesn’t take away that we’re accountable for pushing this team into the postseason. That didn’t happen. We’re gonna double down and do everything we possibly can to make sure we do make that happen next year.”
The Pirates entered Sunday’s game 11-6 in September and seemingly picking up where they left off before Griffin, Cruz and O’Hearn were lost for a sizable stretch with injuries. Cherington has been pleased with the level of fight, though he believes the Pirates need to play consistently cleaner baseball in 2027.
One area of improvement — other than wins and losses — can be quantified via the Pirates’ run differential. It's jumped from -62 in 2025 to +28 entering Sunday, a 90-run swing.
Cherington believes run differential can be predictive of current and future success. Those strides can be attributed to an offense that went from last to fifth in runs (entering Sunday) and a bullpen that's been MLB's best when looking at fWAR since the All-Star break (4.8).
It also doesn't truly matter until the record changes.
"Nobody's gonna jump up and down and pat ourselves on the back about improved run differential," Cherington said. "The only reason it matters is because it’s a pretty important sign that the roster has improved.
"Now we have to make sure it keeps improving and be dogged about improving the areas that are still not as strong as others."
Speaking of the bullpen, that group obviously struggled before wholesale changes were made around the MLB Trade Deadline.
The bullpen reboot has worked, but should the Pirates have acted sooner? Cherington admitted (unprompted) he’s been asking himself that question.
“If we look back … and certainly I’ve asked myself and we’ve asked ourselves, ‘Is there anything we could have done sooner?’ You don’t know,” Cherington said. “If there was something obvious we could have done sooner, we would have done it.
"Ultimately we’re accountable and I’m accountable for making that work. Eventually it did improve. I do think we go into the offseason and next year with a stronger foundation in the bullpen.”
Cherington isn’t wrong. Mason Montgomery has been worth the most fWAR (1.3) since the All-Star break. Luke Weaver, Lake Bachar, Yohan Ramírez, Carmen Mlodzinski, Wilber Dotel and Evan Sisk should all return. Khristian Curtis and Antwone Kelly have shown promise, as well.
“We’re excited about those guys,” Cherington said. “We’re starting from a stronger foundation as we look to next year.”
It should be similar behind the plate. Entering Sunday, Pirates catchers were tied for fifth in home runs (27), eighth in OPS (.741), ninth in fWAR (3.4) and tied for ninth in wRC+ (101).
Henry Davis, Joey Bart, Endy Rodríguez and Rafael Flores Jr. have been productive, though Bart was traded and Rodríguez can’t seem to stay healthy.
Still, Cherington believes Davis has produced strong underlying numbers at the plate, and Flores has evolved probably more than anyone in this group.
“We believe all three can be primary catchers on a Major League team,” Cherington said of Davis, Flores and Rodríguez.
“The offensive side of Henry’s game hasn’t been at the level we anticipated it would be. It doesn’t mean it won’t get there. We see a guy who’s not striking out, who’s hitting the ball hard and generally making contact. Sometimes guys like that are only an adjustment or two away from putting up much better numbers. We all know the defensive side of his game is a strength.
“Flo has come up and really looked like a big piece of the lineup offensively. He’s done some really good things defensively, too. … We see it as a strength going forward. I just hope that group of three continues to challenge each other.”
The last answer Cherington gave involved top 100 prospects positioned to potentially help the Pirates in 2027: Seth Hernandez (MLB Pipeline No. 7), Edward Florentino (No. 32) and Murf Gray (No. 91).
Along with Wyatt Sanford, who's just outside the top 100, those guys should start at Double-A or above and aren't far away from helping the Major League club.
"It will obviously come back to those players and how well they perform, the adjustments they make and needs on the [MLB] team," Cherington said. "No guarantees. But if you have that level of talent and you start in Double-A, there’s a chance."
Jason Mackey: Jason.Mackey@pirates.com and @JMackey_PGH on X.