The last two weeks I have gone position by position comparing the Cardinals roster and prospect pipeline to the Brewers for both hittersand pitchers. My assessment was that the current and future position-player talent on both teams is relatively close and that the gap on the pitching side is quite substantial. As I looked at both teams, I considered the talent at both the major and minor league levels. Even accounting for the Cardinals’ exceptionally deep farm system, I still think the Brewers have more
talent in their organization. Point being, there is still a lot of ground for the Cardinals to make up. They aren’t going to make up this ground without taking risks, so today I am going to outline the approach I would like to see this offseason and heading into 2027.
Side note: As a fan, I would certainly be in favor of adding $80+ million to the payroll and wiping out much of the talent gap, but alas, that does not seem to be in the cards. Since the future payroll level seems to be quite ambiguous, I am going to focus on trades and extensions.
Starting Rotation
Current state: The Brewers hold a huge current advantage with Misiorowski and Henderson at the top of their rotation. The Cardinals have a clearly superior pitching pipeline.
Offseason action: Trade the depth and aggressively promote prospects
To match the Brewers’ rotation, the Cardinals need to find two top-of-the-rotation arms. Quinn Mathews is the only starting pitcher prospect likely to start the year in St. Louis, but there is a bevy of pitchers knocking on the door. Players who will need 40-man roster spots by the end of the year included Jurrangelo Cijntje, Brandon Clarke, Daniel Eagen, Mason Molina, and Braden Davis. Cooper Hjerpe and Tekoah Roby are already on the 40-man and could both start games, albeit with inning restrictions. Liam Doyle and Tanner Franklin do not have 40-man roster pressure, but both could be ready at some point during the season. If none of these nine prospects are ready next season, you might as well start the rebuild over anyway, so get them up as soon as they are ready.
Pallante and McGreevy are the perfect trade candidates. They have solid value with two and five years of team control, respectively, but neither is terribly likely to turn into a No. 2 starter. They give the team a higher floor, but they do not do much for the ceiling. Is turning over the rotation to the prospects a guaranteed path to catching the Brewers? Of course not. But hoarding fourth and fifth starters is not either.
Bullpen
Current state: Big advantage Brewers with their three-headed bullpen monster.
Offseason action: Take fliers on high-upside guys
If the Cardinals aren’t putting chips on the table for 2027, bullpen improvements will need to come internally or through under-the-radar acquisitions. The Cardinals already started this by claiming Chase Hampton off waivers from the Nationals. This is the exact type of move you like to see. Hampton has battled injuries the last three seasons, but he has flashed a plus fastball and multiple plus breaking balls at various times. There might be a 40-man roster crunch a year from now, but the Cardinals have a ton of roster flexibility to bring in lottery-ticket arms now.
If you can find a couple of interesting pieces outside the organization and get a few mini breakouts internally (looking at you, Gastelum and Santana), the Cardinals could make up a ton of ground as early as next season.
Catcher
Current state: The Brewers have William Contreras for another year, if they don’t trade him, but cannot match the Cardinals’ depth.
Offseason action: Clear the logjam
I haven’t had a problem with how the Cardinals have managed the catcher situation to date, but it is time to clear the decks. You have to bet on players at some point, and Leo Bernal looks like a good bet. Jimmy Crooks hit for a 160 wRC+ as a 24-year-old in Triple-A. Unless another team values him in a trade as an impact prospect, he needs an extended run as well.
Ivan Herrera is awesome and I will miss him, but he is expendable for the right return. The Cardinals have huge holes in center field and at third base. Herrera would be one of the best bats on the market, if made available, and should fetch a huge return.
Even with Herrera out of the picture, the Cardinals are in a much stronger position than the Brewers at catcher looking ahead.
First Base
Current state: Alec Burleson gives the Cardinals the upper hand against a (potentially) Jake Bauers-less Brewers.
Offseason action: Extend Burleson
Let’s lock in Burleson to a long-term extension. This will solidify first base as a positional advantage for the Cardinals for the foreseeable future. Burleson is growing into a leadership role and seems to be loved by the front office and coaching staff. Even if he never learns how to hit lefties, he should be a middle-of-the-order bat against righties for years to come.
Second Base
Current state: Both teams have studs in place, but Wetherholt is locked in for five years more than Turang.
Offseason action: Do nothing
This is self-explanatory. With JJ extended for eight seasons, the Brewers will have a tough time matching the Cardinals’ second-base production long-term.
Third Base
Current state: The Brewers have solid major league options in place and prospects on the way while the Cardinals are still searching.
Offseason action: Acquire a major-league-ready prospect
I am quite bullish on Blaze Jordan and wouldn’t mind giving him an extended run at third base. But if he ends up hitting, he could also help out at DH and first base. I would like to see the Cardinals add some upside from outside the organization by building a trade package around Michael McGreevy and/or Andre Pallante. The top of this market would be someone like Jefferson Rojas, the top-100 infield prospect the Mets acquired from the Cubs at the trade deadline. Sure, Jesus Baez might be the answer, but having multiple starting-caliber players would be a great problem to have.
Shortstop
Current state: Cardinals slight edge now, but the Brewers have a superprospect coming.
Offseason action: Extend Winn
Let’s not overthink this. If Winn is open to it, lock in a five- or six-year contract. More control would only make Winn more valuable as a potential trade chip if a player from the system emerges as a better option. The most exciting shortstop prospects are in the low minors (Sebastian Dos Santos, Miguel Hernandez, Yairo Padilla, and Rocco Maniscalco), so getting Winn locked in long-term gives the Cardinals some certainty.
The Brewers have the game’s top prospect in Jesus Made on the way, but it is not a foregone conclusion he will be able to match Winn’s overall production.
Left Field
Current state: Brewers have a star in Chourio and the Cardinals hope to have one in Joshua Baez.
Offseason action: Do nothing
If the Cardinals were in a win-now mode, you would want more depth behind Joshua Baez. But for where they are at, he is the perfect player to pencil into the lineup every day and see what you have.
Center Field
Current state: The Brewers got a great season from Mitchell, but may be vulnerable going forward. The Cardinals should still be searching.
Offseason action: Acquire the center fielder of the future
Apparently the Cardinals are fine starting the season with Nathan Church in center field. This is where I would like to see the Cardinals get aggressive about prioritizing finding an impact talent. Would a package built around Ivan Herrera be enough to bring back one of the blocked Dodgers outfield prospects, Mike Sirota or Eduardo Quintero? The Dodgers have a pretty good DH already, so that scenario would likely require a three-team trade. The Braves look like a more logical fit for Herrera and have one of this year’s breakout prospects in Eric Hartman. Cleveland has a top-100 center fielder in Aaron Walton, who climbed to Double-A in his first professional season.
There really aren’t many upper-minors center field prospects to pick from across baseball, so this route could take some creativity, but if Bloom can turn the catcher surplus into a chance at an impact outfielder, that would be a huge win for the organization.
Right Field
Current state: Jordan Walker outperformed the only black hole in Milwaukee’s lineup.
Offseason action: Do nothing
I do not think this one needs much explanation either. The 2026 Cardinals’ arc mirrored Walker’s last season, and that could very well be the case in 2027. Walker has obviously earned plenty of runway. The general consensus seems to be that a long-term extension does not make sense for either side at this point in time. I tend to agree with that, but if the numbers work out, I would love to see the Cardinals explore this.
Designated Hitter
Current state: Cardinals with the advantage based on Yelich’s contract situation.
Offseason action: Do nothing
In the scenario I have outlined, DH is the one area that potentially becomes problematic with Ivan Herrera traded away. Still, I think you have to roll the dice and try to mix and match. Bernal might be a good enough hitter to warrant DHing on some of his off days from catching. Blaze Jordan could be a good option, especially against lefties. This could also be an excellent way to ease in Rainiel Rodriguez when he makes his debut. I also think Deniel Ortiz is the most underrated prospect in the system. His defense is a question mark, but I think he is going to hit at the major league level and could be in play as early as midseason.
Conclusion
There you have it. Extend Burleson and Winn. Trade McGreevy, Pallante, and Herrera to shore up the remaining holes on the position-player side. Take a few fliers on high-upside relief arms, and buckle up for wave two of the youth movement. Best-case scenario: the young pitchers outperform expectations and push the team to contention ahead of schedule. Worst-case scenario: you get some of the learning curve out of the way and get even more answers on what the future core looks like. Catching the Brewers will require patience and a bit of luck, but some aggression and risk-taking will be required as well.
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