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Mitch Keller is one of the pitchers most rumored to be a potential addition for the Chicago Cubs ahead of the MLB Trade Deadline, and the latest was that the Pittsburgh Pirates' asking price could be one of the reasons why the two teams have yet to make a deal. Even with Keller's rising price, the Cubs may still be the team in the best position to make a trade for the veteran starting pitcher.
In preparation for the MLB Trade Deadline, former MLB general manager Jim Bowden answered fan questions during a recent mailbag for The Athletic. Among the questions that Bowden was asked was who the best Major League-ready position player the Pirates could get in exchange for Keller. The answer was simple as Bowden pointed directly to the top Cubs' prospect, Owen Caissie.
Owen Caissie AGAIN! 😲
— MLB Pipeline (@MLBPipeline) July 9, 2025
The @Cubs' No. 1 prospect has THREE multihomer games in July after launching his 18th for the Triple-A @IowaCubs: pic.twitter.com/TYIxr9Wo0O
Speaking of Caissie, he is on an absolute tear right now with the Iowa Cubs. Caissie has three multi-home-run games in July, and on the season, he has 18 home runs with a 144 wRC+. Caissie is getting hot at the right time, as many believe him to be the prospect who the Cubs would be willing to move ahead of the deadline.
Given that Keller is signed to a team-friendly deal through 2028, the Pirates are in a position where they can get a top prospect for the 29-year-old. Considering the Cubs entered the season by trading Cam Smith for one season of Kyle Tucker, there should be no hesitancy to including Caissie in a trade that would land them a starting pitcher who can stabilize the middle of their rotation for the next several seasons.
On a not directly related, but relevant note, if the Cubs do trade Caissie, it would add another reason why they need to sign Tucker to a contract extension. Otherwise, Smith and Caissie, if a trade for Keller were to be completed, stars elsewhere would be a painful realization. Especially if the Cubs do not win the World Series in 2025.
The silver lining to that aforementioned scenario is that the Cubs would have Keller still. With Jameson Taillon a free agent after 2026, and Shota Imanaga's contract approaching decision time, having Keller penciled into rotation through 2028 would be valuable for the Cubs.