Chicago Cubs trade proposal targets replacement for Happ or Suzuki

The Chicago Cubs will have a lot to do this offseason. Not only do they need to figure out a way to out do the NL Central Division-dominant Milwaukee Brewers, but they have to do that while replacing a good chunk of their roster.

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The Cubs’ entire end-of-season starting rotation could be leaving via free agency, as well as about a third of their bullpen. On the position player side of things, corner outfielders Ian Happ and Seiya Suzuki, catcher Carson Kelly, and bench outfield assets Michael Conforto and Tyrone Taylor could also be lost.

In the case of the team’s left fielder and right fielder, Chicago could very well find themselves in a spot where they’ll have to find replacements for both veteran contributors. The organization does have some quality prospects working their way up the system—Josiah Hartshorn, Kane Kepley, Ethan Conrad—but none are realistic options for 2027.

Cubs trade with the Guardians?

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Seeing this potential dilemma, Kerry Miller of Bleacher Report recently floated out an idea that could help address the Cubs’ outfield needs, for at least the coming season—a trade with the Cleveland Guardians for Steven Kwan, who will become a free agent at the end of the 2027 season.

Miller proposes a two-for-one deal where the Cubs send over pitcher Jaxon Wiggins and infielder James Triantos for the four-time Gold Glover.

Per Miller:

“On the Cubs’ side of this one, they are losing a boatload this winter, including four of the six players who appeared in at least 20 games in the outfield in 2026. Pete Crow-Armstrong in center is a fantastic starting point, but Matt Shaw in right and either Justin Dean or Kevin Alcantara in left figures to be the plan as currently constructed.

‘Losing a boatload’ does also mean ‘has money to spend.’ But trading for one year of Kwan at $10M-$12M would allow them to do their real spending on the pitching staff, where they need it most.”

Kwan to Chicago?

The 29-year-old Kwan is an elite defender, like Happ in left field, but has more consistency in his offensive production. He doesn’t have Happ’s power, but he’s a well-above league-average hitter with a lifetime .282 average, double-digit stolen bases in each of his five full years in the majors, and a career .357 on base percentage. Last season, the lefty slashed .282/.382/.349.

Kwan is also eligible for arbitration and that will likely see his salary go from $7.7 million to $10-$12 million—which would still be about half of what Happ made in 2026.

The big issue with this proposed Cubs-Guardians trade is whether one year of Kwan is worth the Cubs’ best (or second best) pitching prospect and a well-regarded Top 12 prospect. That’s an especially tough assessment to make when considering that, because of looming labor issues, there’s no guarantee on how much of the 2027 season will actually be played.

But Kwan is a smart idea, anyway. Maybe at a cheaper price it makes more sense. The Guardians, also dreading the unknown of 2027, could be looking to dump some salary and, therefore, take less for their left fielder/center fielder.

Time will tell how all this plays out.

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