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As the 2025 MLB season barrels toward the trade deadline, the Chicago Cubs find themselves in a rare and enviable position: perched atop the NL Central, powered by a revamped roster and the star power of Kyle Tucker. Yet, beneath the surface of their success, cracks have begun to show, particularly in the pitching staff, which has been decimated by injuries, most notably the season-ending loss of ace Justin Steele. With the Cubs in clear “win-now” mode, the front office must make bold moves to shore up their World Series aspirations. That means leveraging assets that, while valuable, are ultimately expendable given the current roster construction and organizational depth.
Why Owen Caissie Is the Cubs’ Most Tradeable Asset
The Cubs’ outfield is locked in for the foreseeable future with Kyle Tucker, Pete Crow-Armstrong, and Ian Happ forming a formidable trio. This leaves top prospect Owen Caissie, who is tearing up Triple-A yet again, without a clear path to regular playing time at Wrigley Field. Caissie, 22, is coming off a stellar 2024 season at Iowa, where he posted an .848 OPS with 19 home runs and 75 RBI. He entered 2025 as Baseball America’s No. 60 overall prospect and has continued to rake, boasting an .862 OPS and 11 extra-base hits in his first 19 games this year.
Despite his promise, Caissie’s value to the Cubs is capped by their current outfield depth. His left-handed power, plate discipline, and youth make him a coveted asset for rebuilding teams, but for Chicago, he represents a surplus. With the Cubs eyeing a deep playoff run and a glaring need for starting pitching, Caissie is the logical centerpiece for a blockbuster trade.
Chicago’s offense, led by Tucker and a resurgent Pete Crow-Armstrong, has been among the league’s best, but the pitching staff has struggled to keep pace. The rotation, already thin after Steele’s injury and Shota Imanaga’s stint on the IL, is relying heavily on overperforming veterans like Matthew Boyd and Colin Rea. The bullpen, too, has been inconsistent, with closer options like Porter Hodge and Ryan Helsley struggling to lock down games.
To sustain their division lead and compete with the NL’s elite in October, the Cubs must add a frontline starter, preferably one with playoff experience and multiple years of control. The market will be competitive, with names like Sandy Alcántara, Tyler Anderson, and Pablo López potentially available. The price for such arms will be steep, but the Cubs’ window is now, and standing pat risks squandering a rare opportunity.
The Trade Proposal
Proposed Trade
Cubs receive:
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Sandy Alcántara (RHP, Miami Marlins)
Marlins receive:
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Owen Caissie (OF, Cubs’ No. 1 prospect)
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James Triantos (INF, Cubs’ top-5 prospect)
This deal is ambitious but realistic for both sides. The Marlins, mired in a rebuild and unlikely to contend in the near future, gain two high-upside position players in Caissie and Triantos, both of whom are close to MLB-ready and could anchor their next core. The inclusion of a young pitcher sweetens the pot and offsets the risk of moving a proven ace.
For the Cubs, Alcántara is the type of workhorse starter who can stabilize a battered rotation and provide a legitimate one-two punch alongside Imanaga (once healthy). He brings a Cy Young pedigree, innings-eating ability, and is under team control through 2026, giving Chicago both immediate impact and future flexibility.
Trading Caissie is not a decision to be made lightly. He is, by all accounts, a future middle-of-the-order bat with All-Star potential. However, championship windows are fleeting, and the Cubs’ current core, Tucker, Swanson, Crow-Armstrong, and Happ, demands aggressive action. The addition of Alcántara not only patches the biggest hole on the roster but also signals to the clubhouse and fanbase that the front office is all-in.
James Triantos, another key piece in the deal, is blocked at second base by Gold Glover Nico Hoerner and at third by a combination of Michael Busch and Matt Shaw. His departure, while painful, is mitigated by the Cubs’ infield depth and the urgency of their current situation.
The Cubs’ recent history is instructive. After years of rebuilding and near misses, they finally have the talent and momentum to make a serious run. But as the 2022 and 2023 seasons proved, even the best-laid plans can be undone by pitching injuries and bullpen meltdowns. The front office’s willingness to move Cody Bellinger and acquire Tucker last winter showed a commitment to bold, decisive action. Trading Caissie for Alcántara is the next logical step.
Owen Caissie is a luxury they can no longer afford to keep in the minors. By flipping him, and a top infield prospect, for a frontline starter like Sandy Alcántara, the Cubs can maximize their championship window. The time to act is now, and Caissie is the player Chicago must trade before the deadline to turn potential into reality.
