#2 - Sell
You'll see in a moment how the most likely scenario still includes this, but something that John Mozeliak has talked a lot about when it comes to this team is the ROI (return on investment) that the club can get from their impending free agents.
If you look around baseball, there are about 20-24 teams that I can see being "buyers" at this year's trade deadline because of the expanded playoffs and how bunched up teams are this year. Of those 24 teams, 18 of them should be fairly aggressive when it comes to adding talent.
That leaves us with 6-10 true sellers in this year's trade market. And when you compare the Cardinals assets to teams like the Nationals, Rockies, Athletics, Royals, and Tigers, you'll see why the Cardinals' front office may want to capitlize on their talent.
First, here's what they won't be selling. They will not be trading away Paul Goldschmidt, Nolan Arenado, Willson Contreras, or guys like that for a full blown rebuild. It's not happening. But they do have assets that can bring them back significant talent.
While Jack Flaherty and Jordan Montgomery have not been studs by any means this year, when you compare them to the other pitchers available on the market, they will actually be two of the strongest names available. Not only that, but almost every buyer in this year's market is going to be looking for starting pitching help. This means St. Louis will likely get more in return for those two starters than you would normally expect.
Jordan Hicks has been one of the best relievers in baseball as of late, and should fetch a really nice return as well for a contender looking to add elite stuff to their late inning group. Tyler O'Neill is a prime bounce back candidate that other teams will be interested in. Ryan Helsley, Giovanny Gallegos, and Genesis Cabrera are guys the Cardinals could captilzie on the value of as well. Even guys like Chris Stratton, Paul DeJong, and Drew VerHagen could grab value for them.
The Cardinals are going to lose Flaherty, Montgomery, and Hicks this offseason anyways. Why not just free up payroll with their depatures this offseason but also grab some valuable assets in the process?
But here is what I see, in combination with this scenario, as the Cardinals' number one strategy at this year's deadline.