The Pirates can say all the right things, but the standings told the real story.
Pittsburgh was officially knocked out of postseason contention this past weekend with eight games left in the 2026 season, closing the door on a year that was supposed to end with the club playing for more. That goal was clear after the 2025 season, and it still went unmet.
There was progress, sure. This wasn’t the same team that stumbled through the worst record in baseball in 2020 or the back-to-back 100-loss seasons that followed in 2021 and 2022.
The Pirates were better in 2023 and 2024, even if both seasons finished the same way, with 76-86 records after strong starts and late collapses. But better isn’t the same as good enough, and not nearly enough to end an 11-year postseason drought that now stands as the second-longest in MLB, behind only the Los Angeles Angels’ 12-season run since 2014.
That drought has come on the watch of general manager Ben Cherington and team president Travis Williams, who took over after the 2019 season. Since then, Pittsburgh has gone 426-570 (.428), the fifth-worst record in baseball, with no winning seasons and no playoff appearances to show for it.
The long rebuild brought major changes. The Pirates moved on from veterans such as pitcher Joe Musgrove and outfielder Starling Marte, trading away much of their core in the hope that prospects would eventually carry the franchise forward.
The payoff took time to arrive, and in some cases it never really did. The turnaround didn’t begin until draft picks started developing and reaching the majors.
Even then, the front office didn’t push hard enough when the window started to crack open. After 2024, with Paul Skenes and Jared Jones debuting and Bryan Reynolds and Oneil Cruz ready to compete, Pittsburgh had a chance to build around that young core.
Instead, the 2025 offseason brought only modest additions: Tommy Pham, Adam Frazier and a reunion with 38-year-old Andrew McCutchen. The result was predictable.
Derek Shelton was fired after a 12-26 start, and the Pirates finished 71-91, fifth-worst in baseball.
This past offseason finally brought moves that changed the lineup. Ryan O'Hearn and Brandon Lowe were added, and both were described as incredible additions that transformed the offense.
But even those moves couldn’t cover everything else. The Pirates lost too much offense to injury, the rotation lacked depth, and the bullpen was a problem until it was addressed at the trade deadline.
That’s the part Pittsburgh can’t ignore. A postseason team is built over years, not by one or two splashes. The Pirates have to keep adding, keep subtracting when needed, and keep reinforcing the roster around the young core they already have.
Cherington owned the disappointment on The Pirates Insider Show on 93.7 The Fan ahead of the series finale against the Kansas City Royals at PNC Park on Sept. 20. He also said the club is in a better place than it was a year ago and vowed the Pirates will "double down" to make sure they reach the postseason next year.
That’s the right message. Accountability matters.
But the frustration won’t disappear just because the front office says the right things. The injuries, the bullpen issues and the missed opportunities all added up to another season without meaningful baseball in Pittsburgh.
The next step is obvious: strengthen the bullpen, add depth to the starting staff and the position-player group, and keep the best pieces in place, including soon-to-be free agent Lowe. The Pirates have a young core worth building around. Now they have to actually build around it.
In Other News...
Ben Cherington Just Framed The Pirates' Biggest 2027 Question
Ben Cherington used his latest turn on the Pirates Insider Show to put a broader lens on where Pittsburgh stands after 2026. He acknowledged the club made progress but still came up short of the postseason, pointing to a better run differential, stronger bullpen work after midseason changes, and the impact of several young players as signs the organization was moving in the right direction.
The bigger point, though, was the one he kept steering toward: progress only matters if it carries into 2027. Cherington stressed accountability and the need for the Pirates to keep improving, which leaves the franchise facing the same familiar test this winter and beyond - turning encouraging steps into a season that lasts deep enough to matter. [Read more 🡒]
Pirates Face A Defining 2027 Test With Their Lineup-Changing Slugger
The Pirates 2027 planning already has a clear focal point, and it starts with Brandon Lowe. Pittsburgh watched its postseason hopes disappear in 2026 when the Padres beat the Marlins, but even with the year over, the front office is now staring at a more immediate question: how hard should it push to keep the lineups top power threat? Lowe has been the kind of bat that changes the shape of an order, and his looming free agency makes him one of the most important names on the roster conversation.
There is at least some reason for optimism on Pittsburghs side. Lowe has said he is open to returning, which gives the Pirates a chance to keep a proven slugger in place rather than try to replace his production from scratch. The challenge, as always for a team trying to map out its next step, is whether interest and fit turn into a deal before another team gets involved. [Read more 🡒]
Pirates Face An Uncomfortable Luke Weaver Question After Rough Debut
Luke Weavers first stretch with the Pirates brought a jarring contrast to what he had been giving the Mets, and it left Pittsburgh with a familiar bullpen dilemma. The right-hander arrived as part of a trade and was asked to help stabilize the relief mix, but his run prevention quickly climbed in a way that made the move look far less tidy than it did on paper.
The sample is still small at 14 appearances, and some of the underlying indicators point to a rough break of the ball rather than a complete collapse in ability. Weaver also had a severe bout with poison ivy in mid-August, adding another layer to a difficult finish, yet the Pirates still appear set to lean on him as a key bullpen piece next season while they try to sort out what was noise and what was real. [Read more 🡒]