3. Aggressively upgrade your weaknesses
You don't even really have to follow the Cardinals to understand that they have a huge weakness when it comes to pitching. Both their rotation and their bullpen need significant rehauls between now and Spring Training, and this deadline can be the first attempt at that.
I talked about this recently, but the Cardinals need to look to sell on their impending free agents at the deadline, and then look to aggressively "buy" on controllable starting pitchers using some of their young bats at this deadline. If the opportunity presents itself where a team like the Mariners, Guardians, Marlins, or someone else with controllable starting pitching really wants one of the Cardinals' young bats not named Jordan Walker, the club has to listen to that.
I have my own opinions about who should be "shopped" vs. who should be held onto if at all possible, but realistically speaking, one of Nolan Gorman, Lars Nootbaar, Brendan Donovan, Masyn Winn, or Tommy Edman will have to be made available in order to acquire an arm with real upside and team control. Dylan Carlson is a name that could bring back a nice arm in return, but the upside and/or control will be very limited.
Packaging the likes of Luken Baker, Juan Yepez, Alec Burleson, Moises Gomez, and others with one of those names listed above could really get other clubs talking about their young arms. If a deal does not present itself at the deadline, the Cardinals can hold onto these chips until the winter, but if the deal is available now, it helps them get ahead on their offseason plans.
Next year, Miles Mikolas is the only starter I would say is "guaranteed" a rotation spot. Acquiring a controllable big league arm helps fill another one of those voids at a lower cost, and then allows the club to spend in free agency to fill 2-3 more of those gaps. Maybe Matthew Liberatore proves he is worthy of a spot over the rest of 2023? Maybe one of Michael McGreevy or Gorodan Graceffo can overtake him? Could Tink Hence possibly be ready as he has now risen to Double-A and looks spectacular this year? Any of these scenarios would help the Cardinals fill out their rotation next year.
Let's say the Cardinals pull off a deal for one of the Mariners pitchers like Logan Gilbert. Gilbert will likely make just over $1 million next season. Mikolas makes $16 million in 2024 and 2025 (which is a $4 million decrease from this cap hit this year). The Cardinals have publically stated they have more money to spend right now and also have an additional $37.5 million coming off the books with Montgomery, Flaherty, Stratton, Hicks, and Wainwright. Not to mention another $9 million or so in Paul DeJong and likely another $5 million in the form of Tyler O'Neill.
That leaves the Cardinals with, at least, close to $50 million in payroll to address one, two, or three of those other rotation spots. I could easily see St. Louis having the flexibility, if they have already acquired a young starter via trade, to fill two of those spots with free agent dollars and then allow one of Matz, Liberatore, Graceffo, or Hence to claim that final rotation spot.
A lot of that flexibility hinges on the Cardinals acquiring controllable starters though. If they cannot find a young, MLB-ready arm that they can rely on to fill one of those spots, they likely have to split that salary flexibility up even more, which won't allow them to go after some of the higher-end arms in free agency.