Ben Cherington’s first official offseason move signals more mediocrity for Pirates

Here we go again.

Emma Lingan

Chicago White Sox v New York Yankees / Ishika Samant/GettyImages

The Pittsburgh Pirates made their first official addition of the 2025-26 offseason on Monday, claiming outfielder Will Robertson off waivers from the Chicago White Sox and designating Ryan Kreidler for assignment in a corresponding move.

Robertson is a 28-year-old outfielder who has yet to make a real MLB impact. He’s bounced around the minors and projects as a Quad-A type player – a solid Triple-A performer, but one who is unlikely to provide meaningful production in the Majors. He is a fringe depth piece, not a difference maker. His solid, yet unspectacular offensive numbers at Triple-A don’t project to carry over against MLB pitching. (Sound familiar, Pirates fans?)

For a franchise desperate for legitimate Major League talent, opening the offseason with a waiver claim that does nothing to upgrade the big-league roster reinforces the perception that the Pirates are once again prioritizing cheap volume over quality. Fans wanted Cherington to start aggressively, namely by improving the lineup's contact profile. Instead, he went scraping the bottom of the barrel – again.

It's a repeat of a frustrating pattern in line with Cherington's past offseasons. From 2021-24, his early offseason moves included waiver claims or DFA pickups like Canaan Smith-Njigba, Liover Peguero, Ryan Vilade and others who barely moved the needle. Each year, these “depth” players eat up 40-man spots that could be used for legitimate upgrades.

Will Robertson waiver claim is just more of the same for Ben Cherington's Pirates

At best, Robertson is another interchangeable outfield piece who might hit .220 in a pinch. At worst, he’s just a body to fill space on the 40-man.

Even if it’s a minor move in isolation, optics matter – especially coming off another losing season. For a fan base starving for a sign that the organization is serious about contending, opening the offseason with a waiver claim from a non-contender feels like business as usual for a front office allergic to ambition.

Claiming Robertson off waivers fits Cherington’s now-familiar pattern of chasing low-cost, low-upside roster fillers instead of aggressively pursuing real upgrades. It’s not the move itself that frustrates fans, but rather what it represents – another offseason beginning with the same small-market complacency that has defined the Cherington era in Pittsburgh.

Emma Lingan

Emma Lingan is an MLB Staff Writer for FanSided primarily covering the Pittsburgh Pirates. She has been covering baseball for more than a decade dating back to her time as a student at Wake Forest University, and she has won two gold medals as a member of the U.S. National Team delegation (2016 Pan-American Championships & 2017 World Baseball Classic). She is also a credentialed NHL reporter and a member of the Professional Hockey Writers Association. You can follow her @Emma Lingan on Twitter, Instagram and TikTok.