For the last ten seasons, the Pittsburgh Pirates have been a laughing stock in Major League Baseball when it comes to reaching the postseason. Pittsburgh has been a notoriously “cheap” franchise when it comes to its approach toward free agency. So why then did we tantalize with the title of this article, making the claim that Pirates will set sail for October? Let us chart the course to the treasures of October baseball. (And if you love Pirates content, check out our friends at Bucco Bantr. They make great Buccos content.)

FROM SHIPWRECK TO TREASURE FINDERS

Prior to this past offseason of 2025-2026, the Buccos have not handed out a multi-year deal since Ivan Nova back in 2016. Ten years to the offseason before Pittsburgh signed another multi-year deal. However, this offseason, there was a difference in the air in the Steel City. This offseason, beyond just signing Ryan O’Hearn to a multi-year deal, the Pirates seemed to be aggressive this offseason in their efforts to improve the ballclub. No longer was it just resigning Pirates legend, Andrew McCutchen, and calling the offseason complete. That being said, it is going to take more than a couple of offseason acquisitions to turn Pittsburgh into a postseason team. Pittsburgh seems to have resolved this offseason that the 2026 season was going to be different. The Pirates struggled with their power output over the past several seasons and made moves to address those concerns. The aforementioned signing of O’Hearn went along with the signing of Marcell Ozuna and the trade for Brandon Lowe. The Buccos addressed some much-needed areas of weakness, and that bodes well for the 2026 campaign.

TREASURE THAT ISN’T BURIED

There’s little question that the strength of the Pirates’ 2026 campaign will rest on the broad, hard-throwing shoulders of their ace, Paul Skenes. Skenes, the reigning defending undisputed National League Cy Young Award winner, is a monster to behold on the mound. However, for Pittsburgh, it isn’t a rotation of one. Skenes is joined by Mitch Keller, Carmen Mlodzinski, Braxton Ashcraft, and Bubba Chandler. Even though most casual non-Pirates fans may not recognize any names other than Skenes and maybe Keller, there is real talent in the Buccos staff. Pitching has always been such a pivotal focus for success in baseball. A good starting pitcher can help teams stop losing streaks, extend winning ones, and keep their teams in games even when they don’t have their best “stuff”. Plus, with the heavy emphasis in today’s game on hard-throwing bullpen arms, they are the treasured jewels of every organization. And for Pittsburgh, they seem to understand what they have on their current pitching staff and don’t want to fully see this window pass them by.

PRIZED PLUNDER

Prospects in Major League Baseball are the equivalent of a pirate’s “commandeared” treasures. And there is no bigger “treasure” by baseball standards than Konnor Griffin. Earlier this week, Nicoletta Alcamo put together a piece on Konnor and his impact on the Pirates’ franchise. (Konnor Griffin: The Face of a New Era in Pittsburgh and What It Means for the Franchise. If you haven’t read the piece, it’s definitely worth checking out.) So, we won’t spend too much time diving into what Griffin can mean for the Buccos. However, we will say that his ascension through the organization and call-up for the first home series of the 2026 season in Pittsburgh felt like baseball theater. Not to mention the fact that Pirates’ owner, Bob Nutting, FINALLY put his money where his mouth is and gave Konnor a massive extension. Konnor signed a nine-year, $140 million deal with the Pirates. This signing is massive for a small-market team like Pittsburgh. Yet, it goes beyond what it can mean for the young man playing shortstop every day for the Pirates. It’s what this signing signals and represents for fans of the Pirates as well.