Iowa Cubs' Owen Caissie (17) swings at the ball on Friday, March 28, 2025, at Principal Park in Des Moines. Cody Scanlan/The Register / USA TODAY NETWORK via Imagn Images

Cubs Willing To Deal Top Prospect at Trade Deadline, MLB Insider Says

Originally posted on Chicago Cubs on SI
By Michael Brauner | Last updated Jul 2, 2025 12:00 PM ET

The Chicago Cubs are expected to be one of the most aggressive teams in trying to make upgrades at this month's trade deadline.

With the calendar now turning to July, things have gotten very real and difficult decisions are going to have to be made if the Cubs want to put themselves in a position to contend.

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Chicago is certainly capable enough -- provided they make the right upgrades -- to at the very least compete for a National League pennant, and their run over the first half proved it.

Now that they have cooled off though and are clinging to a slim divisional lead, the need to shake some things up has become very clear.

During an appearance on Foul Territory, former MLB general manager and current insider for The Athletic Jim Bowden spoke about the team's aggression to get something big done and even revealed their willingness to deal their top prospect.

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The Cubs are going to win the trade deadline in the NL Central, says @JimBowdenGM.

"As I talk to people in the industry, they're all-in." pic.twitter.com/h7cfaGTWJw
— Foul Territory (@FoulTerritoryTV) June 30, 2025

"They're everywhere right now, and they're willing to part with [top prospect] Owen Caissie as part of a package," Bowden said. "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."

The Cubs entertaining trading Caissie is not a massive shock especially for some of the names they have been linked to. However for Bowden to be so definitive and state the team's willingness to deal away their highest-rated prospect is fascinating.

A 22-year-old outfielder, Caissie has slashed .263/.372/.504 this season with 12 home runs and 33 RBI in 65 games.

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Caissie is now a seasoned Triple-A veteran who has played nearly 200 games there and could be ready for the next step, but Chicago does not have a spot for him.

The obvious concern with trading him is the thought that if they fail to re-sign Kyle Tucker, Caissie is the logical next one in line.

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However, you don't make a move like the one the Cubs made for Tucker only to no go all-in on trying to win in the potentially very short window he is here.

Chicago wants to keep Tucker long-term and cannot hesitate to make a trade now on the chance they are too cheap to retain him down the line.

Caissie should be extremely valuable in any potential trade that sees the Cubs fix their weaknesses, and while it would sting to part ways with another potential future star, what would sting a lot more is not capitalizing on a championship window that is very clearly open right now.

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This article first appeared on Chicago Cubs on SI and was syndicated with permission.

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