4 sudden player opt-outs could reshape the Cubs' offseason plans

The first week of the offseason is often the most procedural of the winter, with players and teams making decisions on options for the season ahead. Most of these decisions are known before the end of the regular season, but as is the case with the Chicago Cubs and Shota Imanaga, there can often be a level of complexity that makes a decision complicated.

Nonetheless, beyond the players with expiring contracts, a handful of potential targets are added to the free-agent market this week. For a Cubs front office that is always looking to improve around the margins, the more options available lead to more paths for Jed Hoyer and Co. to be creative.

Cubs just got four new names to think about after 2026 option decisions

Lucas Giolito - Boston Red Sox

Lucas Giolito declined his end of the 2026 mutual option in his contract with the Boston Red Sox. A former ace for the Chicago White Sox, Giolito posted a 3.41 ERA in 26 starts with the Red Sox last season. The Cubs have loosely been connected to Giolito in recent years, including this past year at the trade deadline, and he figures to be in the tier of free-agent pitchers that the team normally prefers.

Brandon Woodruff - Milwaukee Brewers

Brandon Woodruff has been a staple of the Milwaukee Brewers' starting rotation, but availability has been a question throughout his career. Woodruff made 12 starts with Milwaukee last season after missing the 2024 season recovering from shoulder surgery, and declined his mutual option for the 2026 season. The Brewers are likely to try to bring him back, but given the connection to Craig Counsell and the need for pitching the Cubs have, Woodruff makes a ton of sense.

Pete Alonso - New York Mets

Over the last two years, Pete Alonso has been the white whale of Chicago Cubs rumors. Given Michael Busch's ascension as one of the best first basemen in the National League, the Alonso-to-the-Cubs rumors have cooled. In a world where the Cubs are looking for a designated hitter this offseason, Alonso, who opted out of his deal with the New York Mets, would be an ideal target.

Alex Bregman - Boston Red Sox

After opting out of his deal with the Boston Red Sox, Alex Bregman is going to be connected to the Chicago Cubs this offseason. If the Cubs are trying to look for a way to improve their offense this offseason, or, at the very least, replace Kyle Tucker's impact, Bregman is the easiest path for that upgrade.