The Chicago Cubs have some difficult decisions ahead this offseason, and not all of them involve their pitching staff. While adding another reliable starter remains a priority, a potential shakeup in the outfield could give Jed Hoyer an opportunity to address another area of concern.
Cleveland Guardians outfielder Steven Kwan has emerged as an intriguing name to watch. And with Chicago's front office already facing questions about its current roster, the possibility of bringing a four-time Gold Glove winner to Wrigley Field deserves some attention.
Cubs have an intriguing connection to Steven Kwan
There's a difference between a trade rumor that somebody dreamed up on social media and one that comes from a reporter with legitimate connections around baseball.
This one falls closer to the latter.
MLB insider Robert Murray recently identified the Cubs as a potential landing spot for Kwan, whose future in Cleveland has become a topic of offseason speculation. Murray also pointed to an interesting connection between the two organizations.
Cubs general manager Carter Hawkins spent 14 seasons working in Cleveland's front office before joining Chicago. He knows the organization, understands how its baseball operations department approaches roster construction, and has relationships that could help facilitate conversations.
None of that guarantees a trade. It doesn't even establish that Chicago and Cleveland are actively negotiating.
But it does make the Cubs a reasonable team to watch if the Guardians decide they're willing to entertain offers.
And Kwan isn't exactly the kind of player teams stumble across every winter.
Why Kwan could be exactly what Chicago needs
Kwan isn't going to hit 35 home runs or lead the National League in slugging percentage. That's never been his game.
What he does exceptionally well is put the ball in play, get on base and make pitchers work. In 2026, he hit .282 with a .382 on-base percentage, 152 hits and 80 runs scored. He also struck out just 52 times in 637 plate appearances.
Those numbers become especially attractive when considering what Chicago might lose this winter.
Ian Happ and Seiya Suzuki are both approaching free agency. Keeping either could require a substantial financial commitment, particularly with the Cubs expected to pursue pitching upgrades.
Happ hit 24 home runs in 2026, but his .218 batting average wasn't exactly what Chicago wanted from a veteran outfielder. Suzuki provides more offensive firepower, although retaining him could complicate the team's other offseason plans.
Kwan would offer a different approach.
He's not replacing Suzuki's power production. He wouldn't be asked to. Instead, he'd give Chicago a dependable contact hitter who can reach base ahead of the club's bigger bats.
Then there's his defense.
Four consecutive Gold Gloves aren't something a player collects by accident. Kwan has established himself as one of baseball's premier defensive left fielders, and pairing him with Pete Crow-Armstrong could give Chicago an outstanding defensive combination.
The Cubs would have competition for Kwan
Of course, Cleveland isn't obligated to trade him.
Kwan remains under team control through 2027, meaning the Guardians could keep him for another postseason push. However, with free agency approaching and no long-term extension in place, Cleveland has a decision to make.
The Guardians have previously shown a willingness to move established players rather than risk losing them for nothing.
San Diego has also been mentioned as a potential destination, which could complicate Chicago's pursuit.
And here's where things get interesting.
Chicago needs pitching, possibly more than it needs another outfielder. Giving up valuable prospects to acquire Kwan would reduce the resources available for a rotation upgrade.
Hoyer would have to determine whether acquiring an established hitter on a relatively affordable contract outweighs the cost of surrendering young talent.
There's also the possibility of losing Kwan after just one season. Unless Chicago could negotiate an extension, the Cubs would essentially be acquiring a one-year solution.
That's a considerable risk if Cleveland's asking price gets out of hand.
Chicago has an opportunity it shouldn't dismiss
The Cubs don't need to win the offseason headlines. They need to build a roster capable of winning games in October.
Kwan isn't the flashiest name available, and fans hoping for a massive power bat might find the idea underwhelming.
But consider the alternative.
Chicago could spend heavily on pitching, watch Happ and Suzuki depart, and enter 2027 with serious questions about its corner outfield production.
Acquiring Kwan wouldn't solve every offensive concern. It would, however, provide a proven leadoff option, elite defense and another experienced player for a club trying to take the next step.
Whether the Guardians actually make him available remains uncertain.
For now, the connection between Chicago and Cleveland is worth watching. If the Cubs can acquire Kwan without sacrificing the prospects needed to address their pitching staff, this could become one of the more sensible moves of the offseason.
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