And Just Like That, Chicago Cubs Have Left Themselves Scrambling to Catch the Brewers Again

[Matthew Trueblood]

Image courtesy of © Kamil Krzaczynski-Imagn Images

A little over three weeks ago, I made one of my occasional appearances on the excellent Wrigleyville Nation podcast. One thing I said during our conversation on that show was that if Ben Brown made another bulk appearance for the 2025 Cubs, it would mean something had gone horribly wrong. Monday night, they finally felt they could delay the inevitable no longer, and tried Brown again. Not only did they get blown out (thanks especially to Brown getting rocked by the historically inept Royals offense), but the Brewers won their late game, pushing Milwaukee into sole possession of first place for the first time this year.

That was a fitting way for the transfer of power to happen. Ever since a day or two after I made that doomed pronouncement on the podcast, it's been increasingly clear that this would happen—the reemergence of Brown, in the wake of the injury Jameson Taillon suffered during between-starts work the same week of the aforementioned show, and the Brewers catching the Cubs. With Taillon down, keeping Brown away would have had to mean consistently starting Jordan Wicks or Chris Flexen until the team could find some reinforcement for the starting rotation.

What they should have done, of course, was go get that reinforcement right away—and, to give the limited credit due in this case, they did try to do so. The Cubs have been one of the two or three most active teams in the league in terms of trade discussions, sources in front offices throughout the game agree, and that's been true since the beginning of this month—even while other clubs were more focused on the MLB Draft and were somewhat hard to engage. Nonetheless, the team's failure to get anything done reflects two real problems—one very specific, and thus relatively small, for it can't last any longer; and one very general, very big, and very troubling.

The small, specific problem that's almost done being one is the misgiven confidence the organization has had in Brown as a starter. He won the fifth starter job over Colin Rea during spring, when he shouldn't have. He has been given more chances than either his performance or his arsenal merits, and because they were unduly confident in him, they didn't go and reinforce their starting depth in a meaningful way after Javier Assad and Justin Steele (then Shota Imanaga) got hurt early in the season. While the Brewers were making a sagacious little move to pick up Quinn Priester, the Cubs were still rolling loaded, snake-eyed dice on Brown and his two pitches—one of which just isn't very good, except in an aesthetic sense.

Happily, they can't persist in that particular delusion any longer. Brown was farmed out to Iowa with a 6.13 ERA in 16 appearances and almost 80 innings. After a month's reset during which he only pitched in two games, he came back to the majors and watched that number rise to 6.48. His trade value is regrettably shot, but the team will surely wise up and move him to the bullpen (probably with another stint in Iowa to acclimate to that role) or throw him into a trade over the next nine days. It was foolish to have come into this season so ready to give him the ball for extended outings, but that error has become such a searing wound that it will probably cauterize itself.

The much bigger problem, and the one that doesn't appear as easy to fix, is that Jed Hoyer (and, to some extent, the ownership and business operations staff supporting him) is bad at acknowledging when they're in a position of weakness and resigning themselves to making deals without leverage. Hoyer is so value-focused that he misses opportunities to make the team better, not once or twice a year, but six or seven times. We saw the team hold onto Willson Contreras at the 2022 trade deadline, rather than take the best deal they could make for him. We've seen them pull out of multiple trades based on medicals or final details (going all the way back to Hoyer's first offseason in charge, when a trade that would have sent Kris Bryant to the Mets was scrapped at the last second, and coming forward to this past offseason, when two different deals for young starters fell apart). We've seen Hoyer fail to manage upward and gain the flexibility needed to finish contracts for (among others) Alex Bregman and Tanner Scott, and fail in his capacity as a salesman to win over those players on the terms his bosses did authorize.

Never for a moment would the Cubs have considered giving up what the Brewers did for Priester. They didn't have a tradeable draft pick, anyway, but that's not really the point. Milwaukee was in a tough situation, and when they got Priester from the Red Sox, most of the baseball world raised an eyebrow. Especially devoted Brewers fans nearly raised torches and pitchforks; the trade felt like an overpay. Firstly, though, the team badly needed some kind of competent starting pitching help. And secondly, they had chosen their target carefully, and they rapidly finished his development even while running him out every fifth game as a starter. Scouting, player development, and an aggressive, decisive executive netted the team a pitcher who has already given them 95 innings of a 3.33 ERA and is under team control through 2030.

That Hoyer won't overpay, ever, is why the Cubs are in second place, and why they gave the ball to Brown again (behind the thin cover of an opener) on the night when they dropped from the top of the Central. It has to change, and fast, because the Cubs are in a position of weakness now. Nine days from the trade deadline, they're playing from behind, and the team they're chasing is hotter, deeper, and more well-rounded than they are. Chicago needs to make a major upgrade, and yes, Hoyer will have to overpay for it. Whether he has the stomach for that remains to be seen. What happens when he shies away from taking the necessary risks involved in running a winning team, we just saw.

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[TJ11]

Well written.  
the fan boys will not appreciate how realistic this post is.  

[Brock Beauchamp]

4 minutes ago, TJ11 said:

Well written.  
the fan boys will not appreciate how realistic this post is.  

Welcome to NSBB!

[Transmogrified Tiger]

Boy is this really overwrought.  I understand Brown skepticism and don't have strong opinions if they decided on a different starter, but this is pretty conveniently ignoring Brown's MLB proof of concept last season along with his pedigree as reason for optimism.  Also trying to contrast the Cubs' pitching approach as at odds with the Brewers going and getting Quinn Priester is pretty absurd given the bang average output Priester is providing while the Cubs have similarly gotten that from less with the Reas and Flexens of the world this year.  Not to mention that the urgency of the rotation need requiring Brown happened so recently and is likely so short lived that we're talking about a surface area of 2 outings.

 

And then the whole team 'scrambling' and 'position of weakness' nonsense?  The Cubs have the 2nd best record in the NL this month, if the Brewers decide to play at a 162 win pace for the rest of the season there's very little they can do about that.  More likely, they're hitting a local maximum, and while it obviously cuts down on margin for error and makes their upcoming H2H games more important, it doesn't change anything about the team's roster build approach for the deadline and beyond.

[cubfansince77]

Man....where to begin. Trueblood has some VERY good and salient points overall but the fact is this season has been very altered by all the injuries to the starting pitchers. That said, Milwaukee is the better organization from top to bottom right now and if you believe the buck stops at the top then that is on Jed. He's under huge pressure to win and win now. I absolutely believe he's gonna trade most of our top assets to obtain another starter, another reliever or two and a third baseman. It's now or never for him, in that he doesn't have a contract beyond this season. He's a lame duck which doesn't help his leverage in trades either. He's not dealing from a position of strength IMO.

Hope he can pull a rabbit or two outta the hat because with all the other contenders needing pitching it's a crowded market. The sellers have most of the leverage which is evident by the fact he's been trying for some time (by all credible reports) to acquire a starter and the sellers haven't budged in their high demands. Not good overall. 

[UMFan83]

The Cubs came into the season with the following options at starter:  Steele, Imanaga, Taillon, Boyd, Assad, Rea, Brown, Wicks, and Horton.  3 of those players are injured long term, Brown and Wicks haven't worked out in a starter role (I question why both of them have both taken a step back after looking really solid at times last year). Flexen was probably always seen as a long relief guy rather than a starter but I guess he was an option too.

I can't remember if Assad was the favorite for the 5th starter role before he went down but I would have pegged him in at 5, meaning 3 of Cubs projected rotation has missed significant time.  Rea has been better than expected, Horton has had some bumps but has mostly held his own.  You really can't ask for better from your 6th and 7th options.  The issue is Brown/Wicks have not worked out as an 8th option.

Maybe Milwaukee would be fine if they lost 60% of their rotation, their pitching infrastructure makes ours, which I would still consider among the better ones, look amateur.  But the fact is, if your ace misses the entire season, your number 3 misses multiple months and your 5 has missed the entire season so far, most teams are going to struggle with depth.  The good news is the Cubs have the resources to go out and change that.  Jed needs to put on his big boy pants and treat a win now year like a win now year.

 

The other question consideration is, does Craig need to manage with more urgency?  I'm not even saying I agree with this, it's just a question I'm asking.  He's been elite historically at managing his rotation to keep guys sharp through the season so it's hard to question his methods.  But the bullpen game against the Yankees could have been avoided.  The off day on Thursday could avoid another one if they wanted.  Again, I understand why Craig wants to give guys like Boyd and Horton extra rest and it makes complete sense, I'm just saying that a more aggressive manager might be skipping the 5th spot in the rotation when possible.

But the final point is, the Cubs are 28-20 over their last 48 games.  That's a 95 win pace, covering roughly 30% of a season.  No reasonable person would expect to lose 7.5 games in the standings during a stretch like that.  But these questions are coming because the Brewers are playing historically great over that same stretch.  If they played in the AL Central instead of Detroit, no one would be complaining about Jed not building more rotation depth or not being more aggressive about swinging a trade ASAP.  That doesn't make Matt's points invalid, we play in the NL Central so its very valid, just saying that we can't overreact too much or question Jed's entire team building philosophy with a team that is 1 GB the best record in baseball, they just happen to be behind another NL Central team. 

Edited July 22, 2025 by UMFan83

[gflore34]

3 hours ago, Transmogrified Tiger said:

Boy is this really overwrought.  I understand Brown skepticism and don't have strong opinions if they decided on a different starter, but this is pretty conveniently ignoring Brown's MLB proof of concept last season along with his pedigree as reason for optimism.  Also trying to contrast the Cubs' pitching approach as at odds with the Brewers going and getting Quinn Priester is pretty absurd given the bang average output Priester is providing while the Cubs have similarly gotten that from less with the Reas and Flexens of the world this year.  Not to mention that the urgency of the rotation need requiring Brown happened so recently and is likely so short lived that we're talking about a surface area of 2 outings.

 

And then the whole team 'scrambling' and 'position of weakness' nonsense?  The Cubs have the 2nd best record in the NL this month, if the Brewers decide to play at a 162 win pace for the rest of the season there's very little they can do about that.  More likely, they're hitting a local maximum, and while it obviously cuts down on margin for error and makes their upcoming H2H games more important, it doesn't change anything about the team's roster build approach for the deadline and beyond.

Most definitely, and, no mention of what a flawed offensive team the Brewers are, sure, right now they look unbeatable.  They, like the Cubs, have they're warts and they're going to be exposed over the course of a long season.  They've also plenty of arms that, at any moment, could go poof, their bullpen is usage is amongst the highest in baseball.  And, I know they're the Brewers and all but, that doesn't make those bullpen arms immune from tiring down the stretch.

Edited July 22, 2025 by gflore34

[Jeff Alson]

54 minutes ago, UMFan83 said:

The Cubs came into the season with the following options at starter:  Steele, Imanaga, Taillon, Boyd, Assad, Rea, Brown, Wicks, and Horton.  3 of those players are injured long term, Brown and Wicks haven't worked out in a starter role (I question why both of them have both taken a step back after looking really solid at times last year). Flexen was probably always seen as a long relief guy rather than a starter but I guess he was an option too.

I can't remember if Assad was the favorite for the 5th starter role before he went down but I would have pegged him in at 5, meaning 3 of Cubs projected rotation has missed significant time.  Rea has been better than expected, Horton has had some bumps but has mostly held his own.  You really can't ask for better from your 6th and 7th options.  The issue is Brown/Wicks have not worked out as an 8th option.

Maybe Milwaukee would be fine if they lost 60% of their rotation, their pitching infrastructure makes ours, which I would still consider among the better ones, look amateur.  But the fact is, if your ace misses the entire season, your number 3 misses multiple months and your 5 has missed the entire season so far, most teams are going to struggle with depth.  The good news is the Cubs have the resources to go out and change that.  Jed needs to put on his big boy pants and treat a win now year like a win now year.

 

The other question consideration is, does Craig need to manage with more urgency?  I'm not even saying I agree with this, it's just a question I'm asking.  He's been elite historically at managing his rotation to keep guys sharp through the season so it's hard to question his methods.  But the bullpen game against the Yankees could have been avoided.  The off day on Thursday could avoid another one if they wanted.  Again, I understand why Craig wants to give guys like Boyd and Horton extra rest and it makes complete sense, I'm just saying that a more aggressive manager might be skipping the 5th spot in the rotation when possible.

But the final point is, the Cubs are 28-20 over their last 48 games.  That's a 95 win pace, covering roughly 30% of a season.  No reasonable person would expect to lose 7.5 games in the standings during a stretch like that.  But these questions are coming because the Brewers are playing historically great over that same stretch.  If they played in the AL Central instead of Detroit, no one would be complaining about Jed not building more rotation depth or not being more aggressive about swinging a trade ASAP.  That doesn't make Matt's points invalid, we play in the NL Central so its very valid, just saying that we can't overreact too much or question Jed's entire team building philosophy with a team that is 1 GB the best record in baseball, they just happen to be behind another NL Central team. 

I completely agree.

The Cubs have a .590 winning percentage, ahead of the Dodgers and Phillies and one game worse than the best record in baseball, and have playoff odds of over 90%. Who would have not taken that in spring training? Jed made two incredible starting pitching signings with Boyd and Rea. To criticize him for not anticipating injuries to 4 of the 5 incumbent starting pitchers, and not investing more in the #8 and 9 starters, simply because we are one game behind a team that is playing .600 ball, is ridiculous.

I, for one, hope they don't overpay for a #4 or #5 starter who will be of little value in the playoffs. If they are going to overpay, my favorite target would be Suarez, moving Shaw to a utility role, or a top reliever, as both would add more value in the playoffs than a #4 or 5 starter.

[Connor McConnor]

Milwaukee has been ridiculous in the last 6 weeks, and we have played well.  St. Louis is buried (knock knock).  The current standings have very little to do with the Cubs and everything to do with the run the Brewers have had.   If they (Brew) continue playing the way they have, they deserve to win the division.   That is highly unlikely.  We have survived minus 3 of our starters.  Let's get some reinforcements and see what happens.  I like our chances.

[PVG]

Isn't the real question : The Brewers payroll is about 100 Million and the Cubs' is double that - so how come the brewers are so good every year?