Pirates' most expensive player could become their most uncomfortable offseason decision

It wasn't long ago that Mitch Keller was one of the hottest names on the trade market. Around the 2025 trade deadline, he was among the most valuable pitchers supposedly available, with 3.5 years remaining on his contract and a 3.48 first-half ERA standing out on his ledger.

The Pittsburgh Pirates, of course, wound up holding onto the veteran right-hander, which looked prescient for a little bit. He got off to a hot start in 2026, recording a 3.18 ERA and 3.07 FIP through the end of April. By most accounts, he looked like his usual self, flashing frontline starter upside while generally performing like a mid-rotation stalwart.

Then, the collapse came. From May 1 onward, Keller logged a 6.17 ERA while allowing more home runs and walks than ever before, which also coincided with a precipitous decline in his groundball and strikeout rates. The nightmare ended when he was placed on the injured list in early August with a right arm teres major muscle injury, prematurely concluding his campaign.

At this point, it's clear that the Pirates missed their chance to sell high on their most experienced starting pitcher. The question now is whether or not they're willing to sell low.

Pirates face a catch-22 dilemma with Mitch Keller after injury-marred season

Money, as it always is with the Bucs, is the biggest obstacle here. Keller is owed more than $18 million in 2027 and more than $20 million in 2028 before his contract expires. There are absolutely teams that would be thrilled to spend that kind of cash on the 2022-25 version of Keller -- when he tossed more than 150 innings each year and racekd up 10 fWAR -- but it might be hard to sell them on the version we most recently saw.

The future of the Pirates' rotation is already in Pittsburgh, featuring the quartet of Paul Skenes, Jared Jones, Bubba Chandler, and Braxton Ashcraft. Throw top prospect Seth Hernandez into the mix and you've got an elite young staff that just doesn't have room for an expensive, aging veteran.

Still, there is stability that Keller provides that is hard to find elsewhere. He's going to cost a lot of money that could be used on upgrading other areas of the roster, but trading him at this point would likely amount to nothing more than a salary dump. That would be a hard pill to swallow after he was so reliably good for the better part of a half-decade.

Entering the offseason healthier than he was at any point during the season, there's a strong case to be made that the Pirates should hang onto Keller and hope for a reversal of fortunes next year. That course of action would be wise, but only if ownership is willing to continue investing in the roster without sending out money to offset any new expenditures.

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