Orlando, FL – The Chicago Cubs arrive at the MLB Winter Meetings with a clear mandate: bolster a roster that achieved its first 90-plus win season since 2018. The front office, led by President of Baseball Operations Jed Hoyer, is actively pursuing upgrades across three primary avenues: free agency, the trade market, and international signings, with pitching identified as the paramount priority.
Financial Flexibility Fuels Aggressive Pursuit
The Cubs enter the 2026 season with considerable financial muscle, reportedly possessing between $45 million and $50 million in payroll flexibility, complementing their current commitment of $190 million. This substantial room allows Chicago to be aggressive in their pursuit of impact talent, particularly in the pitching department.
Frontline Arms Top Free Agency Wish List
The free-agent pitching market presents several intriguing targets for the North Siders. High on their list is 27-year-old Japanese right-hander Tatsuya Imai, hailed as a projected power arm from the Pacific Rim, drawing comparisons to talents like Shohei Ohtani and Yoshinobu Yamamoto. Following the successful integration of Shota Imanaga, the Cubs' brass views adding another prominent foreign pitcher like Imai as a strategic "layup." However, the acquisition comes with a significant caveat: a posting fee that could range from 15 percent to 40 percent of his eventual contract. Imai faces a January 2 deadline to sign with a Major League team or return to Japan for the next season. Marquee Sports Network contributor Bruce Levine has been vocal in his advocacy for the Cubs to sign Imai, stating, "“(Imai) is the best pitcher out there … this is your guy.”"
Another significant target is 30-year-old right-hander Zac Gallen, a durable top-of-the-rotation presence who has averaged six strikeouts per game over his seven-year MLB career. Sources indicate that the Cubs and Gallen have engaged in "several serious meetings" regarding a long-term deal. While Dylan Cease, another notable name, recently signed a seven-year, $210 million deal with the Toronto Blue Jays, taking him off the market, Gallen remains a prime option for Chicago to anchor their rotation.
Beyond frontline starters, the Cubs are also looking to reinforce their bullpen. Re-engaging with relievers such as Brad Keller and Caleb Theelbar is on the agenda, with a focus on acquiring power arms capable of high spin rates and velocity, aligning with the organization's emphasis on modern pitching metrics.
Impact Bat Sought at Third Base
On the offensive side, the Cubs are rekindling their interest in veteran third baseman Alex Bregman. The team previously pursued Bregman last winter, but he ultimately opted for a three-year, $120 million offer with two opt-outs from the Boston Red Sox over Chicago's four-year, $115 million proposal. League sources suggest that Cubs leadership has reconnected with Bregman's agent, Scott Boras, to assess the viability of bringing the infielder to Chicago. The length of the contract is expected to be as crucial as the annual value, which is projected to exceed $30 million per season.
Trade Market Explores Young, Controllable Arms
The trade market offers another avenue for the Cubs to acquire pitching, with several young, controllable arms reportedly on their radar. Washington's MacKenzie Gore, Minnesota's Joe Ryan, and Miami's Edward Cabrera are all strike-throwing pitchers with multiple years of team control remaining – Gore and Ryan with two years, and Cabrera with three.
The Cubs previously attempted to acquire these pitchers last summer, but discussions stalled due to high asking prices, which included top prospects such as Cade Horton, Owen Caissie, and Moisés Ballesteros. Horton, in particular, had a breakout 2025 season, finishing second in the National League Rookie of the Year voting, which has likely only increased his value. Caissie and Kevin Alcántara are anticipated to feature prominently in the Cubs' outfield mix alongside veterans Seiya Suzuki, Pete Crow-Armstrong, and Ian Happ, while Ballesteros is expected to receive ample at-bats as a catcher and designated hitter.
International Market: More Japanese Talent
While Tatsuya Imai stands as the "jewel" of this year's international class, the Cubs are also monitoring other overseas talents. Japanese third baseman Munetaka Murakami is a power-hitting option the Cubs could consider if negotiations with Alex Bregman falter. Murakami possesses 30-plus-homer potential, but some clubs are reportedly concerned about a recent drop in his extra-base hits, from a high of 78 in 2022 to just 34 last season. His defense and speed are not considered strengths, and there are questions about how his left-handed power profile would translate to Wrigley Field's gap-to-gap alleys. Another Japanese player, 29-year-old right-handed power hitter Kazuma Okamoto, is also on the Cubs' radar, though his home run total saw a significant dip last season, partly attributed to an elbow injury. Jed Hoyer's extensive expertise in Japanese leagues will be invaluable as the Cubs navigate the complexities of acquiring talent from the Far East.
As the Winter Meetings unfold in Orlando, the Chicago Cubs are clearly signaling an aggressive approach to upgrade their roster, focusing on key pitching additions and an impact bat to solidify their position as contenders for the 2026 season.
