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Chicago Cubs: The 5 prospects most likely to be traded by the deadline

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Chicago Cubs

The Chicago Cubs are expected to be aggressive buyers before the July 31 MLB trade deadline.

With their hold on first place in the NL Central Division shrinking and their weaknesses becoming more glaring as the season heads into the taxing second half, reinforcements are needed for this team with postseason aspirations.

Chicago Cubs needs and wants

Chicago Cubs pitcher Justin Steele (35) pitches against the Arizona Diamondbacks during the first inning at Chase Field.
Mar 27, 2025; Phoenix, Arizona, USA; Chicago Cubs pitcher Justin Steele (35) pitches against the Arizona Diamondbacks during the first inning at Chase Field. Mandatory Credit: Joe Camporeale-Imagn Images

Pitching is needed, of course. Some believe that the Cubs could use two starting pitchers by the deadline to plug the holes left by the injured Justin Steele and Javier Assad. They could also use another left-hander in the bullpen, preferably with swing-and-miss stuff and an ability to occasionally close.

Bench strength is also a need, as there are currently no backups who could step in and sub for an injured or drained starter.

Aggressive in the trade market

Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel.
Jan 12, 2024; Chicago, IL, USA; Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-Imagn Images

With that understood, the Cubs front office has reportedly been all over the place looking for deals, willing to part with top prospects to make them happen

“They’re everywhere right now, and they’re willing to part with [top prospect] Owen Caissie as part of a package,” MLB insider and former GM Jim Bowden recently said on the Foul Territory podcast. “Jed Hoyer and Carter Hawkins literally are everywhere. As I talk to people in the industry, they’re all-in and they’re gonna do what it takes to win.”

Who will most likely be dealt?

Chicago Cubs,owen caissie
Iowa Cubs’ Owen Caissie (17) swings at the ball on Friday, March 28, 2025, at Principal Park in Des Moines.

Here’s a look at the five Cubs assets most likely to be traded before the deadline.

Owen Caissie

The 22-year-old left-handed, power-hitting corner outfielder is currently the Cubs’ no. 1 prospect and is reportedly a desired trade piece for several teams. If the Cubs’ intent is to extend Kyle Tucker, Caissie almost becomes expendable. If they lose Tucker, though, losing Caissie will be felt. The question is whether his promise as a big leaguer trumps a chance at a deep playoff run in the here and now.

Jordan Wicks

The lefty pitcher is attractive trade bait because he’s a young work in progress who’s had a degree of big league success in the past and can immediately be plugged into a rebuilding team’s starting rotation. Since coming back from injury, the 25-year-old has been stellar, with a 1.69 ERA in three starts for the Iowa Cubs. The major league Cubs could decide to hold on to him as a lefty relief option or as a back-of-rotation starter, but he might have more current value as a trade piece.

Jaxon Wiggins

If you follow MLB trade rumors and media trade proposals, you’ll notice that Wiggins’ name pops up a lot. There’s a reason for that. The 23-year-old righty is killing it in Double-A at the moment, sporting a 2.09 ERA in 13 appearances this year. Currently rated the no. 8 prospect in Chicago’s farm system, Wiggins, per MLB.com, projects as a solid mid-rotation starter or a high-leverage reliever.

Kevin Alcantara

If Caissie isn’t traded away at the deadline, many feel that the 22-year-old Alcantara will be the one to go. Alcantara, rated the no. 4 Cubs prospect, is a toolsy player who can confidently play all three outfield positions. Some feel that he’s begun to stagnate a bit as a prospect, but he remains a young asset with a high potential ceiling. On a team in rebuild mode, he could very well be an every day player already.

Ronny Cruz

The 18-year-old Cruz may just be in rookie ball, but he has a very high ceiling and scouts love his raw ability. Currently playing shortstop, the feeling is that he might eventually move on to outfield or third base as his 6-foot-2 frame fills out. The Cubs’ current no. 12 prospect is projected to have 25+ home run power as a big leaguer and has already shown a proficiency for hitting the ball hard.

Things should get very interesting as the trade deadline approaches with the Cubs in full buyer mode and a pennant potentially on the line.


Source: https://www.chicitysports.com/chicago-cubs-5-prospects-likely-to-be-traded?utm_source=rss&utm_medium=rss&utm_campaign=chicago-cubs-5-prospects-likely-to-be-traded


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