Chicago Cubs Propose Major Trade, Sending 3 Prospects for All-Star Ace

After failing to secure a postseason berth in 2024 despite the hiring of Craig Counsell, the Chicago Cubs are considering trades to bolster their rotation ahead of Opening Day 2025.

In a discussion of possible trade packages involving Chicago White Sox pitcher Garrett Crochet, Bleacher Report’s Kerry Miller put forth a proposal that would see Crochet joining the Cubs.

The suggested deal would have the Cubs acquiring left-handed pitcher Garrett Crochet, while the White Sox would receive outfielder Owen Caissie, shortstop Jefferson Rojas, and right-handed pitcher Brody McCullough. According to Miller, “The Cubs possess the necessary prospect capital to make a vital move.

Although they lack a top-20 overall prospect, they do have eight players ranked among MLB.com’s top 100.” He emphasized that if the Cubs are willing to trade two of these prospects for Crochet, they could potentially surpass the Seattle Mariners to become the top rotation heading into 2025.

All three players—Caissie, Rojas, and McCullough—are recognized as top 30 prospects in the Cubs’ system. As the White Sox go on a lengthy rebuilding process, acquiring these young talents could be immensely beneficial. USA Today’s Bob Nightengale noted in September that the White Sox are expected to trade Crochet.

Nightengale reported, “While White Sox starter Garrett Crochet is interested in a long-term contract extension, the team remains committed to trading him this winter, with the Philadelphia Phillies among the interested parties.”

The Cubs are likely not the only team eyeing Crochet. He is arbitration-eligible in 2025 and 2026 and was named an All-Star in 2024 during his first season as a starter, making 32 appearances with a 3.58 ERA.

Miller concluded, “While there are better aces available than Steele or Crochet, having Imanaga as a No. 3 starter, Taillon at No. 4, and Assad as the fifth option would position them as the team to beat in the NL Central, if they aren’t already.”