The Chicago Cubs and president of baseball operations Jed Hoyer have put together an impressive offseason, signaling a clear shift toward a win-now approach.
After a slow start to the MLB offseason, Chicago made its first major move by completing a trade with the Miami Marlins for young starting pitcher Edward Cabrera. In exchange, the Cubs parted with top outfield prospect Owen Caissie, a decision that underscored their willingness to sacrifice future assets to improve the current roster.
Chicago followed that move with an even bigger splash, signing star third baseman Alex Bregman to a five-year, $175 million contract. Much like last offseason, the Cubs found themselves competing with the Boston Red Sox for Bregman’s services, but this time Chicago emerged victorious, landing one of the premier free agents on the market.
The Cubs weren’t done dealing with Boston. According to the MLB transactions log, Chicago signed 24-year-old shortstop and utility infielder Karson Simas to a minor-league contract earlier this week, adding organizational depth while taking a low-risk flier on a former Red Sox prospect.
Simas, a 25th-round selection in the 2019 MLB Draft, spent the last seven seasons in Boston’s system but never reached the major league level. Across 334 minor league games, he posted a .222/.302/.300 slash line with nine home runs and 111 RBIs. While the numbers are modest, the Cubs appear hopeful their development staff can help unlock more from the young infielder.
The move won’t significantly impact Chicago’s major league roster, but it reflects a proactive front office approach. If Simas doesn’t develop as hoped, the Cubs can move on with minimal cost.
More broadly, Cubs fans have plenty of reason for optimism. After operating conservatively in recent seasons, the franchise has clearly changed course. The additions of Cabrera and Bregman, particularly the creative use of deferred money in Bregman’s deal, demonstrate a renewed commitment to contending.
Chicago remains active as the offseason continues, with speculation linking the Cubs to additional pitching help, including Arizona Diamondbacks ace Zac Gallen. While such a move appears unlikely, it’s clear the front office is still exploring opportunities.
With Hoyer aggressively reshaping the roster, expectations around the organization have shifted. The Cubs appear determined to compete at a high level, and the outlook for the 2026 season is significantly brighter than it was just weeks ago.
