The Chicago Cubs could be looking to make a big move this offseason. 

The Cubs have several holes they need to fill before Opening Day. That’s because they have a long list of free agents who could leave this winter. Players like Ian Happ, Seiya Suzuki, Kevin Gausman, Shota Imanaga, Matthew Boyd, Carson Kelly, and Clay Holmes could all find new homes this offseason. 

Those potential free agents could force the Cubs to make a pretty significant trade to upgrade their roster for 2027. Here are three players the front office could be looking to trade for in the coming months. 

The Cubs have already been linked to Steven Kwan this offseason. MLB insider Robert Murray believes the North Siders could be one of the teams interested in trading for Kwan, with both Happ and Suzuki set to hit free agency. 

Kwan could make a lot of sense as a potential trade target for the Cubs. He’s an excellent contact hitter and a top defender in left field. The Guardians outfielder is a four-time Gold Glove winner.  

The Cubs will need to replace both Happ and Suzuki this offseason if both leave in free agency. That’s where Kwan comes in. Although he is in the final year of his deal with the Guardians, he would be a nice fit. 

The Cubs were reportedly close to landing Reid Detmers at the trade deadline before things fell through. With the team potentially needing pitching help with Imanaga, Gausman, Boyd, and Holmes all set to test the open market, the front office could revisit those trade talks with Detmers this offseason. 

Detmers would obviously be a really strong addition. He is coming off the best season of his career in 2026, posting a 3.36 ERA, 1.038 WHIP, and 211 strikeouts across 185 innings pitched. The southpaw also won’t become a free agent until after the 2028 season. 

That means the Cubs would have him for all of 2027 and 2028. Since the front office has likely already done its homework on Detmers, there could be a deal here. 

There were some rumors at the August trade deadline that the Seattle Mariners were listening to offers on George Kirby. While nothing eventually transpired, the Mariners could see what teams have to offer for the All-Star pitcher. 

It obviously wouldn’t be cheap to trade for Kirby. He won’t be a free agent until after the 2028 season and has posted consistent numbers throughout his career. The right-hander has a career 3.74 ERA and 1.173 WHIP over 812 ⅓ innings. 

If the Cubs want to lock down a controllable starter, they could call the Mariners about Kirby. He would be a top-of-the-line starter.