A critical Cubs trade deadline misstep could haunt them for years to come

The Chicago Cubs made it a series in Milwaukee after dropping Games 1 and 2, yet they couldn't complete the comeback. After roaring to life at Wrigley Field and gaining the momentum heading into last weekend's Game 5, the offense, as had happened all too often in the second half, fell flat against a crew that included a razor-sharp Jacob Misiorowski and Chad Patrick.

The offense's second-half vanishing act can't entirely be blamed on management or even the front office. Jed Hoyer traded for Kyle Tucker to be a consistent game-changer, and yet he endured the worst slump of his career and had been a non-factor for most of October alongside their budding superstar, Pete Crow-Armstrong. They led a group that had a 115 wRC+ and ranked third among all teams in hitting in the first half. On the pitching end, Cade Horton's late injury after a Jake Arrieta-like run will also be a haunting what-if scenario.

Where there remains a bit of second-guessing is the trade deadline. The loss of Justin Steele and Javier Assad early in the season and injuries to Shota Imanaga and Jameson Taillon throughout the year made adding a starting pitcher appear obvious to everyone. They specifically left plenty of financial wiggle room in the offseason, after salary-dumping Cody Bellinger and not pursuing Alex Bregman aggressively, to fill such needs mid-season. Moreover, a blockbuster trade for one year of Tucker and a bunch of players, namely PCA, exceeding expectations early on, framed this as a year to really go for it.

Instead, the closest they got was Michael Soroka, a massive risk given his sudden decline in velocity in Washington, and one that immediately backfired with an IL stint of his own. They never came close to fully deploying that remaining war chest. In the end, they got what they paid for, with both Imanaga and Matthew Boyd running out of gas and throwing clunkers that dug an 0-2 hole for the Cubs in the NLDS.

The lack of aggression from a team with prospects like Owen Caissie and Kevin Alcantara to offer, and a prime opportunity to capitalize on a stellar first half, was puzzling. In fairness to Hoyer, an ace wasn't in the cards. Asks for guys like MacKenzie Gore or Joe Ryan were starting at Horton and Matt Shaw. That was, understandably, a non-starter, and those non-deals only look better with age. The same goes for most of the middle-to-back-end options, too, like Charlie Morton (6.75 ERA in the second half) and Adrian Houser (4.81 ERA). What hurts is that they never pivoted their strategy to land impact elsewhere.

Andrew Kittredge brought them plenty of value with a 3.38 ERA while helping close out their first postseason series win since 2017, and Willi Castro, for all his struggles, still was able to provide some much-needed rest for key Cubs players. Those aren't moves to rally around, though. They could've focused on reinforcing the bullpen to cover for questionable starting pitching. Jhoan Duran, who cost the Phillies #92 prospect Mick Abel and #56 prospect Eduardo Tait, remained lights-out down the stretch and won't be a free agent until 2028, for instance. No single trade stands out as the right answer in the backdrop of an offensive collapse, but it always felt wrong not to be ambitious.

The Cubs' competitive window requires serious effort to keep open

With a potential landscape-changing lockout looming in 2027 and Ian Happ, Nico Hoerner, Seiya Suzuki, Taillon, Boyd, and others hitting free agency that year, the Cubs will now have to capitalize before this group potentially scatters into the wind. They aren't going to tie a bunch of money up in one player, but there are more ways than one to improve this roster. Even if Tucker is almost a lock to sign elsewhere, there is a deep starting pitching market to explore and potential trades to revisit, like for Sandy Alcantara or Ryan. They have to start acting like a team with championship ambitions, though.

The Cubs do have the skeleton of a good, if flawed, unit in place for the long haul, between PCA, Horton, Michael Busch, Moises Ballesteros, Matt Shaw, Dansby Swanson, and Daniel Palencia. Caissie, Alcantara, and Jaxon Wiggins are also waiting in the wings. However, 2025 was a rare opportunity to take advantage of something Hoyer has espoused in his time as president — exceeding expectations. This trade deadline did not meet that moment, and it may come to haunt them if their efforts this offseason don't translate into the same level of success. For as good as this season was, it still felt like something was left on the table.