Trading away a high-priced, notable asset at the MLB trade deadline seems like something every struggling team like the Pittsburgh Pirates should want to do. However, it is always easier said than done when it comes to moving on from a beloved homegrown product. The player in question when it comes to the Pirates is right-handed pitcher Mitch Keller, who is under contract for three more years.
In Ken Rosenthal's deep dive into the situation at hand for The Athletic, he assessed if and will the Pirates actually rip the band-aid off and trade the guy. The argument behind moving on from Keller is to help this team in dire need of bats get something of that variety at the deadline. Trading away Keller would also free up some much-needed payroll for owner Bob Nutting's cheapskate ways.
However, trading away Keller at this time would essentially be Pirates general manager Ben Cherington admitting defeat. We know this season is toast for the Buccos, but there just might maybe be a glimmer of hope come 2026. Could Keller be a piece to help build a winner around Paul Skenes on the mound? My thought is to sell high on a player that the Pirates are not going to extend again.
These are the type of problems an organization can run into when not everyone is properly aligned.
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Ben Cherington may not be for long at the helm of Pirates' front office
If we try to approach this from a logical perspective, Keller is the type of player a struggling team like the Pirates could conceivably move on from. I think the big hold-up here is the amount of years he is still under contract. Had he been playing on an expiring contract, then it should be a no-brainer to move on from Keller. Again, this comes back to the glimmer of hope Cherington is trying to put forth.
What I am getting at is Pittsburgh has more talent than the Pirates' record indicates. The pitching seems to be there, and they supposedly have it for days at the minor-league level. However, it is hard to win games when you cannot score runs with any great regularity, hence the reasoning behind selling on a player like Keller at this time. Would you make a deal? I probably would, but I am not a GM.
In the end, it is hard to see a world where the Pirates are a consistently competitive team with Nutting as the franchise's majority owner. We have seen this franchise draft well and do a decent job of developing its players. The problem is this inherent heaviness that seems to hang over the entire organization from the looming ivory tower overhead. At some point, it may change, but I am not sure.
Holding onto Keller could come back to haunt Cherington if he and the Pirates struggle next season.