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The Chicago Cubs are back. With the All-Star break around the corner, this franchise has proven itself to be a legitimate contender once again. It took longer than the North Side had hoped, but authentic enthusiasm is flowing through Wrigley Field. The Cubbies (55-38) are only a half-game behind the Los Angeles Dodgers for first place in the National League. However, they are also only two games clear of the Milwaukee Brewers in the NL Central.
Longtime general manager Jed Hoyer must do his best to position Chicago for a World Series run. The July 31 trade deadline affords him that opportunity, but it could come at a significant cost. One name repeatedly keeps coming up in trade talks, and unsurprisingly, he happens to be the team's top prospect. Potential sellers have their eye on premier slugger Owen Caissie.
“In most organizations, he’d be in the big leagues right now,” MLB Network's Jon Morosi posted on X. “But the Cubs have {Ian Happ}, {Pete Crow-Armstrong}, {Kyle Tucker}, and {Seiya Suzuki}. In virtually every Cubs trade conversation, the rival GM will ask about him.”
Caissie, who is currently slotted as the No. 43 prospect in MLB, is conquering pitchers in Triple-A Iowa right now. He has three multi-home run games since July 3 and has 19 overall. The 23-year-old outfielder is also batting .278 with a .575 slugging percentage and .961 OPS. Keeping him in the minor leagues is becoming harder to justify by the day. But where is his opening in Chicago?
Owen Caissie's path to Wrigley is not clear-cut
Like Morosi notes, the Cubs have a crowded outfield. Crow-Armstrong has quickly bloomed into a history-making MVP candidate in center. Tucker's arrival has helped facilitate the club's momentous breakthrough in 2025. Although he will be a free agent, ownership is reportedly interested in making a long-term commitment. The obvious player to swap out is Happ, as he is batting just .224 with a sub-.700 OPS this season, but the 30-year-old left fielder is a three-time Gold Glover, has a no-trade clause and is signed through 2026.
The Cubs are in a bind. While it is true that an outfield logjam is a first-world problem, the front office is incentivized to go all in at the deadline and solidify Chicago's championship ambitions. That added sense of urgency makes it more practical to deal away someone who has never recorded an MLB at-bat, even if he is prodigiously talented. But here is where another issue arises. There does not seem to be an available star who warrants such a sacrifice.
What does the trade market look like for Cubs?
If Hoyer is going to ship out a prized prospect Owen Caissie, he better net a massive fish in return. There is no indisputable trout swimming in the trade market at this current time. The Cubs' desire to add another starting pitcher is well known, but is there an actual ace who is attainable this year?
Despite occupying that role in the past, 2022 Cy Young Award winner Sandy Alcantara presently has a ghastly 7.22 ERA. Zac Gallen is an intriguing choice after posting two stellar starts in a row, but he still has an ERA that exceeds 5.00 and an expiring contract. Joe Ryan and Mitch Keller are not worth Caissie, either, even though they are both locked up for the next several years and under the age of 30.
Reasonably speaking, Chicago could acquire any one of those hurlers without parting with its most valuable asset. It would be easy to solve this future outfield dilemma at the end of July, using a Fall Classic pursuit as justification for the mega move. But a golden opportunity is not an excuse for recklessness.
Jed Hoyer and company will need to look for the right trade partner if they are intent on dealing Owen Caissie. And that may mean waiting to revisit this situation in the winter. Although the Cubs are not historically a franchise that gets to have their cake and eat it too, perhaps they could figure out a way to simultaneously contend in the present and preserve the future.
