Chicago Cubs' Three Best Trade Pieces This Winter

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With the winter meetings for Major League Baseball approaching, the Chicago Cubs could easily be one of the more active teams in the trade market.
After ending a four-year playoff drought this past season, the team is determined to ensure their first postseason appearance since 2020 isn't a one-off.
Chicago has room on their roster to add more free agents. They have re-signed starting pitcher Shota Imanaga to a qualifying one-year deal. Also joining the Cubs is relief pitcher Phil Maton.
Cubs sign RHP Phil Maton to a 2-year deal. pic.twitter.com/Rw6okUae0I
— MLB (@MLB) November 25, 2025
Jordan Bastian with MLB.com said, "The top priority for the Cubs heading into this offseason was to add to the front-end of the rotation and bring in multiple arms for the bullpen." He further added that "Adding one more bona fide starting pitcher (Ranger Suárez, Michael King, Tatsuya Imai, and Zac Gallen have been linked to the Cubs) would really strengthen that group."
The Cubs have yet to sign or officially move on from free agent outfielder Kyle Tucker. But the highly coveted player is likely out of Chicago's price range for 2026 and beyond.
Thus, the Cubs may explore other options, including trading for starting pitching depth, bullpen arms, and additional infield depth. Here is a look at the three best potential trade pieces for Chicago this winter.
Seiya Suzuki, OF

The Tokyo, Japan native recorded 32 home runs and 103 RBIs for the Cubs in 2025. Suzuki's .804 on-base-percentage was among the top 50 in the league.
Chicago's right fielder had three home runs and five RBIs in the postseason between both series against the San Diego Padres and the Milwaukee Brewers. However, Suzuki only hit better than .300 in one postseason appearance out of 10 for the Cubs.
Seiya Suzuki drives in Kyle Tucker 💪
— Marquee Sports Network (@WatchMarquee) May 16, 2025
Cubs lead 6-2! pic.twitter.com/KlQUi4nh5g
Playing on the last season of his five-year deal that Suzuki agreed upon in 2022, the 32-year-old becomes lucrative trade bait for a team that needs a veteran outfielder to round out their lineup.
Suzuki could fetch Chicago either a relief pitcher in Travis Sykora of the Washington Nationals or Cade Smith of the Cleveland Guardians. The Cubs could make a second deal in less than a year with the Nationals or the Guardians, as both Washington and Detroit traded with Chicago ahead of the 2025 MLB trade deadline.
Miguel Amaya, Catcher

The Cubs did not tender Reese McGuire, who filled in for Chicago as their backup catcher. According to The Athletic, one of the other teams in the league that is looking to add a catcher is the Houston Astros.
Chicago and Houston were trade partners a year ago when the Cubs acquired Tucker. Here, for the second winter in a row, the Cubs and Astros could be perfect trade partners again.
Amaya could earn Chicago a return of an infield bat like Shay Whitcomb, who is listed at both second and third base. The two-year veteran won't turn 28 until the end of next season.
Houston could also offer Brian King, a 29-year-old lefty who struck out 69 batters in relief during the 2025 season. Just like Whitcomb, King has also spent two seasons with the Astros and could be worth the swap with the Cubs for Amaya.
Colin Rea, Pitcher

Not only has this Cubs player played for the last three playoff opponents the Cubs has faced (the Brewers, Padres, and the Miami Marlins), but he is in the middle of his second stint with Chicago. Rea is 35 years old but can add depth to another team's pitching staff.
After appearing in both Game 1s this postseason for the Cubs, Matthew Boyd may be less likely to be traded. Yet, moving on from Rea again may make Chicago better in the short and long run.
Trading Rea, who went 11-7 with an ERA of 3.95 in 2025, may entice another big league team to trade outfield or bullpen depth to the Cubs. The Tampa Bay Rays could give Chicago Hunter Bigge, who, at 27, would be a rehab project in winter ball.

Chicago could also look at former Cubs player Christopher Morel. The veteran utility man was highly liked by fans before being traded to Tampa in the middle of the 2024 MLB season.
Morel belted 90 home runs and racked up 168 RBIs during his tenure with the Cubs. Chicago would regain a trusted bat, quality defender, and respected player in the dugout.
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Scott Conrad is a Beat Writer for Chicago Cubs On SI, part of the Sports Illustrated Network. He is also a Contributor for the Chicago Sky and Washington Wizards On SI as well as Niner Noise and The View from Avalon on FanSided. Scott grew up in the suburbs of Chicago, primarily Lombard and Naperville, Illinois, and attended Cubs games regularly when he attended Neuqua Valley High School. He graduated from Ball State University with a degree in advertising. His passion to be a sports journalist started in middle school. In 2015 & 2016, Scott was a Correspondent for the Tampa Bay Times covering high school football games. He is also a youth volleyball coach and a two-time published author.