2. Extend Jordan Montgomery instead of Miles Mikolas
In the spring, after the dust had settled from a boring offseason, the Cardinals made a crucial mistake.
Miles Mikolas was given a two-year contract extension that would take him through the 2025 season.
This is not a knock on Mikolas in any way, and I'm not suggesting that he's a bad pitcher. But the results from the 2023 season speak for themselves.
Mikolas went 9-13 and posted a disappointing 4.78 ERA last season. Meanwhile, Jordan Montgomery played the role of the ace for the Rangers and led them to a World Series title after the Cardinals had traded him.
Montgomery is only 31 now, and the Cardinals could have extended him at a good price last spring had they just been willing to give him what he wanted.
He's a free agent now, so there is a small chance the Cardinals could come calling if the price goes down, but they wouldn't have to worry about that right now if they had only chosen to extend him instead of Mikolas.
He proved himself as a viable postseason starter last October, and the Cardinals certainly could have benefitted from that. Even if the Cardinals had fallen out of contention, they could have instead traded Mikolas and still had Montgomery under club control for at least a few more seasons.
He alone wouldn't have saved the Cardinals however, which brings us to our next point.