The Chicago Cubs entered the offseason as an afterthought in the National League Central, with the Milwaukee Brewers maintaining their dominance and the Cincinnati Reds and Pittsburgh Pirates boasting some of the league’s most promising young talent. However, rather than staying idle, the Cubs have been aggressive in their efforts to position themselves as contenders for the division title in 2025.
This winter, Chicago acquired superstar outfielder Kyle Tucker and elite closer Ryan Pressly from the Houston Astros. They are also actively pursuing free-agent third baseman Alex Bregman. If they manage to sign Bregman, it would complete what could be considered an outright raid on Houston’s core talent.
Beyond strengthening their lineup, the Cubs are looking to bolster their starting rotation before the 2025 season kicks off. While they already have a strong staff led by breakout star Shota Imanaga, adding another frontline starter would be crucial for their championship push.
The Cubs could pivot from one Padres ace to the next this offseason
That’s where the San Diego Padres come into play. The Padres are reportedly open to trading their top two starting pitchers, Dylan Cease and Michael King.
Cease has been rumored as a trade candidate for a while, but San Diego has yet to move him, reportedly seeking a significant return. With his contract set to expire after the season and his sights likely set on a massive payday in free agency, teams—including the Cubs—may be hesitant to meet the Padres’ high asking price.
As a result, Chicago could turn its attention to King instead. While not as established as Cease in a starting role, King is still a highly talented pitcher. His trade value is also likely lower, making him a more attainable target.
King’s contract includes a mutual option for 2026, potentially giving the Cubs an extra year of control if he opts in. If Chicago decides that Cease’s price is too steep, a trade for King could be a logical alternative—one that might work well for both sides.