The Chicago Cubs have a long list of free agents this offseason. 

And a lot of those free agents will have a strong market this winter. 

Kevin Gausman, Clay Holmes, Ian Happ, Seiya Suzuki, Matthew Boyd, Carson Kelly, and Shota Imanaga were all listed in Jim Bowden’s top-40 free agents for this offseason. That means it’ll be difficult to bring back all of those players in free agency. 

Bowden agrees, listing only two of those players as the best fit for the Cubs. Here are the two Cubs players Bowden believes could return to the team for the 2027 campaign. 

Happ has been around the Cubs organization for a long time. This is the organization that selected him ninth overall in the 2015 MLB Draft, and it is the only organization he has known in his professional career. 

However, Happ’s poor 2026 season could end his Cubs tenure. The switch-hitting outfielder put together the worst offensive numbers of his career in 2026. He slashed .218/.326/.412 with 24 home runs and 68 RBI across 156 games. 

Now the Cubs are probably open to a reunion with Happ if the veteran takes some sort of “hometown discount.” The team likely can’t rely on him to be a full-time left fielder next season, as his numbers from the right side were not competitive. He hit just .145 with four home runs against left-handed pitching this past year, compared to a .241 batting average and 20 home runs against right-handed pitching. 

Bowden lists the Cubs and Reds as the two best fits for Happ. He predicts the four-time Gold Glove winner to sign a two-year, $45 million deal this offseason. 

Shota Imanaga has actually posted solid all-around numbers in his three years wth the Cubs. 

In 2024, he posted a 2.91 ERA, 1.021 WHIP, and 174 strikeouts over 173 ⅓ innings pitched while finishing fifth in National League Cy Young voting. In 2025, Imanaga posted a 3.73 ERA, 0.988 WHIP, and 117 strikeouts over 144 ⅔ innings pitched. In 2026, the southpaw posted a 3.77 ERA, 1.096 WHIP, and 174 strikeouts over 174 ⅓ innings pitched. 

While those pitching numbers are solid, the home run problems held Imanaga back from reaching his full potential. The Cubs left-hander allowed 27 home runs in his rookie season, 31 home runs in 2025, and 35 home runs this past year. 

Still, Bowden believes that Imanaga could return to Chicago. He lists the Cubs, Astros, and Giants as the best fits for the Japanese southpaw and projects that he will sign a three-year, $69 million contract in free agency.