Cubs' smartest trade deadline strategy satisfies both Jed Hoyer and Carter Hawkins

While Jed Hoyer has been the one most Chicago Cubs fans credit with the team's cautious approach during the offseason and MLB trade deadline, chances are it's Carter Hawkins who is the biggest influence in that regard. At the very least, after last summer, it's certainly Hawkins who feels comfortable saying that part out loud.

There's no question that overall mindset of the front office has been to find value in any deal they make. There's been exceptions, Alex Bregman signing and Kyle Tucker trade, but for the most part, Hoyer and Hawkins look for deals that not only make the Cubs better now, but also leaves the future intact. In each of those instances, it's likely Hoyer who was the one pushing them across the finish line while Hawkins was pointing to the future risk in each of those moves.

A balancing act between Hoyer and Hawkins may be required at the deadline. Between what the offense has looked like during certain stretches this season, and the idea of the pitching staff getting healthy in September, there's hope that the Cubs could be positioned for an extended run in October.

Even with that hope, it's clear there still be a gap between where the Dodgers are and where the Cubs could be.

Threading needle between 2026 and future could be key to Cubs' 2026 trade deadline

Regardless, it would be negligent of the front office to not add a starting pitcher capable of helping the team this season. That would be the reason why the Tarik Skubal dream remains open, and the Cubs are a strong suitor for Freddy Peralta.

To lesser extent, on the rental side, the Cubs have also been connected to Tyler Mahle. Minimally, there should be an expectation that the rotation will have new addition by the end of the day on Monday.

But, the Cubs shouldn't just stop there. North Side Baseball's Matthew Trueblood reports the Cubs are looking at several controllable pitchers that may need some tweaking. The premise being that one could be a solution for the rotation moving beyond the 2026 season. None of the names mentioned would be a clear answer for what the Cubs need this season, but could speak to a balancing act that is needed between Hoyer and Hawkins before Monday.

Outside of Skubal or someone from the group of Reid Detmers, Jose Soriano, or Emmerson Hancock, the Cubs may need to add two starting pitchers. The first being a rental with the clear goal of ensuring the rotation is stabilized to win in October this season, but also a controllable pitcher that can be plugged in for 2027 and beyond. Balancing Hoyer's measured aggressiveness with Hawkins' cautiousness could ultimately be the key to this deadline.

Add us as a preferred source on Google

Follow