What happened: The Chicago Cubs are evaluating another winter trade push for Los Angeles Angels left-hander Reid Detmers after the two clubs nearly completed a deal at the 2026 trade deadline, per Chicago Cubs On SI. Chicago has also emerged as a potential trade fit for Cleveland Guardians outfielder Steven Kwan if Cleveland shops him this offseason, per Cubs Insider. Meanwhile, the Cubs expect to retain their current pitching coaching staff for 2027.

Why it matters: Adding pitching with high-end stuff is Chicago's top offseason priority for the automated ball-strike era as multiple 2026 arms reach free agency, per MLB.com and North Side Baseball. The Cubs are also banking on a rebound from second baseman Nico Hoerner following a down 2026 campaign in the first season of his six-year contract extension. Upgrading the rotation and outfield defense is central to Chicago's push to close the gap in the National League.

What to watch: Chicago's front office will gauge trade prices across the league once the 2026 World Series between the Tampa Bay Rays and Milwaukee Brewers concludes. The Cubs must weigh packaging young trade candidates for controllable arms against pursuing free-agent starters.