Pirates lose ideal Mitch Keller destination after Cardinals' trade splash

Over the last year, there has been so much trade smoke around Mitch Keller; after all, unloading his contract might be a logical route to lead the Pirates to more offense. One destination that made sense for both sides was Boston, a team with a surplus of young outfielders and a need for a starting pitcher. Unfortunately for Pittsburgh, the Red Sox just completed a deal to acquire Sonny Gray from the Cardinals. That all but ends any possibility of the two teams matching up on Keller.

The Red Sox got Gray without touching their outfield depth by dealing two young arms in Brandon Clarke (No. 5 MLB Pipeline's outdated list, and his shine has worn off slightly in recent weeks) and Richard Fitts. The trade also comes with $20 million from St. Louis to help pay down the $35 million Gray is owed in 2026.

Losing Boston as a trade partner for Keller really hurts the Pirates' offseason plans. A dream scenario would have been acquiring Wilyer Abreu for Keller. That would have given Pittsburgh a young, controllable outfielder with a 110 wRC+ and a 2.4 fWAR, while also unloading Keller's expensive contract from the payroll.

Pirates lose ideal Mitch Keller trade destination with Red Sox acquisition of Sonny Gray.

While the Pirates still could move on from Keller this offseason to open more financial flexbility, losing the Red Sox as a trade partner makes it much more difficult. Although there is now one fewer starter off the market, Boston was a key team to watch out for in the Keller sweepstakes.

With the Red Sox no longer a factor, the Pirates must look elsewhere. Other teams that make sense for Keller include the Cubs (had reported interest at the trade deadline), Braves, Orioles (just added Taylor Ward and have young outfielders), Astros, Padres, and Diamondbacks.

The next best organization to emerge as the ideal Keller destination has got to be the Orioles. They need pitching badly, and the Pirates could secure a young outfielder like Colton Cowser in a potential deal. While Cowser did have a down year in 2025, there is still a lot of talent in the tank for him to rebound. He also dealt with a lot of injuries, so when healthy, he could be that left-handed power bat Pittsburgh needs. If the Pirates expect Baltimore to eat a significant portion of Keller's salary, they may have to aim lower to other outfield targets (Heston Kjerstad or Enrique Bradfield Jr., for instance).

Losing Boston as a potential trade partner really complicates the Pirates' offseason plans. Keller remains a very valuable trade chip on the market that could land them their desired controllable bat. The path to dealing Keller just got harder, and hanging on to him now seems like a more realistic outcome.