The Cleveland Guardians are not only facing the end of their season in Game 3 of the ALDS against the Chicago White Sox on Wednesday. It could also mark the end of Steven Kwan’s time with the team.
A subject of trade rumors for almost two years, and without a contract extension that would have kept him with the Guardians long-term, Kwan’s future is more in doubt than it has ever been. When the outfielder was slumping early in the season, it looked like it would be easy to part with him, but after a spectacular second half, his value to the team was made clear.
Bleacher Report analyst Kerry Miller is already linking the Guardians to a big trade with the Chicago Cubs, who would acquire Kwan in exchange for two prospects.
Cleveland Guardians receive: RHP Jaxon Wiggins (Triple-A prospect), UTIL James Triantos (controllable through at least 2032)
Chicago Cubs receive: OF Steven Kwan (arbitration eligible in 2027)
“Steven Kwan made $7.725M in arbitration for 2026. His 2027 salary is very likely to climb north of $10M. And, well, unless it’s for Jose Ramirez, the Guardians don’t like dedicating eight figures to an individual player’s salary. Despite their penny-pinching ways, they just keep making the postseason, winning the AL Central for the seventh time in 11 years. So, if they can turn one year of Kwan into a pair of former second-round picks, history suggests they probably will,” Miller wrote.
Kwan has been one of Cleveland’s best players during his five MLB seasons. A two-time All-Star and four-time Gold Glove winner in left field, he is also a leader, as he was willing to move to center field this season to make it easier on some of the Guardians’ young prospects.
But players like that inevitably want a big contract, and that is not the way Cleveland does business. Fortunately, the Guardians should be set in the outfield going forward with Chase DeLauter and Angel Martinez, and prospects such as Khalil Watson and Jaison Chourio in the minor leagues.
In this proposal, they would also be adding versatile utility player Triantos to the mix. Ranked as Chicago’s No. 11 overall prospect by MLB.com, the infielder-outfielder had a .300/.353/.434 slash line with nine home runs and 27 stolen bases at Triple-A Iowa this season and made his MLB debut with seven games for the Cubs, going 1-for-8.
The headline of the deal would be Wiggins, Chicago’s No. 6 overall prospect, who dealt with elbow inflammation this season. In 2025, the 6-foot-6 righty posted a 2.19 ERA with 97 strikeouts in 78.0 innings, working his way up to Triple-A.
Losing Kwan would be a blow to the fan base, particularly if it follows an early playoff exit, but the Guardians have found a way to remain successful even as some of their top players depart.
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