5. Not signing one of the big-name shortstops (kind of)
The last decision on this list is probably the one that you can argue against the most, but here's why in hindsight I think it made sense to pass on the free-agent shortstop market...for the most part.
It's hard to argue that this team shouldn't have signed Corey Seager, Marcus Semien, or Trea Turner when they had the opportunity to. All three, especially the first two, have been great gets for their clubs so far and the Cardinals would easily be a better team with them. If the Cardinals were willing to expand their budget further than they do right now, it would be even more of a no-brainer, especially compared to the Soto situation, where a deal also required a bunch of young talent.
There are a few reasons why I think it may have made sense to avoid that market though, but only if the club ends up investing in other areas in the next few seasons. Masyn Winn is not one of those players, and while he could develop into one, passing on those three guys I mentioned before because of his promise alone is a mistake. But saving that money to invest into the true weaknesses of this club does make sense, something we really haven't seen St. Louis do yet.
Let's take a brief look at each of the major free agent shortstop contracts signed from the previous two offseasons.
Corey Seager - ten years, $305 million
Marcus Semien - six years, $110 million
Trevor Story - six years, $140 million
Javier Baez - six years, $140 million
Carlos Correa (twice) - three years, $1053 million with opt-outs, and then six years, $200 million
Trea Turner - eleven years, $300 million
Xander Bogaerts - eleven years, $280 million
Dansby Swanson - seven years, $177 million
Out of all of those contracts, I really only think you'd want to have Seager, Semien, or Turner. Story and Baez have already been major busts, while Swanson and Bogaerts will not age well at all. Correa may end up being a good deal, but I'm not too upset about that one.
Part of this argument again hinges on the fact that the Cardinals just are not going to spend like the biggest markets in baseball. Yes, they do need to spend more, I 100% agree, but they just are not going to compete in spending with Los Angeles and New York. So at some point, they need to be aware of how they are spending and make sure they have financial flexibility to upgrade other parts of their roster.
I really wish one of Seager, Semien, or Turner was in the Cardinals lineup. They would probably have the best unit in all of baseball. But If they end up deciding to upgrade their pitching next offseason with the freed-up money they have organizationally, then I see the reasoning. But if they had signed any of the other shortstops, it would have been a massive mistake in my opinion.