The Pirates are heading into an offseason where payroll math matters, and Mitch Keller sits right in the middle of it.
Pittsburgh already has a projected payroll above $100 million for 2027 before any additions, so moving a high-salary player like Keller would be one way to create room. Keller is set to make about $18.5 million in 2027, the most expensive contract on the Pirates’ books that year.
That figure tops the $15 million each that Bryan Reynolds and Ryan O'Hearn will make. He is in the fourth season of the four-year, $77 million extension he signed on Feb. 22, 2024, and his final season in 2028 will push him above $20 million.
The Pirates have also explored trading Keller before, so this isn’t a brand-new idea. If they decide to revisit it, three clubs stand out as possible fits.
Chicago is the longest shot of the group, but the White Sox could use rotation help heading into 2027. Their postseason run exposed how much they leaned on the bullpen, and that wore them down in the end when they blew a 2-0 lead in the American League Divisional Series against the Cleveland Guardians.
In 2026, their rotation logged the fewest innings in MLB at 674.2, while also putting up a 4.60 ERA, a 1.34 WHIP and a .250 batting average against. Keller would give them a veteran arm they could count on from start to start.
His injury record is also relatively clean, with the right arm teres major muscle injury this season marking the longest stretch he has missed in his MLB career. Chicago doesn’t spend big, but after going from 41-121 in 2024 to an AL Wild Card spot two years later, it may be ready to keep pushing forward.
San Diego is another club that makes sense if the Pirates decide to deal Keller. The Padres’ bullpen was among the best in baseball in 2026, but the rotation was shakier and could look very different in 2027.
Only Joe Musgrove and Randy Vasquez are certain to be back from last season’s group, and both Robbie Ray and Casey Mize struggled after arriving at the deadline. Ray posted a 5.02 ERA and Mize finished at 7.46.
Michael King was their most effective starter across the regular season and postseason, but his $32 million salary in 2027, along with an opt-out, makes his return look unlikely. Keller would cost less and could become a key piece as the Padres try to remake the rotation.
Atlanta is the final team in the mix, and it depends on how much starting pitching the Braves want to add. Chris Sale, Spencer Strider and Spencer Schwallenbach are still there, but Sale will be 38 next season and both Strider and Schwallenbach are dealing with serious injuries.
The Braves have gotten production from Grant Holmes, Bryce Elder and Martín Pérez, but they may still look for more depth this offseason. Keller would fit as a dependable fourth- or fifth-day starter and has stayed healthy for most of his career.
The price tag could be the sticking point, though Pittsburgh could lower that burden by taking on part of the contract to make a deal more workable for Atlanta.
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Mitch Keller Has Become Pittsburghs Toughest Offseason Call
Mitch Kellers 2026 season followed a frustrating arc for the Pirates, beginning with a strong run before his performance slipped and his year ended early with an arm injury. For a club trying to piece together a young pitching staff, that left Pittsburgh staring at one of the winters most difficult decisions: whether to keep a veteran starter who still has a track record of success, or use him as a trade chip while his value and role are both in flux.
The financial piece makes the call even trickier. Keller is still owed significant money in the years ahead, which narrows the market and raises the chances that any deal would have to come with Pittsburgh eating salary just to create flexibility elsewhere. Holding him, though, would mean betting on a rebound from an arm injury and trusting that his place in the rotation can still fit alongside the wave of younger arms the Pirates are trying to develop. [Read more 🡒]
Pirates Contention Window Could Shrink For A Reason Fans Hate
The Pirates came out of a difficult 2026 season with a few bright spots, but the work ahead is already getting complicated. Pittsburgh has roster questions to sort through for 2027, from whether to keep Brandon Lowe in the fold to how it wants to shape the starting rotation after a year that still left plenty unresolved despite some individual success stories.
There is also a broader issue hanging over the sport that could make every front office decision a little messier. If the labor situation turns into a stoppage, the timing would hit a team like the Pirates especially hard, because it would squeeze the runway for a club trying to build around a young core while managing the cost of keeping that window open. [Read more 🡒]