The Pittsburgh Pirates were supposed to be pushing for the playoffs in 2026. That was the expectation president Travis Williams laid out after a disappointing 2025 season, and it was a major reason the team decided to keep general manager Ben Cherington rather than start over. But with Pittsburgh still sitting in the bottom half of the NL Central, that decision is now drawing the ire of the same fans who were promised a playoff push. Some of them are calling for a change of team leadership.
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“Pirates president Travis Williams should be fired as soon as this season ends,” Pirates’ loyalist pittsburghpirateguru posted on X. “Bringing back the same GM Ben Cherington and expecting different results? How did this turn out, Travis? Another losing season.”
The criticism is rooted in Williams’ own words from last year. While defending the decision to keep Cherington, the Pirates president made it clear that the team’s goal for 2026 was to reach the playoffs, calling it the expectation “period, full stop.” With Pittsburgh once again struggling to make a postseason push, those words have now come back to haunt the front office.
The fan’s post included a video of Williams speaking after the Pirates finished the 2025 season at the bottom of the division. In it, he explained why the organization believed making a change at general manager would set the team back and why it chose to stick with Cherington for another season.
“We felt at the end of the day that making a change as a general manager would set us back. That’s not what our fans expect. That’s not what we expect,” Williams said in 2025.
The Pirates finished last season with just 71 wins, and they are not far off that pace in 2026. At 67-71, Pittsburgh sits fourth in the NL Central and six games behind the final Wild Card spot with 24 games left. They are not eliminated yet, but another missed postseason would extend the franchise’s playoff drought to 11 years. It has also been nearly half a century since Pittsburgh last won the World Series, back in 1979.
That history helps explain why the frustration has reached this point. The Pirates have been waiting for a turnaround for years, and another season outside the postseason would mean another year of waiting.
Yet the numbers suggest this is not a team completely out of its depth. Pittsburgh ranks 18th in MLB with a 4.19 ERA and fifth with a .252 batting average. With 24 games still to play, one could argue that there is still time for the Pirates to make a late push, but they’ll need to win 18-20 of those games to make the playoffs safely. For many fans, the bigger concern is no longer whether the team can sneak into October this one time; it is whether the front office has done enough to build a team capable of doing it convincingly.
The Pirates do have pieces to build around. Their rotation features young stars such as Paul Skenes and Jared Jones, while the lineup has shown that it can produce runs. The bigger concern has been consistency and depth, particularly among the position players. For some fans, that points to a larger problem with the organization’s ability to develop and retain impact talent around its young stars.
That has also put the spotlight on Cherington’s approach to building the roster. Critics argue that the GM has relied too heavily on short-term fixes instead of making moves that could give Pittsburgh a long-term cornerstone. They point to both free-agent signings and trades as examples, while questioning whether Cherington has shown enough urgency to turn the Pirates into contenders.
Fans want to see the front office make bolder moves
When the X user said that Williams should be fired after the season, one fan shot back, saying, “Why wait?”
Another loyalist seemed to be even more furious with all the uncertainty and subpar performance. His comment read, “He should be fired and sued for every dime he earned while employed here. Total incompetence.”
Another user wrote, “Here’s the problem. Good organizations don’t try and win once out of every 10 yrs.”
The patience is now wearing thin for Cherington as well. Hired in November 2019 to help turn the Pirates into contenders, he is now in his seventh season as GM without a sustained postseason run to show for it. With Pittsburgh once again struggling to break through, some fans are beginning to question what exactly has changed under his leadership.
Hence, one fan asked, “Just what does he do for the club?”
Another user highlighted that it’s not just on Cherington or Williams anymore; team owner Bob Nutting should be held equally responsible for the disappointment.
“Why don’t we blame the [expletive] owner who won’t spend money. We have one of the lowest payrolls in baseball. Can’t field a competitive team like that,” read another comment.
With the season entering its final stretch, the Pittsburgh Pirates now have little time to change the narrative on the field. A late surge could still keep their playoff hopes alive, but missing October would put even more pressure on the organization to make changes this offseason. Whether that means moving on from Cherington, Williams or taking a different approach to building the roster, Pittsburgh’s front office will have to answer for another season that fell short of the expectations it set.