Ben Cherington Makes One Promise to Pirates Fans

Cherington spoke with Ken Rosenthal and Evan Drellich of The Athletic about how they must make up for not achieving what they needed to in previous offseasons and bolster their young players with better roster talent overall this winter.

“We’ve got to deliver more to our fans, to everybody who cares about the team, including the people in our clubhouse,” Cherington said. “It really wasn’t that we weren’t trying to do that the last two offseasons. But in retrospect, you can look at those offseasons as conservative in the outcomes.

“It was not necessarily intentionally that way. But that’s how they ended up. And we’ve got an opportunity. We’ve got pitching. We’ve got young talent coming. It’s just that we’ve got to deliver more. It’s time to do that. It’s past time to do that.”

Why the Pirates are Acting with Urgency

The Pirates have Skenes, which is a big part of their desire for wanting to improve the roster, but they also have a strong pitching staff overall and a new pitching coach in Bill Murphy that should make it better.

Pittsburgh brought up four rookie pitchers in right-hander, Braxton Ashcraft, Mike Burrows and Bubba Chandler, plus left-hander Hunter Barco, who will fight for a spot in the starting rotation next season.

They also have veteran right-hander Mitch Keller and got Johan Oviedo back from Tommy John surgery, that kept him out of the 2024 season, and a lat injury, which stopped his return until August this past season.

Jared Jones will also make a comeback in 2026, after missing all of 2025 following internal brace surgery, giving the Pirates eight different starting pitching options.

The Pirates also have a solid bullpen, with the likes of right-handers in Justin Lawrence, Isaac Mattson, Carmen Mlodzinski and Dennis Santana.

They excelled as a pitching staff in 2025, with the third least home runs allowed (153), fourth lowest WHIP (1.22), seventh lowest team ERA (3.76), the seventh least walks (473) and the eighth lowest opposing batting average (.236).

Pittsburgh also led the MLB in shutouts with 19, two more than both the two second place teams in the Detroit Tigers and Philadelphia Phillies, who had 17.

The Pirates main issues last season came at the plate, as they served as one of the worst hitting teams in baseball.

Pittsburgh posted the lowest slugging percentage (.350) and OPS (.655), the third lowest batting average (.231) and the eighth lowest on-base percentage (.305) in 2025.

They also scored the least runs (583) and drove in the least RBIs (561), both lower than the 43-119 Colorado Rockies. They also hit the least home runs (117), 31 home runs less than then second-lowest team in the St. Louis Cardinals at 148 home runs, and had the seventh most strikeouts (1,422).

If the Pirates do add to their hitting and it improves, they could end their decade long absence from the playoffs and finally become a contending team.

Will the Pirates Add this Offseason?

The Pirates historically have had one of the lowest payrolls in baseball under owner Bob Nutting since he took over in 2007, ranking in the bottom five teams in 16 of the 19 seasons in his teenure.

Pittsburgh has also spent little in free agency, with their record signing at three years, $39 million for left-handed pitcher Francisco Liriano in December 2014.

The Pirates also haven't signed a free agent position player to a multi-year deal since John Jaso, who signed a two-year, $8 million deal on Dec. 23, 2015, and the last free agent to a multi-year deal since right-handed starting pitcher Iván Nova, who signed a three-year, $26 million deal on Dec. 27, 2016

Cherington said at the general manager meetings in Las Vegas two weeks ago that the team is more "flexible" for trades and free agent signings and will take a more "aggressive" approach in years past.

While the Pirates haven't signed anyone, recent reports from Jeff Passan of ESPN and Rosnethal show their interest in top free agents that would bolster the team.

This includes NL MVP finalist Kyle Schwarber, who hit 56 home runs in 2025, Japanese superstars in Munetaka Murakami and Kazuma Okamoto, plus other bats in first baseman Pete Alonso, second baseman Jorge Polanco and slugger Ryan O'Hearn.

Pittsburgh fans won't get their hopes up until a signing comes through, but the early signs of free agency are, at the very least, encouraging.