Pittsburgh Pirates general manager Ben Cherington talks with reporters during Major League Baseball’s general manager meetings, Wednesday, Nov. 10, 2021, in Carlsbad, Calif. (AP Photo/Gregory Bull)
Ben Cherington has already completed one major offseason task, but the Pittsburgh Pirates’ general manager still has plenty of work ahead of him.
On Monday, Cherington took the stage at PNC Park for a press conference to formally announce that Don Kelly had his contract extended and will be the Pirates’ manager moving forward.
One problem solved. Many, many more to go.
Despite six losing seasons to begin his tenure with Pittsburgh, Cherington will handle the Pirates’ offseason as he looks to drastically improve a team that finished in last place in the National League Central in 2025 with a 71-91 record – five games worse than they were each of the two previous seasons.
But despite the poor showing, Cherington feels the Pirates aren’t as far from contending as that record indicates.
“In terms of being able to play in October, I do believe we are close and we’ve got really important work to do,” he said. “It’s not just going to happen by being passive and hoping for it to happen.”
Offense is far and away the biggest need for the Pirates this winter. As a unit, Pittsburgh finished last in the league in runs scored, home runs, slugging percentage and OPS. Of all the players to have at least one plate appearance with the Pirates this season, Spencer Horwitz (118) was the only one to finish with an OPS of at least 100.
“We’ll get into the exact details of that strategy,” Cherington explained. “You never know exactly what opportunities will be there. It’s clear to me we’ve got to improve the roster, and that certainly includes on the position player side.”
Cherington’s track record of acquiring hitters whether in free agency or through trade has been abysmal, but the Pirates’ GM feels like they have a better understanding of the type of players they should be targeting.
“I believe we’re getting more clear all the time on what the combination of traits are that we should be making the best bet on,” he said.
Under Cherington, the Pirates have yet to sign a free agent to a multi-year contract. Additionally, Pittsburgh has largely shied away from trading any of the organization’s top prospects for established big-league help.
With more urgency and an even hotter seat underneath him, both will need to change if the Pirates are serious about getting better in 2026.
“I think we’ve got to be ready to be aggressive in acquisition this offseason whether it’s free agency or trade,” said Cherington. “In our situation we’ve got to be willing to assume the risks of trades because free agency is not an open ocean for us. We’re going to be able to be targeted there and we will be and we’ll try to be able to put ourselves in the best position to do that we possibly can, but if we want to give ourselves every chance, it’s got to be the trade market also.
“We’ve got to be prepared to chase down every single thing that we think has a chance to help this team win more games in ’26, execute on the ones we can get to and just be dogged about it all offseason.”
But part of the reason the Pirates haven’t delivered a multi-year free agent contract – and there are a few – is because of the perpetual stinginess of owner Bob Nutting.
Despite the Pirates’ track record as an organization, Cherington believes there’s enough support from ownership to build a winning team this offseason.
“We’ve got the resources to win. We’ve just got to execute,” said Cherington. “My conversations with Bob recently have been every combination of challenging, productive, difficult at times. I leave every one of them more clear on how we’re both seeing this and what’s important and how we’re going to go about executing. I believe that and we’ve just got to go do it.”
Time will tell if anything changes this offseason or if the precedent that’s been set for decades continues. If Cherington fails to deliver a winning product, this will be his last year as general manager of the Pirates.
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