Orioles make bizarre U-turn with Cubs in a trade that defies all logic
At this year’s MLB trade deadline, the Baltimore Orioles dealt reliever Andrew Kittredge to the Chicago Cubs in exchange for teenage shortstop prospect Wilfri De La Cruz. But in a wild turn of events, the O’s have reacquired Kittredge from the Cubs for cash considerations.
This is easily one of the most bizarre things you’ll ever see in baseball. It’s almost as if the Cubs just borrowed Kittredge for the summer and sent him back once the season was over. While Kittredge is far from the only player to ever return to his former team, the timing and circumstances surrounding this transaction defies all logic.
Orioles make bizarre U-turn, pull off trade with Cubs for reliever Andrew Kittredge
The Orioles have acquired reliever Andrew Kittredge from the Cubs for cash considerations.
— Robert Murray (@ByRobertMurray) November 4, 2025
In total, Kittredge made 54 appearances last season. He logged 53 innings of work and struck out more than 30% of the batters he faced. The right-hander was also quite effective at keeping the ball on the ground. His ground ball rate of nearly 50% was among the top 20 % in all of Major League Baseball, and the O’s will be hoping for more of the same in 2026.
Kittredge has been a workhorse the past two seasons with more than 120 inning pitched over 128 appearances, all to the tune of a 3.06 ERA and 3.46 FIP. The veteran has six saves during that two-year stretch, but it’s unlikely O’s fans will see him serve as the team’s closer next season.
Kittredge has a club-option for the 2026 season that the Orioles will obviously pick up. Though the actually amount of cash considerations sent back to Chicago as part of deal are unknown, it’s unlikely to greatly affect Baltimore’s free agent pursuit this winter.
One area of concern for the Orioles heading into the offseason was the team’s bullpen. Reacquiring Kittredge certainly helps in that regard, and the O’s have a top-25 organizational prospect to boot. De La Cruz currently ranks 24th among all Orioles prospects according to MLB Pipeline.
But if the Orioles truly want to compete with the New York Yankees, Boston Red Sox, and Toronto Blue Jays next season, it’s going to take more than just a do-over with the Cubs to fix the O’s bullpen.
