Should Brewers' Transcendence Prompt a Bigger Swing from Cubs at MLB Trade Deadline?

[Matthew Trueblood]

Image courtesy of © Michael McLoone-Imagn Images

Just before Opening Day, I projected that the Cubs would win the 2025 NL Central, with 89 wins. I had the Brewers just one small step behind, at 88-74. At multiple points over the first half of the season, I made note of the fact that despite what appeared to be trends away from that projection, it still felt right to me. Now, a day before the MLB trade deadline and roughly two-thirds of the way through the season, the Cubs could go roughly .500 from here and finish with exactly that 89-73 record. I feel like I largely got them right this year. 

Justin Steele's injury was a major setback, but not a wholly unexpected one. Pete Crow-Armstrong's season has been a wonderful surprise, but there have been some oft-overlooked warts lurking there all along, and indeed, Crow-Armstrong has a .284 OBP in his last 40 games and is starting to have lapses in the field and on the bases. Many things have varied from any specific expectation, but they've averaged out, and looking forward, I see a team that will need to fight hard to get to 90 wins. That's fine; 90 wins was a reasonable goal for this season and will certainly get them into October, if they get there.

What I had wrong was the Brewers. Their unexpected performances haven't evened out, and they're not going to. Between Isaac Collins, Jacob Misiorowski, Quinn Priester and Andrew Vaughn, Milwaukee is legitimately five or six wins better than I had projected in March. I expect them to win 94 games or so, which means that the Cubs have to keep the pedal down in order to keep pace—or resign themselves to playing in a Wild Card Series somewhere just after the end of the regular season, at best.

Should that alter Jed Hoyer's approach over the next 29 hours or so? It's a bit hard to say. The Cubs extended the contract of their president of baseball operations earlier this week, in a head-scratching, cart-before-the-division-title move. Presumably, that wasn't a move designed to take pressure off Hoyer, so much as to redistribute that pressure in a healthier way throughout the organization. Either way, though, Hoyer now has job security. He faces the dilemma, therefore, of whether to trade from the long-term depth of the organization to make this team better by a significant enough margin to give them a real chance to beat out the Brewers over the final two months.

It's been hard to feel good about the (no pun intended) prospects of going all-in over the last two nights. The Cubs didn't just lose to the Brewers; they got righteously whupped. None of the main candidates identified as their top trade targets would have materially changed what happened over the last two games; they were beaten by wide margins and in all facets. It doesn't feel like marginal upgrades will close the lacuna between the clubs.

Feelings be damned, though, the Brewers will cool off at least slightly, sometime between now and the end of September. When they do, the Cubs have to be able to pounce, as Milwaukee has pounced by racing past the limping, .500ish Cubs over the last month and change. Right now, the Cubs roster lacks the depth and the dynamism to do that. They need better pitchers at the back end of their starting rotation and in middle relief. They need better bench options, to give their regular position players some needed rest and put the danger back in those bats, the lift back in their step. If Hoyer doesn't acquire multiple players with real and immediately visible utility to this roster by Thursday evening, his team will founder and fumfer their way to a quick October ouster—or worse.

That won't necessarily mean the team failed. They're probably going to hit that 89-win benchmark I set for them four months ago; they might yet exceed it. It'll just mean they were overwhelmed by a team on a mission, doing things better than them. Since the Brewers are set up better for the future than are the Cubs, though, that would be extremely cold comfort. To get the Cubs out of the quagmire they've been stuck in since before he took over the job, Hoyer needs to get his arms extended and hit a home run at this trade deadline. Whether he even has the pop in his bat to do that when he barrels one up is not clear.

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[gflore34]

"What I had wrong was the Brewers. Their unexpected performances haven't evened out, and they're not going to."  - so this only true for the Cubs?   Vaughn, for example, by all metrics and sample size is a bad player yet, somehow, because he's in a Brewers uniform he won't regress when all meaningful data suggests otherwise?

[Outshined_One]

[squally1313]

1 hour ago, Matthew Trueblood said:

Pete Crow-Armstrong's season has been a wonderful surprise, but there have been some oft-overlooked warts lurking there all along, and indeed, Crow-Armstrong has a .284 OBP in his last 40 games and is starting to have lapses in the field and on the bases.

PCA's last 40 games date back to 6/9 (nice). Over that stretch he has a 127 wRC and the 12th most fWAR in baseball. Those warts are really coming out!

 

1 hour ago, Matthew Trueblood said:

Milwaukee has pounced by racing past the limping, .500ish Cubs over the last month and change

13-10 in the last month, 91.5 win pace. I guess the 'and change' is doing some heavy lifting here? But either way, obviously 'limping' along as a pace better than you predicted at the beginning of the season for the last month. 

 

Any reference to Andrew Vaughn and his huge sample size of 15 games of success is laughable. Terrible defender with 1800 PAs from 2022-2024 that resulted in a .319 xwOBA. Came off that rousing success by getting cut by the 2nd worst team in baseball for his .219 OBP. 

[SB in SC]

Probably in the minority, but I do not want to see the Cubs go all in to win this year.  Some of the things happening this series we have seen coming and this series has thrown it in our face.   Hoyer went outside of his comfort zone for the Tucker trade and made some other good moves to get this team into the playoffs this year.  I do not see two moves that the Cubs could realistically make that to me would make them a favorite to get to the World Series.  The current team is good and will earn a play off spot.  They could get hot and win it all.

I do not want to see the Cubs gut the farm system, lose in the first round, not resign Tucker and be bad for the next 5 years.  

[Outshined_One]

14 minutes ago, SB in SC said:

I do not want to see the Cubs gut the farm system, lose in the first round, not resign Tucker and be bad for the next 5 years.  

This isn't 2015, though.  The current AAA grouping does not appear to have a position player on the same caliber as, say, Kris Bryant or Javier Baez, and the current mix of pitchers in the upper minors involves a promising flamethrower coming off major surgery (Wiggins) and a lot of guys with unclear ceilings.

Put another way, we're likely not looking at a wave of future All Stars coming up to kick ass and take names over the next two years.  The Cubs have a good group of guys on the farm, and it's possible one or more of them breaks out, but recent experience PCA and Shaw have taught us that we will need to exercise a ton of patience with their hitters while they figure things out.  They are also looking at a roster crunch going into next season because some of those prospects will need to be on the major league roster.

If anything, now is the time to push some of those chips to the center of the table.

[Jeff Alson]

I agree with SB that we should not decimate the farm. Whether we are competitive in the playoffs is much more dependant on whether Tucker and Suzuki break out of their deep slumps (and to a lesser degree, Happ, Swanson, and Busch as well) than on whether we trade for the types of players available over the next 30 hours.

And this is not 2016 where were clearly a playoff favorite and needed a closer to plug our one obvious hole. Even if trade a couple of out top prospects to get a #3 starter, a good reliever, and a bench bat  we will be clear underdogs to the Dodgers and Phillies, and maybe others. The marginal improvement this year is not worth the prospect capital.

I play poker, and the analogy would be calling a large bet when the odds are that you are the second or third best hand. 

[Jason Ross]

11 minutes ago, Jeff Alson said:

I agree with SB that we should not decimate the farm. Whether we are competitive in the playoffs is much more dependant on whether Tucker and Suzuki break out of their deep slumps (and to a lesser degree, Happ, Swanson, and Busch as well) than on whether we trade for the types of players available over the next 30 hours.

And this is not 2016 where were clearly a playoff favorite and needed a closer to plug our one obvious hole. Even if trade a couple of out top prospects to get a #3 starter, a good reliever, and a bench bat  we will be clear underdogs to the Dodgers and Phillies, and maybe others. The marginal improvement this year is not worth the prospect capital.

I play poker, and the analogy would be calling a large bet when the odds are that you are the second or third best hand. 

I don't like the poker analogy here, because chips in poker don't go bad. In many ways, the Cubs have a log jam in Iowa that is a misuse of assets if they hug 'em all. There is no obvious pathway to keep Alcantara and Caissie, for example or really use them by 2027. They can't really keep them all and it be a good usage of their chips. The same goes for Long and Ballesteros in many ways. Christian Franklin and a few of their lower-end arms like Assad, Wicks, Birdsel and Sanders all occupy similar positions in the organization. Players run out of options and their value in a trade depreciate over time, fairly or unfairly. Owen Caissie repeating Triple-A next year will not help anything; he either hits well and no one cares "it's his third time!" or he doesn't and everyone freaks out. The Cubs assets are depreciating values in many ways, and need to be treated as such. If you don't use them, they will lose perceived value.

I wouldn't advocate the Cubs to trade Owen Caissie, Jaxon Wiggins and Assad and Long for, say, all rentals, but I don't think that's what anyone has said here. They should be cashing in some of these assets for controllable players where they can. A SP like Edward Cabrera will be here for this year and a few more. The Cubs are a better team in 2025 for sure, and likely beyond, for doing that. 

[gflore34]

What was the score of today' game?  How GB's did the offensively superior Brewers hit?  How many X-base hits did the Cubs have today? Guess which team leads all of baseball in road wins? Hint it's not your Brewers.  Not bad for a pathetic inferior team.

Edited July 30, 2025 by gflore34

[Jeff Alson]

I agree with Jason that prospects depreciate over time. But we will need a bench OF/PH in September and hopefully October this year, in 2026 we will need a starting OF unless we sign Tucker (maybe we have a 20 or 30% of signing him?), and in 2027 we may need multiple starting OFs. I support trading either Caussie or Alcantara, but not both. And I am fine trading anyone else outside of the top 5. But I disagree with trading multiple Top 5 prospects. 

[gflore34]

6 hours ago, squally1313 said:

PCA's last 40 games date back to 6/9 (nice). Over that stretch he has a 127 wRC and the 12th most fWAR in baseball. Those warts are really coming out!

 

13-10 in the last month, 91.5 win pace. I guess the 'and change' is doing some heavy lifting here? But either way, obviously 'limping' along as a pace better than you predicted at the beginning of the season for the last month. 

 

Any reference to Andrew Vaughn and his huge sample size of 15 games of success is laughable. Terrible defender with 1800 PAs from 2022-2024 that resulted in a .319 xwOBA. Came off that rousing success by getting cut by the 2nd worst team in baseball for his .219 OBP. 

To minimize PCA's season, which is thus far, setting at an NL leading 6.3 WAR, and prop up Vaughn sporting a career WAR of 0.2 is something.

[Jason Ross]

29 minutes ago, Jeff Alson said:

I agree with Jason that prospects depreciate over time. But we will need a bench OF/PH in September and hopefully October this year, in 2026 we will need a starting OF unless we sign Tucker (maybe we have a 20 or 30% of signing him?), and in 2027 we may need multiple starting OFs. I support trading either Caussie or Alcantara, but not both. And I am fine trading anyone else outside of the top 5. But I disagree with trading multiple Top 5 prospects. 

The Cubs have Christian Franklin who is a really nice little fourth-OF prospect. He's sporting a wRC+ over 130 since June 18th in Iowa (he had a really rough run for about a month and change) and is capable at all three positions. They could trade both OF'ers and still have a ready made backup. 

Don't forget long term, the Cubs just drafted Ethan Conrad and Kane Kepley from college. The former has batted ball data at WF before injury that was pretty close to Cam Smith's last year and Kepley is a 70 grade defender and 60+ grade runner with strong contact skills. Both could conceivably be options in 2027. As well as 6th round overslot ($2m to be exact and the 2nd highest bonus in the draft) prep-OF Josiah Hartshorn. The Cubs have gone ahead and nabbed a few more interesting OF'ers. 

I think any trade in which the Cubs include Caissie to begin with will bring in a controlled player for next year, so while I don't want to trade them all away, I think the Cubs will be fine regardless of what occurs in the next 24 hours.