After my piece last week on Tatsuya Imai signing with the Astros, it only seems fair to revisit the narrative a bit. Early on, it was easy to paint the Cubs’ front office as cheapskates, but many sources have made clear the real sticking point was contract structure, not cash, with Houston ultimately giving Imai a three-year deal that includes player opt-outs after each of the first two seasons while Chicago pushed for more team control over all three years — a stance that makes a lot more sense when you remember Shota Imanaga will become a free agent after the 2026 season. With that context in mind, the Cubs’ latest move to address their rotation — acquiring hard-throwing right-hander Edward Cabrera from the Miami Marlins in a trade that sent shockwaves through baseball’s prospect rankings — looks less like penny-pinching and more like a front office choosing where, and on whom, it is willing to take on risk.
What makes this trade particularly noteworthy is the centerpiece heading to Miami; Owen Caissie who was the Cubs’ top outfield prospect. Caissie was rated as the Cubs’ No. 1 prospect and ranked No. 47 overall by MLB Pipeline. The 23-year-old Canadian outfielder has long been viewed as one of the organization’s most exciting pieces, possessing the kind of elite power potential that teams spend years developing in their farm systems. In 505 minor league games since 2021, Caissie has slashed .280/.384/.487 with 120 doubles, nine triples, and 81 home runs, making him the type of prospect teams typically hold onto at all costs.
Alongside Caissie, the Cubs also dealt away infield prospects Cristian Hernandez and Edgardo De Leon to complete the package. Hernandez, who just turned 22, was the Cubs’ No. 11 prospect and represented another high-ceiling young talent with legitimate tools at multiple infield positions. De Leon, an 18-year-old corner infielder and outfielder, rounds out the three-player return for Miami, giving the Marlins what amounts to an organization-altering haul of young talent.
The timing of this deal is particularly interesting when you consider the history between these two organizations. The Cubs and Marlins had been discussing Cabrera for well over a year according to many reporters. The two clubs had even explored acquiring Cabrera ahead of last summer’s trade deadline when Chicago was searching for rotation help. Those conversations never materialized into a deal at that time, but the Cubs’ front office clearly remained interested in the Marlins’ young hurler. This trade represents the culmination of months — if not longer — of negotiations between the organizations about what it would take to finally get a deal done.
Cabrera is coming off the best season of his career, which made acquiring him attractive enough to justify the prospect capital. The 27-year-old right-hander posted a 3.53 ERA in 2025 with career highs in starts (26), innings pitched (137⅔), and strikeouts (150). During one particularly impressive stretch from May 4 through August 8, Cabrera ranked third in the National League in ERA at 2.22, trailing only Cy Young Award winner Paul Skenes and finalist Cristopher Sánchez. For a Cubs organization that has been searching for consistent, quality starting pitching, that kind of performance is exactly what they’ve been lacking.
The elephant in the room with Cabrera, however, is his injury history. Throughout his career with the Marlins, the hard thrower has dealt with various elbow and shoulder issues that have limited his availability. Even in his excellent 2025 season, he wasn’t immune to scares — he dealt with posterior right elbow discomfort in July and exited a start with right elbow sprain in late August. Despite these setbacks, Cabrera managed to stay healthy enough to make quality starts down the stretch, including a five-inning shutout performance on September 28 that helped eliminate the Mets from postseason contention.
From a financial perspective, the trade also makes sense for the Cubs, who have been strategic about how they allocate resources this offseason. Cabrera remains under team control through the 2028 season, meaning the Cubs won’t be competing for him in free agency against teams with deeper pockets. His arbitration salary for 2026 figures to be a reasonable figure compared to what the Cubs would have paid for a rental or a free-agent starter in today’s market.
The Cubs’ front office, led by president of baseball operations Jed Hoyer, made it clear this winter that the team was in the market for both rotation and bullpen help. The rotation has been decimated by injuries, and heading into 2026, the uncertainty around Justin Steele’s return from elbow surgery made adding another arm even more critical. Cabrera’s electric arsenal — headlined by a 94.2 mph changeup that’s considered one of his best pitches — gives the Cubs a different dynamic on the mound that some of their other starters don’t provide.
Here’s the thing, folks: The Cubs are losing in Caissie and the decision to deal away your top prospect is never easy, even when you’re getting a proven pitcher in return. The young outfielder had made his MLB debut last August but was limited by a concussion that ended his season early. Still, his minor league resume speaks for itself, and he was expected to compete for an Opening Day roster spot with the Cubs this spring. However, given the organization’s immediate need for pitching and the relatively tenuous run-scoring projections for 2026, the front office apparently felt that addressing the rotation took priority.
With that… This trade fundamentally shifts the Cubs’ direction heading into spring training and beyond. By mortgaging future outfield depth for immediate rotation help, the team has made a clear statement about its 2026 window and its confidence in being able to compete now. Whether that gamble pays off will ultimately depend on whether Cabrera can stay healthy and continue producing at the level he showed in 2025, and whether the Cubs can compensate for losing one of their most promising young bats by adding offense through free agency or other means.
If you cannot play with them, then root for them!