The Pirates spent August looking like a team headed for another familiar letdown. Their offense disappeared, they dropped six straight series, and by Aug. 28 they were six games under .500. After an All-Star break that had them squarely in the National League Wild Card mix, Pittsburgh suddenly looked like it was slipping out of reach of its own preseason talk about the playoffs.
Then September flipped the script.
Pittsburgh worked its way back to .500, rattled off five straight series wins during one stretch and pushed itself back to the edge of the Wild Card race. The postseason odds were still tiny after all the damage from August, but the late surge did show something real: when the young core is healthy and producing, this roster can look a lot different.
That matters for Ben Cherington. The Pirates’ general manager is under contract through 2027, and this finish gives ownership a straightforward reason to stick with the current setup rather than start over in the front office during what already figures to be a messy offseason.
But that kind of continuity should not come with a pass.
If anything, the way the Pirates finished 2026 should put Cherington under a brighter spotlight heading into 2027, not a softer one.
The pieces are there. Paul Skenes is already one of the sport’s top starting pitchers.
Bubba Chandler, Braxton Ashcraft and Jared Jones have all started to look like potential frontline arms. Konnor Griffin, Oneil Cruz and Esmerlyn Valdez give the lineup real offensive building blocks.
And players like Ryan O’Hearn have shown how much a steady veteran bat can change the feel of this offense.
That’s the point now: the foundation is no longer just an idea.
So Cherington’s job this winter is to build on it aggressively. The Pirates still have obvious holes, still need more dependable offense around their young hitters and still cannot afford to go into another season banking on everything breaking perfectly. The August collapse was the warning sign - when injuries hit or several bats go cold at the same time, the margin gets razor thin in a hurry.
In Other News...
Pirates Own Up To A Costly Mistake Fans Wont Forget
A quiet but damaging moment in the Pirates game against the Brewers came on the bases, where a chance to add to the board vanished because of a routing mistake involving Nick Gonzales and Ryan OHearn. Third base coach Tony Beasley later took responsibility, saying he did not see the ball clearly and told Gonzales to hold at third, turning what should have been a live scoring opportunity into an avoidable pause in the action.
For a Pirates club that has spent plenty of time searching for clean execution, these are the kinds of plays that linger because they are so fixable. Gonzales said he simply followed the instruction he was given, which puts the focus squarely on the coaching box and leaves the larger question hanging around a team that cannot afford to give away chances like that, especially in a tight game against Milwaukee. [Read more 🡒]
Pirates Had No Margin For Error Against Milwaukee After One Costly Mistake
Jacob Misiorowski kept the Pirates off balance for five scoreless innings, and the margin for Pittsburgh never really got any wider after that. Milwaukees starter lowered his season ERA to 1.89 and picked up his 15th win of the year, while the Pirates scratched out just five hits and spent most of the night trying to recover from a game that slipped further away in the fourth inning.
Pittsburgh finally got on the board in the eighth, but by then the damage was done. A baserunning error earlier in the game helped stall any early momentum, and against a Brewers club that kept adding pressure, the Pirates were left with too little room to work with in a 5-1 loss. [Read more 🡒]
Pirates Face A Real Brandon Lowe Test They Usually Avoid
Brandon Lowe has given the Pirates exactly the kind of midseason jolt they hoped for when they brought him in through last offseasons three-team trade. He has been one of the most productive hitters on the roster, piling up 30 home runs and carrying an .803 OPS while giving Pittsburgh a proven presence in the middle of the lineup.
Now the question is what comes after the season, because Lowe is headed for free agency and the Pirates may have to decide whether to extend a qualifying offer. Even if they do, he is widely expected to pass on it, and the bigger issue may be whether the sides can bridge a gap in contract philosophy, with Lowe reportedly looking for a multi-year deal while Pittsburgh usually prefers shorter commitments. [Read more 🡒]