The Pittsburgh Pirates are entering year seven of the Ben Cherington era, where they have failed to put up a single winning season or finish above 4th in a generally very weak NL Central. Before signing Ryan O’Hearn back in December, this front office had failed to sign a single free agent to a multi-year deal, and the biggest move they made was to sign Aroldis Chapman to a one-year deal in 2024. Even for notoriously cheap and apathetic owners like Bob Nutting, this kind of performance is becoming increasingly intolerable, and it is clear that if the Pirates do not find some sort of sustained success in 2026, then the writing is on the wall for another rebuild. This type of urgency was shown with the Pirates’ offseason moves, indicating that even Ben knows that time is growing short. As we wait in anticipation for the first pitch from Citi Field, there are many things to be excited for, but also many question marks that must be solved if we are to experience Buctober for the first time in 11 years.
The Pirates Cannot Tank (Literally)
The Pirates have been in the business of playing things safe and playing for those sweet top 10 picks in the draft. Cherington has made most of his popular moves in the MLB Draft (primarily the drafting of Paul Skenes and Konnor Griffin). However, it is clear that one reason that they stopped this loser behavior is because of how the MLB Draft Lottery works. The Pirates have spent so many years picking in the top 10 that they will be barred from the best picks no matter how badly they do this season. Throwing away another year to pick 12th is a pill even Ben refuses to swallow.
There is another clock that is ticking away for Cherington, and that belongs to the 2025 Cy Young winner Paul Skenes. The Pirates have four years left of control with the best pitcher in the sport, and since they have missed the boat on extending him, that is most likely three so they can try and recuperate their losses in a potential trade. The Pirates already experienced what it is like to punt a full season of a generational talent taking the hill 33 times a season, and Ben cannot afford to do this again. This is why I have optimism that for once the Pirates will act with urgency during the season. Griffin should be up very soon; they should cut bait on players holding them back and overall have a general lack of concern for service time manipulation. It does Cherington no good to guarantee Griffin’s 2032 season if he is fired six years earlier.
We Have Actual Bats! (For Once)
There have been few things worse in my life than dedicating a non-insignificant amount of time to watching the 2025 Pirates attempt to play offense. Spencer Horwitz being the best offensive player while not even eclipsing 15 home runs made me want to claw my eyes out. Cherington understood that if he didn’t fix this he would be shown the door as he wasted another year of a fantastic pitching staff. Bringing in O’Hearn, Marcell Ozuna, Brandon Lowe, Jake Mangum, and Jhostynxon Garcia should provide a lot of depth and protection to guys like Bryan Reynolds and Oneil Cruz. It is far from an elite lineup, but it has the potential to be league average which is miles better than anything we have seen since 2020. The pitching will be good, I have almost no doubts about that—there is too much talent in the rotation to not be one of the best in the league. If the offense is even close to league average, this is a team that can make some noise come the end of September. The big thing is staying healthy, because if the Pirates are able to get 130+ games of healthy baseball out of the players listed above and their rotation, it should be a really fun season. However, this is the Pirates. Nothing goes according to plan, and there are a ton of unanswered questions about this current squad of players.
The Question Marks
I think it is quite clear that the Pirates had to resort to quite a few plan B options in their offseason. They cast their harpoons on some of the big whales like Kyle Schwarber, Framber Valdez, and Isaac Paredes and missed the mark on all of them. You can really feel this when looking over the opening day roster because there are simply some glaring holes that this team desperately needs to fill. Catcher, third base, and shortstop are all major issues for the Pirates going into this season for a multitude of reasons. Jared Triolo, a useful utility player and lefty masher, is being thrust into an everyday role at SS until Griffin comes up and will move to third. He is going to be a great defensive asset, but that bat cannot play on a daily basis.
Third is going to be manned by a tandem of Nick Gonzales and Nick Yorke, neither of whom are particularly good at defense, and both have struggled mightily hitting-wise in the majors. Catcher is a sinkhole of offense outside of Joey Bart‘s limited at-bats against left-handed pitching. The Pirates also had to sacrifice defense to make this roster much better offensively. It was kind of clear that Marcell Ozuna was never in the original plans after signing O’Hearn, but the Pirates are taking a gamble on offense and power over defense. It’s a smart gamble, as being one of the best teams in baseball according to DRS did absolutely nothing for them. However, a defense that features Lowe at 2nd, Gonzales at 3rd, and a shaky outfield of Reynolds, Cruz, and O’Hearn could lead to some infuriating losses due to poor defense.
Conclusion
While this was a successful offseason looking at the left side of the infield as it stands going into opening day ruins a lot of my positive vibes. The team is substantially improved from 2025 but it definitely feels like they’re one piece away from being a truly special unit. Seeing 6-7 competent hitters in the lineup does make my heart flutter, but there are enough holes and defensive ineptitude that some untimely injuries could unfortunately tank this season quickly.
Overall, I think this is an 84-win team, and a 13-win improvement is nothing to scoff at. The real question is whether or not this team being slightly above .500 is enough to sneak into the playoffs as a third wild card. If the Pirates don’t rise to the occasion, I do not see a future where this front office gets to continue in this job. We have been suffering for too long to deserve another year of bad baseball.
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