For a franchise that’s walked this tightrope before — balancing short-term wins against long-term dreams — the Chicago Cubs are staring at one of this trade deadline’s most delicate questions:
Should they really deal Owen Caissie?
It’s one thing to trade fringe prospects for a bullpen rental. It’s another when the name in the rumor mill is your No. 1 overall farmhand — a 6-foot-3 Canadian with a left-handed swing built for Wrigley’s wind tunnel and a path to the big leagues that’s looking crowded by the day.
And therein lies the dilemma. Caissie’s not stuck in Iowa because he can’t hit. He’s stuck because there’s no obvious lane to Chicago, as highlighted by Baseball America, who ranked Caissie at No. 2 on its list of top prospects most likely to be traded due to roster circumstances.
Blocked Path to MLB has Cubs Considering Trade of Top Prospect Owen Caissie
With Kyle Tucker in left field, Pete Crow-Armstrong patrolling center, and Ian Happ manning right field, the Cubs have all three outfield spots spoken for — and that’s before mentioning DH Seiya Suzuki, who can also play in the outfield. Of course, the uncertainty surrounding Tucker’s future in Chicago has fans concerned about the potential Caissie-sized hole in the 2026 roster.
Meanwhile, Caissie just keeps producing. He’s batting .269 with 19 home runs and 44 RBIs for Triple-A Iowa this year. He finished the season at Iowa last year with 19 home runs, after clubbing 22 for Double-A Tennessee in 2023.
“I think I’ve developed a lot,” Caissie told MiLB.com this summer. “I feel like I’ve just got to keep doing my thing and wait for the chance.”
So far, the Cubs haven’t shown much appetite for moving him just to plug a short-term hole, even as publications like The Athletic list him among the most likely trade chips to be cashed in before the July 31 deadline. Jon Morosi of MLB Network summed it up thusly:
“I don’t expect Owen Caissie to be traded in a 1 for 1 deal for a rental starting pitcher,” Morosi wrote.
“For Caissie to be moved, return likely would need to include multiple players or a controllable starter.”
Yet the Cubs’ needs are clear. A rotation upgrade would help stabilize a staff that’s wobbled since early June. Another bullpen arm could keep late leads safe. And if the front office wants to stick with this core, they’ll have to pay for it in prospect currency.
Owen Caissie Could Become Latest Cubs Prospect to Emerge Elsewhere
Cubs president of baseball operations Jed Hoyer and GM Carter Hawkins have been keeping their trade cards close to the chest, but Hoyer recently stressed to reporters that, “No one’s untouchable.”
For fans, that means anxiety — and a bit of déjà vu. Cubs history is full of lessons about what happens when you ship off a young stud who hasn’t cracked the big league lineup yet. Caissie’s name now sits in that same conversation that once included Eloy Jiménez, Gleyber Torres and Dylan Cease.
So here we are: a big bat with no clear lane. A team that could absolutely use another frontline arm. And a trade market that loves a lefty slugger with years of club control. It’s not hard to see why Caissie is on every contender’s wish list — or why Chicago keeps showing up on the short list of teams ready to deal.
For now, the power-hitting Canadian remains in Des Moines, waiting for his call — or his ticket elsewhere.
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