For more than a month, insiders throughout the league boldly proclaimed that the Chicago Cubs would be among the busiest teams in the league leading up to the trade deadline - and it was clear what this team needed above all else: a top-end starting pitcher.
But instead of pushing the chips in on the one season we know Kyle Tucker will be here, Jed Hoyer did what he does best and played things conservative, with the team's only rotation depth coming in the form of oft-injured right-hander Michael Soroka. So, here we are, strapping ourselves in for the stretch run, hoping and praying this Cubs roster has enough to overcome Milwaukee and make a run come October.
Before we look ahead, let's go through three takeaways from, frankly, what amounts to an infuriating trade deadline.
3 important takeaways from the Cubs' trade deadline moves
1: Whether they admit it or not, the Cubs are planning on losing Kyle Tucker
In a post-deadline appearance on 670 The Score, Hoyer was pressed on whether or not holding onto Owen Caissie had anything to do with the fact that Kyle Tucker will be a free agent at year's end. A free agent who, by most estimates, is looking at a $400+ million payday - well outside the scope of anything the Cubs have ever offered anyone.
Kyle Tucker's uncertain future was “somewhat connected” in how the Cubs handled Owen Caissie in trade talks, Jed Hoyer says.
— 670 The Score (@670TheScore) August 1, 2025
Hoyer also emphasizes the two can fit together.
"He can also be part of a bright future that involves Kyle Tucker as well," Hoyer says of Caissie. pic.twitter.com/liTsua3jui
Hoyer acknowledged not including top prospect Owen Caissie in a blockbuster was 'somewhat connected' to the uncertainty with Tucker, but said there's a future where both could be on the team long-term. That's laughable to think, given Pete Crow-Armstrong has center field locked down and the team has both Ian Happ and Seiya Suzuki under team control through next year, but here we are.
The Cubs are safeguarding against what feels inevitable: Kyle Tucker will depart in the offseason with his big bag of money, and Chicago will turn to a highly touted, yet unproven prospect in hopes he can step in and fill the shoes of a four-time All-Star.
2: As a fanbase, we are being repeatedly lied to by the front office and ownership
Remember when Jed Hoyer unloaded Cody Bellinger in a straight salary dump and the rest of the offseason, the Cubs played it safe and failed to reinvest that money? But we were told that it could allow for increased flexibility for in-season additions at the trade deadline?
We're beyond a shadow of a doubt now. Those savings went straight to the bottom line, and the Cubs have failed spectacularly in re-investing the $20 million that came off the books in that trade. It's just indicative of a larger problem: this is an owner who refuses to prop up a payroll commensurate with either the revenue he's pulling in or the ever-increasing value of the franchise.
Every year, things get more expensive at Wrigley Field and another Wrigleyville development project takes shape. And every year, we're fed the same schtick about building a sustainable winner, finding value around the margins and not getting bogged down on huge financial commitments. That small market line of thinking might get you to October - but puts you at a major disadvantage come the postseason.
3: The Cubs feel very confident in the imminent returns of injured pitchers
You cannot, in any universe, look me in the eye today and tell me that Michael Soroka is ready to start a postseason game for the Chicago Cubs. Well, he might start it, but starting it and giving the chance to win said game are two wildly different things.
I wrote about the trade when it went down on Wednesday. I like the move and think the Cubs' defense could work wonders for him, pushing his performance closer to his expected metrics. But there's no way I'm comfortable saying he's going to be the guy behind Matthew Boyd and Shota Imanaga in a best-of-five.
The fact that the Cubs came up short in every other effort to add starting pitching on Thursday tells me they have a ton of confidence in the returns of Javier Assad and Jameson Taillon and what that will mean to the team down the stretch. They're so confident, in fact, they're apparently willing to bet the end result of their one season with Tucker on it. Let's hope they're right or, otherwise, this already bad-looking deadline could look even worse this fall.
