The Pittsburgh Pirates are heading into a stretch that will tell the story of their season, and it starts with the Chicago White Sox.
After that comes a series with the Chicago Cubs, and the way these two matchups play out could decide whether Pittsburgh keeps any real Wild Card hope alive in the National League. Drop either series, and the path gets awfully thin.
For the Pirates, that makes the three-game set against the White Sox a must-manage, must-finish, must-win kind of assignment. And if they’re going to get it done, they need a few things to break their way.
Konnor Griffin is at the top of that list. His return from a two-month absence gave Pittsburgh a lift right away, and his aggressive baserunning helped spark a Buccos win over the Los Angeles Angels in his first game back.
But the bat has been quiet since then. Griffin has gone hitless in his first 10 at-bats since returning, even though his larger body of work as a 19-year-old debuting in the MLB has been strong: a .264 batting average, five home runs and 25 runs batted in over 250+ at-bats.
The Pirates need that version of Griffin again, and they need it now. His return has already brought energy, but Pittsburgh could use his production to provide the next jolt.
Mason Montgomery has been giving them exactly the kind of relief work that can carry a team through tense September baseball. The left-hander has been dealing with serious velocity and sharp command, and over the last month and a half he’s been one of the Pirates’ best bullpen arms.
In his last 14.2 innings pitched, Montgomery has given up only seven hits. Even more telling, he hasn’t allowed a run in that stretch.
The last time he gave up a run in relief was on July 26th against the Cubs. If Pittsburgh is going to keep its late-season push alive, it needs that run of dominance to keep rolling starting with the White Sox series.
Then there’s Esmerlyn Valdez, whose midseason call-up gave the Pirates a real jolt of power before opposing pitchers started to settle in on him. September hasn’t been nearly as kind. In his last 15 at-bats to begin the month, Valdez has only one hit, and his last home run came on August 24th.
The Pirates need his power back in the mix. If they’re going to survive this stretch, they need Griffin to get hot, Montgomery to keep locking things down, and Valdez to rediscover the strength that made him such an intriguing spark in the first place.
In Other News...
Pirates Still Have Two Lineup Questions They Cannot Dodge This Winter
As the Pirates head into another crucial winter, the familiar conversation around lineup certainty is already starting to take shape. Catcher remains a major question, with Henry Davis, Endy Rodrguez and Rafael Flores Jr. all part of the mix, and second base is another spot that needs a clearer answer after the club leaned on Brandon Lowe for offense there. It is the kind of roster puzzle that can quietly define an offseason, especially for a team still trying to turn long-term ideas into dependable production.
What Pittsburgh cannot afford this time is to treat those openings like placeholders and hope the answers arrive later on their own. The organization needs a real plan at catcher and at second, not just a collection of names and a timeline built around development or recovery. The Pirates have spent enough winters talking about upside and possibility, and this one figures to test how ready they are to make firm choices instead. [Read more 🡒]
Pirates Just Lost A Young Starter At The Worst Possible Time
Braxton Ashcrafts season has ended in frustrating fashion, with the Pirates placing the right-hander on the 15-day injured list retroactive to Sept. 7 because of discomfort in his throwing arm. Manager Don Kelly said the club does not expect Ashcraft to pitch again in 2026, though the tests so far have not shown any structural damage, a small bit of relief in an otherwise unwelcome update for a team trying to piece together innings down the stretch.
The timing is especially rough for a Pirates staff already bracing for a bullpen game in the next turn through the rotation. Pittsburgh moved quickly to bring up a right-hander from Triple-A Indianapolis to fill Ashcrafts roster spot, but the larger concern is the loss of a young arm the club would have rather protected as it finished the year. A season that had already tested the Pirates pitching depth just got a little thinner. [Read more 🡒]
Pirates Rotation Pressure Just Got Worse With Braxton Ashcraft Concern
Braxton Ashcrafts rapid rise from a lower-workload role to a meaningful part of the Pirates rotation picture hit a snag this week, as the right-hander was placed on the 15-day injured list retroactive to Sept. 7 because of right arm discomfort. Early indications suggest the issue does not appear structural, but testing is still ongoing, leaving the club to wait and see how long it might be without one of its more intriguing arms.
For Pittsburgh, the timing adds another layer of strain to a rotation that already has Mitch Keller on the injured list. Ashcrafts workload had jumped significantly from the previous season, and the Pirates were trying to see how much he could handle as the year wore on. Instead, they are now juggling another pitching question at a point in the schedule where every healthy starter matters. [Read more 🡒]