Ben Cherington Reveals Why This Offseason Is Different For Pirates

After finishing 20 games below .500 and last in the NL Central this year, the Pittsburgh Pirates have some work to do this offseason.

Fortunately, it sounds like general manager Ben Cherington has more wiggle room to make moves than in years past, especially after freeing up some payroll and roster space at the MLB Trade Deadline last summer.

At the GM meetings in Las Vegas this week, Cherington claims the Pirates have “more flexibility than we’ve had in other offseasons than I’ve been in Pittsburgh,” per FanSided’s Robert Murray.

This is Cherington’s seventh winter with the Pirates, so that’s saying something. The club’s lack of flexibility appeared to hamper him in years past, limiting him to minor moves that failed to meaningfully upgrade the roster.

Notes from the GM Meetings:

– Pirates will not trade Paul Skenes.
– Braves offseason priorities.
– Brewers’ stance with Freddy Peralta.
– Padres interested in retaining Luis Arraez.
– Anthopoulos on Kurt Suzuki.
– Cubs prioritizing pitching over hitting. https://t.co/eYhr2LnPzB

— Robert Murray (@ByRobertMurray) November 12, 2025

Cherington has not signed a free agent to a multi-year deal since arriving in Pittsburgh, but that could be about to change this offseason. According to MLB insider Ken Rosenthal, the Pirates have indicated to other teams that they’re looking to spend more and be more aggressive this winter.

Pittsburgh’s GM also continued to dismiss the Paul Skenes trade rumors that have been swirling early in the offseason. “He is going to be a Pirate in 2026,” Cherington claims.

If Cherington uses his new flexibility to add some offense to a lineup that ranked last in MLB in scoring this season, Pittsburgh will be in much better shape heading into 2026 and might compete for a playoff spot.

More Pirates: Pirates GM Details Conversations With Paul Skenes Amid Trade Rumors