Cardinals: Ranking the rumored extension candidates for St. Louis

The St. Louis Cardinals appear to be done with most of their major business this off-season, signing Willson Contreras to succeed Yadier Molina behind the plate in 2023. While they may not make any other significant moves between now and Opening Day, they are reportedly looking to extend some of their arbitration-eligible players.

According to John Denton of MLB.com, the Cardinals had hopes of agreeing to long-term extensions with Jordan Montgomery, Jack Flaherty, Tommy Edman, and Ryan Helsley before the arbitration deadline on Friday. They were unable to do so, instead settling with Montgomery, Flaherty, and Edman while heading to arbitration with Helsley. This raises an interesting question, which of the four should the Cardinals prioritize in extension talks?

An argument can be made for all four of these players that it would be in the Cardinals' best interest to retain them for their long-term plans. Both Flaherty and Montgomery would add another arm to their 2024 rotation and beyond, that currently only has one returning member beyond this season in the form of Steven Matz. Ryan Helsley just had an incredible season as the club's closer, and will likely become expensive in arbitration if he repeats that again in 2023. Edman has become one of the most valuable position players for St. Louis, playing elite defense and being a consistent contributor for the lineup.

It's highly unlikely they'll be able to extend all four of them, but it is realistic to think that one or two of these players could receive a long-term extension before the regular season begins. Here is how I would rank the four players in terms of who the Cardinals should prioritize extending.

#4 - Ryan Helsley

The tough part about this list is that all four guys would be great extension candidates. But if I had to put them in order, Ryan Helsley would be the least pressing of the candidates.

For starters, Helsley has multiple years of club control remaining, so there is no rush to get an extension done with the flamethrower. Yes, his extension number will rise significantly if he repeats his 2022 performance or even comes close to it, but that is a risk that is probably worth taking for the Cardinals. Unless Helsley is looking for a very team-friendly deal this off-season, it could be risky extending him.

Helsley had a career year in his age-27 season, posting a 1.25 ERA with a 13.08 K/9 in 64.2 innings of work. He was dazzling fans and experts alike with his fastball velocity and ability to throw hitters off with great off-speed options. While his stuff should continue to play, relievers are notorious for falling off at any moment. Without much of a track record outside of last season,

That is taking nothing away from the player Helsley has become. This has more to do with risk versus reward. St. Louis appeared to be open to dealing Helsley this off-season for a new catcher, and that likely had more to do with how the game values relievers rather than his ability. If the Cardinals do extend him, I don't think any of us would mind that at all.

#3 - Jordan Montgomery

Since being acquired from the New York Yankees in the Harrison Bader trade, Jordan Montgomery has been one of the most reliable pitchers on the Cardinals' staff.

In his 11 starts after the trade deadline, Montgomery went 6-3 with a 3.11 ERA over 63.2 innings while helping lock down the rotation as the Cardinals ran away with the NL Central title. Standing at 6-6, the big lefty is looking to build upon his success in St. Louis as he finds himself a year away from free agency.

Since debuting in 2017 for the Yankees, he has a career 3.85 ERA but really appeared to find a new level to his game after coming over to the Cardinals after the trade deadline. Montgomery has been a popular name this off-season to get an extension to provide more clarity for their rotation beyond 2023, but I am a bit more cautious than most are.

First, although Montgomery stepped it up a notch for the Cardinals, he doesn't have the ceiling of a front-line starter that the Cardinals currently lack most. Sure, he'd be a great member of the five-man group for years to come, but when it comes to prioritizing who to retain, the Cardinals need to keep guys with ace-like stuff.

The second reason I'd rank him three on this list is that there's a non-arbitration pitcher in a contract year who is also in a contract year in Miles Mikolas who may be better as the club's number two or number three starter in 2024 and beyond. Mikolas was an All-Star in 2022 and a Cy Young candidate back in 2018, and although he's four years older than Montgomery, he's been the better of the two during their careers.

Again, if the Cardinals extend Montgomery, it would be a good move for the club. I just think there's a gap between the top two guys and Montgomery.

#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.