#2 - Jack Flaherty
One of the most devise players amongst Cardinals fans, Jack Flaherty is entering the most important season of his career in 2023 and could reestablish himself as one of the best pitchers in all of baseball.
Extending him now would be a high-risk, high-reward move for the club. His value is not as high as it could be after the 2023 season, so the Cardinals may be able to strike a bargain similar to the Tyler Glasnow extension that the Rays handed out. It would likely be a 2-3 year deal at most but would keep him in St. Louis as a cheaper AAV than he would have on the open market as Flaherty looks to up his value once again.
Why would Flaherty do this? Well, he just recently turned 27, so he does not need to lock himself into a long-term deal yet if he thinks he can get back to his 2019 production, where he went 11-8 with a 2.75 ERA and had a historic second-half showing. Still, his injuries the last few years adds risk to a large multi-year deal, so Flaherty could ensure he gets paid in case of injury over the next few years, but the hope would be for both sides that he rebuilds his value before entering free agency for a massive deal at age 30 or 31.
I know there is going to be a group of people who balk at this idea, but if Flaherty is open to it, the Cardinals should seriously consider it. I'm not talking about some massive 6-year extension. I'm looking at a 2-3 year deal between $15-$18 million per season. The Cardinals get a $10-$15 million per year discount than what Flaherty would receive on the open market if he returns to form in 2023. If Flaherty does not return to full form but remains healthy, he'll likely pitch well enough to at least justify that number as well. The only way this deal goes wrong is if he continues to struggle with major injuries.