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Urgent Times Call For Bold moves; Chicago Cubs Poised to Trade Four Top Prospects in Aggressive Push at MLB Deadline

Richard Jefferson
June 16, 2025
2 Min Read

The Chicago Cubs are going to be buyers at this year’s trade deadline, which means some top prospects could become trade chips soon

The Chicago Cubs are off to a strong start this season and are firmly in the World Series contender mix.

With their championship window possibly limited by Kyle Tucker’s contract situation, the Cubs are expected to be aggressive at the trade deadline in pursuit of top-tier talent.

That likely means dipping into their deep pool of prospects—putting certain players in the spotlight as prime trade candidates.

Owen Caissie

Player Profile: Owen Caissie - Inside The Diamonds

Drafted in the second round in 2020 as one of the youngest players in his class, Caissie has spent several years developing in the Cubs’ system. Though he appears close to MLB-ready, there’s limited room for him on the current roster.

Ranked as MLB Pipeline’s No. 46 overall prospect, Caissie holds significant trade value and could be a key piece in a deal, likely one that brings back an elite player in return.

James Triantos

James Triantos is the prospect that Chicago Cubs fans need to keep an eye on

While Triantos has taken a slight step back at Triple-A this season, he’s still regarded as one of the Cubs’ top prospects. Primarily known for his defense, he also brings speed to the table, having stolen 47 bases last year. Despite a modest .250/.304/.313 slash line, his trade value likely remains intact. With Nico Hoerner already filling a similar role at the MLB level, the Cubs might consider exploring trade options for Triantos.

Kevin Alcántara

Cubs call up prospect Kevin Alcántara

Alcántara is nearing MLB readiness and boasts massive upside as a center fielder, with a rare combination of size (6’6″) and athleticism that gives him 20/20 potential. However, with Pete Crow-Armstrong emerging as the likely long-term answer in center for the Cubs, Alcántara could be a prime trade chip whose value should be maximized now rather than left to stagnate in Triple-A.

Jack Neely

Jack Neely's Debut Was a Bit of a Mess, But I Don't Think Anyone is All That Discouraged - Bleacher Nation

Unlike the others, Neely isn’t a top-tier prospect but could be useful as a bullpen arm. He’s racked up strikeouts in the minors but has recently struggled with control—an issue that’s new and not yet overly concerning. Acquired from the Yankees in the Mark Leiter Jr. deal, the 25-year-old could be flipped again as part of a trade package.

Last Update: June 22, 2025

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