Cubs Predicted To Trade For Guardians Outfielder

The Chicago Cubs have gone two consecutive offseasons of making a big trade. 

Before the 2025 season, the Cubs traded Hayden Wesneski, Isaac Paredes, and Cam Smith for superstar Kyle Tucker. The team lacked a true star at the top of its lineup, so the front office swung big. 

Before the 2026 season, the Cubs traded No. 1 prospect Owen Caissie for starting pitcher Edward Cabrera. Chicago was looking for a young, controllable starting pitcher and went out to acquire Cabrera from the Miami Marlins. 

This offseason, the Cubs could be looking to make another big move. 

The North Siders have some holes that they will need to address before the start of the 2027 season. Pitching is obviously going to be a big focus  in the offseason with so many starters set to hit free agency. 

Kevin Gausman, Shota Imanaga, Matthew Boyd (mutual option), and Clay Holmes (player option) will all likely test the waters in free agency. Gausman could return back to Toronto, while Cubs insiders believe that the writing is on the wall for Imanaga in Chicago.  

Pitching isn't the only focus for this team, as the outfield is, too. The Cubs have multiple outfielders who will be free agents, including Ian Happ, Seiya Suzuki, Michael Conforto, and Tyrone Taylor. 

The two biggest names on that list are Happ and Suzuki. Both occupied the corner outfield spots for this Cubs team throughout the 2026 season. Now both could depart in free agency, leaving the team with no clear replacement at left and right field. 

However, the Cubs could get creative in trying to fill that void. 

Bleacher Report put together a trade package that would help the Cubs land two-time All-Star and four-time Gold Glove winner Steven Kwan. Chicago would land Kwan and send Jaxon Wiggins and James Triantos to Cleveland in return. 

This would be a very interesting deal for the Cubs. Kwan would obviously be a nice fit for the team. He’s a solid contact hitter for the top of the lineup, plays really good defense, and gets on base at a high level. 

Kwan had another solid all-around season with the Guardians in 2026. He hit .282 with three home runs, 21 doubles, 32 RBI, and 10 stolen bases in 151 games. The lefty outfielder ranked in the 64th percentile in batting run value and the 84th percentile in fielding run value. For context, Happ ranked in the 49th percentile in batting run value and the 81st percentile in fielding run value. 

Kwan would be a slight upgrade over Happ in left field. He won’t hit nearly as many home runs as Happ, but he will strike out less, walk more, get on base more, tally more hits, and play equally strong defense in the outfield. 

Kwan could be a logical trade target for the Cubs in the offseason.