The Chicago Cubs are pushing hard for a playoff spot as they vie with the Milwaukee Brewers in the NL Central, a division they haven't won since 2020. Their star player, Kyle Tucker, is set to hit free agency, adding urgency to their quest for postseason success. With President of Baseball Operations Jed Hoyer in the final year of his contract, the pressure mounts to maximize this competitive window.

Starting pitching improvement has been a primary focus, with Shota Imanaga returning strong from injury, and Matthew Boyd showing signs of a career revival. Although Jameson Taillon's performance has been inconsistent, he remains a reliable innings eater. Nonetheless, the Cubs are exploring adding further depth, with Mitch Keller of the Pittsburgh Pirates identified as a key target. Keller's impressive 3.48 ERA and strikeout count make him a compelling option, especially with his contract control through 2028. His recent success against the Brewers enhances his allure as the Cubs approach the trade deadline.