Chicago Cubs president of baseball operations Jed Hoyer is set for a busy offseason. After a disappointing end to their playoff run, the team has several key players heading towards free agency. This lengthy list includes star pitchers Shota Imanaga and Kevin Gausman. Nevertheless, Chicago is also unlikely to bring back outfielders Seiya Suzuki and Ian Happ.
Because of this, Bleacher Report’s Kerry Miller believes the Cubs will soon target Cleveland Guardians star Steven Kwan. The reporter points out that Chicago’s current group of outfielders without Suzuki and Happ is not exactly ideal. As a result, Hoyer and Co. will likely look to bring in at least one player in this position, either in free agency or via a trade.
“[The Cubs] are losing a boatload this winter, including four of the six players who appeared in at least 20 games in the outfield in 2026,” writes Miller. “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.”
While the Chicago Cubs will eye a new outfielder, they are expected to be mindful of spending in this area. Hoyer is more likely to spend more money on pitching this winter. Kwan notably earned just $7.7 million in Cleveland for the 2026 campaign. Although he is set for a pay raise, Miller claims that the outfielder’s 2027 salary should be around $10 million in his last year of arbitration.
Chicago Cubs Could Soon Replace Happ with Steven Kwan
The Chicago Cubs potentially targeting Kwan would certainly make sense. Besides the aforementioned attractive financial details of the star’s contract, he would fit in well in left field at Wrigley Field. Both Kwan and Happ, Chicago’s typical left fielder, are known for their defensive abilities. In fact, both outfielders have won four Gold Glove awards.
Offensively, Happ certainly has more power than Kwan. The current Chicago Cubs star had higher slugging, OPS, and home run totals compared to the Guardians outfielder in 2026. Nevertheless, the versatile Kwan was better in batting average, on-base percentage, and stolen bases. The Cleveland slugger also posted an impressive 5.3 WAR for the current campaign. This was the 17th-best figure in the entire league.
Chicago Expected to Offload Prospects to Land Outfielder
The biggest question Chicago Cubs fans will have about this potential trade is who their beloved team has to give to Cleveland to strike a deal. According to Miller, Hoyer would have to send Jaxon Wiggins and James Triantos the other way. Wiggins was previously viewed as a top-tier prospect. While he is still highly rated within the Cubs organization, the pitcher struggled in 2026.
In fact, Wiggins posted a 7.83 ERA in 18 games with AAA Iowa. Despite this, the ace is still just 25 and is expected to bounce back in 2027. Triantos, on the other hand, is the 11th-rated prospect in Chicago. The versatile slugger has played six different positions throughout his minor league career. He recently slashed a solid .300/.353/.434 in 113 total games in Iowa this past season.
Kwan has been linked with a potential move out of Cleveland for quite a while now. As Miller points out, the Guardians previously traded Josh Naylor to the Arizona Diamondbacks in a very similar contract situation to the current outfielder. The Chicago Cubs should be looking to take advantage of the circumstances.
Cubs Trade Idea Lands $10 Million Outfielder to Replace Ian Happ