Disclaimer: Just my personal opinions, others will disagree, this is all subjective, etc etc.
S Tier trades
Esteury Ruiz for William Contreras and Joel Payamps
This one doesn't warrant much debate about where it should fall. It was an absolute homerun.
Adam Lind for Freddy Peralta, Carlos Herrera, and Daniel Missaki
I'm not sure exactly where the careers of Herrera and Daniel Missaki went, and it makes no difference for the purposes of grading this trade. Getting a career of a starting pitcher the caliber of a Freddy Peralta for 1 year of a so-so first baseman is as good as it gets.
Lewis Brinson, Monte Harrison, Isan Diaz, and Jordan Yamamoto for Christian Yelich
This one is a bit more complex, taking into account that Yelich had a few down years after a couple years of MVP level play. However, this still falls into the S tier when you get two MVP level years of a prime player, and nothing that the Brewers gave up ended up being something sorely missed.
Justin Chambers for Bryan Hudson
Hudson is crushing it for the Brewers pen and they have numerous years of bullpen control here. How can it not be S tier?
A Tier -
Josh Hader for Robert Gasser, Dinelson Lamet, Taylor Rogers, Esteury Ruiz
The only reason that I'm excluding this trade from the S tier is 1) because I'm grading the Ruiz trade on a standalone basis, and 2) The argument could be made that this trade hurt the Brewers in the pennant race that season. Still, on paper, getting years of Robert Gasser, along with a prospect on the tier of Ruiz for what was only going to be a 1.5 year rental of an expensive Hader, puts this at least on the A tier.
Hunter Renfroe for Janson Junk, Elvis Peguero, and Adam Seminaris
Renfroe is doing nothing for the Angels – without even knowing what we will get out of Junk, the value of Peguero alone in the bullpen has made this one worthwhile. This falls into the A tier only for having less value than some of the S tier trades above.
Corbin Burnes for DL Hall, Joey Ortiz, and 34th overall pick in 2024
Again, Ortiz, who looks like a budding star, makes this look like a potential great deal, without yet knowing what we'll get out of Hall and the 34th pick. I can't put it on the S tier, because Burnes is still a fantastic asset who would arguably have made us better this year. However, Ortiz has been too good to put it lower than A.
Taylor Floyd for Trevor Megill
The Twins got a minor league body, and the Brewers got a great arm for their pen and an interim closer. That'll do.
Cash for Bryse Wilson
Bryse has been a pretty key swingman in the pen. Given what they gave up to acquire him, another great deal.
B Tier
Drew Rasmussen and JP Feyereisen for Willy Adames
This is probably one of the few trades that it is reasonable to argue that the Brewers took the loss on, although it would also be reasonable to argue that they didn't. Rasmussen was converted to a started by the Rays and flourished as one when healthy, but has still struggled with injuries. Feyereisen provided some good value before also succumbing to injuries. Adames has been up and down for the Brewers, but the highs have exceeded the lows.
C Tier
Hendry Mendez and Robert Moore for Oliver Dunn
Mendez and Moore are somewhat intriguing but nothing to panic about losing at this point. Dunn has been a meh role player for the Brewers, but not useless.
D Tier
Brian Sanchez and Jace Avina for Jake Bauers
Sanchez and Avina both are having really fantastic minor league seasons. Though they're young lottery tickets and a long ways away from knowing if it'll ever translate to big league success, trading either for a journeyman like Bauers would be a large loss if either pans out.
A few observations
This is not a very homegrown roster, it was mostly assembled by trade. That is not a criticism, just an observation.
Say what you want about the draft misses by this organization, but the trade results have been nothing short of fantastic. This is a very underrated front office. The homeruns are plentiful. The misses are few and at this point, minor.
The Brewers pitching lab might be one of their most valuable assets. Not a coincidence that most of the hits involve pitching, and the success of this lab extends beyond just trade acquisitions, as we see with guys like Colin Rea.