The Chicago Cubs haven’t reached the postseason since 2020. This winter will be crucial as they try to break that drought in 2025. Could president of baseball operations Jed Hoyer fortify a top 10 starting rotation by making a trade with the Chicago White Sox for Garrett Crochet? Chicago finished the 2024 campaign with a 3.77 rotation ERA. That tied the Baltimore Orioles for baseball’s fifth-best mark. Four hurlers made 20-plus starts for manager Craig Counsell: Shōta Imanaga, Justin Steele, Jameson Taillon and Kyle Hendricks. Among this group, Hendricks (6.27 ERA) was the only one with an ERA above 3.27. While Hendricks is no longer under contract, the other three will be back in 2025. So, adding a top pitcher like Crochet would make the Cubs’ rotation tough for opposing teams to manage.

– White Sox receive: outfielder Owen Cassie, shortstop Jefferson Rojas and right-handed pitcher Brody McCullough According to MLB.com, Cassie (second), Rojas (eighth) and McCullough (24th) ranked within the Cubs’ top 30 prospects in 2024. In adding Crochet to their pitching staff, the North Siders would pair him with two other lefties (Imanaga and Steele) at the top of the rotation. The White Sox southpaw’s first year as a full-time starter in 2024 resulted in an All-Star Game selection and 4.7 WAR, per FanGraphs. He posted a 6-12 record with a 3.58 ERA and 1.07 WHIP, along with a 32.3% strikeout rate and 8.0% walk rate. Crochet was one of 11 hurlers to surpass the 200-strikeout plateau, whiffing 209 hitters in 146 innings. He’s under team control through 2026 and is estimated to earn $2.9 million next season.