If Pirates Want to Return to the Postseason, This Has to Change
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PITTSBURGH — The Pittsburgh Pirates haven't had much success in the past few decades, falling far short of where they want to be.
The Pirates have won five World Series, but none since 1979, marking the last time they won a postseason series.
Pittsburgh has had just six postseason appearances since then, two three-year stints in 1990-92 and 2013-15.
The Pirates also have just five winning seasons in the past 34 years, which also included a record 20 consecutive losing seasons from 1993 to 2012
While losing has been the norm for the Pirates, they had a winning season in 2026, and if they make a few changes, personnel and organizational, they could finally build a winning culture.
Pirates Must Not Show Fear in 2027
The Pirates have struggled for years for a variety of reasons, but fear is one big issue for this franchise.
Fear manifests itself in many ways, especially when it comes to a ball club.
It results in less decisive decisions, a lack of needed change, falling behind on trends and missing out on opportunities to make a team better.
The Pirates have operated, both on and off the field, with a sense of fear. Far too worried about making the wrong decision, then going for it and living with the consequences of it.
Front office decisions that stem from this fear result in a lack of ambition when desperately needed and wasted years to get better, which are crucial for a small-market team.
The Pirates not making serious offseason additions going into the 2025 offseason resulted in a 71-91 record, the dismissal of manager Derek Shelton and the wasting of Paul Skenes' Cy Young campaign.
Was this lack of roster additions that offseason due to fear? Maybe. Maybe not. But the Pirates' front office did not show the ambition and desire needed to make 2025 a successful year.
Figuratively throwing 2025 away meant that even strong offseason additions heading into the 2026 season, second baseman Brandon Lowe and first baseman Ryan O'Hearn, couldn't offset areas they needed to bolster, like the bullpen.
The Pirates' bullpen was poor in 2026, with some of their best arms regressing and blowing too many wins that hurt them in their quest for the postseason.
Pittsburgh showed more drive at the trade deadline, but they lost too many games they couldn't catch up to that point, which meant their 7-16 slump from late July to mid-August ruined their playoff chances.
Pirates manager Don Kelly received criticism, sometimes unfair, for that same fear, especially with bullpen decisions.
One game that stands out in particular is the game against the Chicago Cubs at Wrigley Field on Sept. 12, when left-handed relief pitcher Gregory Soto was spiraling in the eighth inning and Kelly didn't take him out, resulting in two runs scored, blowing the lead and the game, 4-3.
The players themselves must bear some responsibility for this as well, as when the Pirates got close to really making their postseason contention serious at the end of July, they completely failed to take advantage.
How Can the Pirates Fix This?
It's a collective issue for the Pirates, but one that takes time to correct, especially more than one season.
The Pirates made many strides in 2026, and a winning season is still a big deal, despite other small-market teams reaching the postseason far more consistently over the last decade or two.
Pittsburgh brings back most of its squad from last season, all of whom have the experience of being in a postseason race and what it requires of them.
It features a strong, young rotation, a lineup that can drive runs consistently, and an improved bullpen from last year.
Kelly also gains a year of knowing what he needs to do in those tough situations, while also having a better understanding of lineup/rotation/bullpen management.
The Pirates' front office, led by general manager Ben Cherington, made some good moves last offseason and at the trade deadline, which they must continue this offseason.
Pittsburgh has a strong group of players, a manager who desperately wants to bring winning baseball to his hometown and a front office that knows they must deliver that.
This combination could result in the first playoff appearance for the Pirates since 2015, but they must shed the fear and failure of previous teams.
2027 could be special for the Pirates and there should be nothing stopping them from going right after all their goals.
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Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.