Oct 20, 2026 8:30 PM

As free agency looms for several key starters, the North Siders may leverage deep front-office ties to land Cleveland’s All-Star contact specialist in another blockbuster move.

The Chicago Cubs haven’t shied away from making big moves in each of the past two offseasons. 

Before the 2025 season, the Cubs made a blockbuster deal to acquire Kyle Tucker. They traded Isaac Paredes, Cam Smith, and Hayden Wesneski to improve a team that had World Series aspirations. 

Before the 2026 season, the Cubs made another bigger trade to acquire Edward Cabrera. The team needed some pitching help, so the front office traded away its top prospect in exchange for a rising pitcher. 

While neither move has really panned out for the Cubs, the front office clearly isn’t afraid to make trades to improve the roster. It happened before the 2025 season. It happened again before the 2026 season. 

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With the Cubs potentially losing a handful of free agents this offseason, another big trade could be in the works. Players like Ian Happ, Seiya Suzuki, Kevin Gausman, Shota Imanaga, Clay Holmes, Carson Kelly, Tyrone Taylor, and Matthew Boyd could all leave in free agency. 

That could force the Cubs to make a trade to replace some of those players. 

One of the top players on the trade market this offseason could be Cleveland Guardians outfielder Steven Kwan. If the Cubs lose Happ and/or Suzuki in free agency, Kwan could be an ideal replacement for one of those outfielders next season. 

A few weeks ago, Bleacher Report actually predicted the Cubs would trade for Kwan this coming offseason. They had the North Siders sending two prospects (Jaxon Wiggins and James Triantos) in exchange for the two-time All-Star. 

There is now another report from an MLB insider that links the Cubs to Kwan again. Robert Murray reported that the Guardians could be looking to trade the outfielder this offseason and explicitly mentioned the North Siders as a potential fit. 

“Cubs general manager Carter Hawkins spent 14 seasons with the Guardians before coming to Chicago,” Murray wrote. “He has deep ties and relationships within Cleveland’s organization, which would only help the communication and negotiations. And he would surely know what Kwan brought behind the scenes in addition to what he provides on the field.”

Kwan would be a good fit for a Cubs team that needs outfield help. He has been one of the most consistent left fielders in baseball over the last few seasons and is coming off another all-around productive season in 2026. 

The two-time All-Star batted .282 with three home runs, 21 doubles, three triples, 32 RBI, and 10 stolen bases across 151 games. Those solid numbers came despite a poor start to the season for Kwan, where he hit .206 with 10 extra-base hits in his first 72 games. He then went on to hit .346 with 17 extra-base hits over his final 79 contests. 

Kwan’s 5.3 WAR this past season was also the second-highest of his career. He finished in the 64th percentile in Batting Run Value and in the 84th percentile in Fielding Run Value. His above-average contact skills, combined with his plus defense, were at the forefront of another solid campaign. 

Kwan to the Cubs could absolutely happen this offseason, with the outfielder in the final year of his deal with the Guardians. 

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