The Chicago Cubs are at a pivotal point in not only this 2025 season, but in their chances of success in the following years.
For that reason, their movements before the July 31 trade deadline will be especially important.
Some are saying that Cubs president of baseball operations Jed Hoyer is a victim of his own success. Compelled by the need to make the playoffs for the first time in his reign as top exec and by his own expiring contract (two intertwined pressures), he built a team that has the grit, gumption, defense, and offensive prowess to be a World Series-viable team when the goal for this year was, maybe, just to make a postseason-viable team.
Chicago Cubs: Ahead of the curve, against the wall
What this means is that this 2025 product wasn’t meant to be the fully-actualized Cubs/Hoyer product just yet. It was meant to be the 2015 learning-curve campaign that seasoned the crew before the 2016 World Series victory.
But this year’s squad has been so good and has bubbled over with so much magical winner’s chemistry that there’s now a palpable pressure to skip the learning curve and jump right to the World Series.
Realistically, though, the Cubs are lacking some key pieces to make that jump.
And that’s why there’s so much pressure focused on Chicago’s moves prior to the trade deadline.
Starting pitching woes
The starting rotation, specifically, is a major concern. As it stands now, Shota Imanaga is at the top, one start into his return from hamstring injury. Below him is Matthew Boyd, who has pitched extremely well, but who also has an extensive history of injury and hasn’t logged over 100 innings pitched since 2019. Then there’s Jameson Taillon, who has pitched solidly at times, but has recently been swatted around.
Beyond that, the starting corps is all crossed fingers and wishful thinking with rookie Cade Horton and veteran swing man Colin Rea currently manning back-of-rotation duties– and taking on water while trying. Wildly inconsistent sophomore Ben Brown has been sent to Triple-A alongside once-upon-a-time rotation hopeful Jordan Wicks, who is returning from injury. Then, there’s projected fifth starter Javier Assad, who’s been battling an oblique issue all season and has yet to throw one competitive big league pitch this year.
This spells big trouble if the 2025 Cubs want to have a serious shot at going deep into the postseason. It could even be argued that they’re one starting pitching injury away from possibly being out of the playoff picture entirely
More than just one rental pitcher away
Lindsey Willhite of Deadspin recently opined that the team will need to target two quality starters prior to the deadline to have a serious shot at doing something big this postseason.
Per Willhite:
“To solve this shortcoming, Cubs GM Jed Hoyer and his cabinet need to be even bolder than they were when they acquired [Kyle] Tucker in the offseason.
They have maneuvered themselves into a place where they’re closer to the Dodgers and Mets than they could have realistically projected. But if they’re going to wait to be equals before they strike, then they might as well sell the team.
The Dodgers, with their billions of dollars and their brilliant front office, are never going away. Mets owner Steve Cohen’s wallet will be wide open every offseason and every trade deadline.
That means now’s the time to peel a prospect or five off their thick stack of youngsters and acquire two legitimate starters — guys who can get the Cubs through five innings in an October setting.
And don’t just focus on the rentals.”
Willhite mentions checking in on Tanner Bibee of the Cleveland Guardians, Nathan Eovaldi of the Texas Rangers, and Mitch Keller of the Pittsburgh Pirates, among others. All of them under contract beyond 2025.
The strategy is clear, though. And it’s not incorrect.
Picking up two high-end starters would turn this Cubs team into a real big-prize contender and not just a feel-good fairy tale hopeful. But to add two high-end starters who are team controlled beyond this season would provide a huge boost to the franchise over the next several years. That’s why the idea of a trade with the Miami Marlins for Sandy Alcantara or Edward Cabrera has gotten so much attention.
But would it be worth emptying out their farm system to pull the trigger on two major pitching acquisitions? That’s the question Jed Hoyer must ponder.
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