What’s up, everybody? It’s the Chi Kid here, and we need to have a real conversation about the Chicago Cubs and their absolute refusal to play big-boy baseball when it comes to free agency.
Let’s get straight to it—Alex Bregman signed a four-year, $120 million deal with the Boston Red Sox, and the Cubs weren’t even a serious player in the mix. Look, I get it. $40 million AAV is wild for a guy in his 30s, and Bregman could very well opt out after a year if he has a monster season. But what’s new? The Cubs were, yet again, just sitting there watching other teams make moves.
The Matt Shaw Problem
Now, the front office wants us to believe in the farm system. Cool. But then we wake up to news that Matt Shaw—our No. 19 overall prospect and the supposed future at third base—has an oblique injury. And if history has taught us anything, oblique injuries aren’t just “day-to-day.” They can turn into weeks, if not months (ask Seiya Suzuki).
So now, not only did we not sign a legit third baseman, but we also don’t have a real backup plan outside of John Berti or Nikki Lopez. That’s it. That’s our depth. We’re supposed to just cross our fingers and pray this injury doesn’t linger all season.
The Cubs’ Never-Ending Excuses
I have to be consistent. I can’t sit here and say I wanted the Cubs to go all in on Chris Bryant back in 2014-15, and then turn around and say I don’t want them to take the same approach with a guy like Bregman or any other major free agent.
The Cubs keep acting like they’re broke. They’re still paying deferred money to Jon Lester and Jason Heyward, and apparently, that’s the reason why we can’t spend money today? Give me a break. Those guys won us a World Series. That’s the price of winning. You don’t stop spending just because you’re still selling 2016 championship merch.
“We Made a Strong Offer”—Enough Already
I am so sick of hearing about “strong offers.” If I fail a test and tell my mom, “Hey, I tried really hard,” do you think she’s going to be happy about that? No. She doesn’t give a damn.
Jed Hoyer has been out here making “strong offers” for every major free agent since 2018. And who have we actually signed? Nobody.
- Bryce Harper? Strong offer.
- Manny Machado? Strong offer.
- Mike Trout? Strong offer.
- Shohei Ohtani? Strong offer.
- Carlos Correa? Strong offer.
- Yamamoto? Strong offer.
- Pete Alonso? Strong offer.
- Bregman? Strong offer.
At some point, we have to start asking: Are we even trying to win? Because the Dodgers make strong offers too—but they actually get the deals done.
What Needs to Change?
The Cubs are not a small-market team. Chicago sells itself. Wrigley Field sells itself. The Cubs should be a major player in free agency every single year. But as long as Tom Ricketts refuses to spend, and as long as Jed Hoyer keeps playing it safe, we’re going to be stuck in this perpetual cycle of mediocrity.
The Cubs have one of the best farm systems in baseball right now. Cool. But imagine if they actually paired that with a real free-agent signing. Imagine adding Bregman or Pete Alonso to a lineup that already has Kyle Tucker. How quickly do the Cubs become the favorites to win the NL Central? But instead, we’re sitting here talking about how we “almost” landed a star player—again.
The Reality of 2025
I love Kyle Tucker in a Cubs uniform. I think he’s going to have a career year—35 homers, 105 RBIs, batting .285-.290. But if the Cubs let him walk after just one season, what was the point?
If I’m still rocking a Patrick Wisdom jersey in July because I’m too afraid to buy a Cubs star player’s jersey (since they all end up leaving), then what are we even doing?
It’s time to stop talking about making strong offers and actually start winning again. I’ll believe it when I see it. Until then, I’ll be watching the Cubs let another top free agent slip away next offseason.
Peace.
