For the Pittsburgh Pirates, the wait goes on. With the team officially eliminated from playoff contention in 2025, the franchise now stares at a full decade without October baseball. For fans, that absence is measured not only in years, but in memories that have grown fonder — and perhaps more painful — with time.

“Rebuild” now old enough to drive, still can’t reach October // Sean McQuillan, Staff Writer

The last taste of postseason baseball came in 2015, a season that still resonates in the minds of many Pittsburgh faithful. That team was something special — 98 wins, a rotation led by a young Gerrit Cole and an offense that looked ready to compete with the National League’s best. Cole finished in the top five in Cy Young voting, the Pirates carried themselves like contenders, and optimism buzzed through the city. 

Sure, the Pirates found themselves a new Cole — perhaps a better one — in Paul Skenes. But is it enough? Unfortunately, I have bad news for Pirates fans — that streak will continue in 2026.
Pirates GM Ben Cherington is under the impression that he will return next season, and that essentially tells us about next year’s outcome.
He is cheap. He is soft. He does not make moves. He is a very incompetent general manager who is not fit for this team’s success.
Before last Saturday’s game, Cherington had said, “It’s been really tough. I think that we have to win more games.”
Well, it is tough to win more games when you DO NOT SPEND MONEY! The last time the Pirates signed a free agent to a multi-year contract was back in December of 2016, when Iván Nova inked a $26 million deal. That deal? Consisted of a 3.99 ERA and a .500 record. Since then, the Pirates have agreed to countless one-year deals.
You can propose the “young Buccos” debate all you want, but I know this organization too well. I have cheered for the Pirates since 2011, and I am not delusional about this team and where they are heading. Skenes, Griffin, Chandler, Jones, Gonzales, Cruz — you can give me any name, and that will not move my thinking, and my knowing, that the Pirates are not just one pitcher or one big bat away. 

They are simply a general manager away, and until that changes, the Buccos will enjoy the bottom of the NL Central.

The Pirates, at long last, are ready for October // Ari Meyer, Senior Staff Writer
The Pittsburgh Pirates will make the playoffs in 2026. I know how crazy that sounds. The team that holds the second-longest active playoff drought in Major League Baseball seems quite unlikely to end that streak any time soon. Yet, I am confident that it will happen in 2026. The Pirates are set to boast one of the best pitching staffs the league has ever seen. 

With Paul Skenes, Bubba Chandler, Mitch Keller and possibly Jared Jones, the Pirates should have little trouble with their starting pitching. And they could dominate even more pitching-wise if their relievers develop as planned, or if pitchers like Braxton Ashcraft and Thomas Harrington convert to elite relief options for the team. 

The issue obviously relates to the hitting, as the Pirates really have not had an elite hitting team since the 2015 team that made the playoffs. My belief that the Pirates will make the playoffs relies on two facets when it comes to hitting. 

First, they must rely on the development of hitters in their system. That includes recent first-round selection and top prospect infielder Konnor Griffin, who will likely play shortstop. If Griffin can make the opening day roster or join the team soon after, he seems ready to make a quick impact on the team. 

Second, they must spend some money. While that will give some grief to the ownership, the Pirates must spend to compete. 

But if they can “hit” on two or three cheap deals for veteran hitters, the team can very quickly become a competitive team. With the NL Central in constant flux in terms of which teams are strong, the Pirates could take advantage of the coming season and find themselves in the 2026 MLB playoffs.