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Is there an extension candidate on Cards?

Is there a potential deal for both sides anywhere on the roster?

MLB: St. Louis Cardinals at Cincinnati Reds Katie Stratman-USA TODAY Sports

Before the pandemic, the Cardinals were an extension happy team. Just look at the 2019 team. Paul Goldschmidt signed an extension in spring training a year before needed. Matt Carpenter signed an extension in April, over a year before needed. They signed Carlos Martinez to a five-year extension before he reached arbitration, locking up two free agent years. Yadier Molina was in the middle of a three-year contract extension he signed in April a year before free agency. Kolten Wong was in the middle of a five-year contract extension he signed during his pre-arbitration seasons. And Paul DeJong was in the beginning stages of his extension as well, shortly after debuting.

Maybe they’ve changed their mind due to the results. Carpenter, DeJong, and Martinez did not turn out well. Molina was a special case. Goldschmidt has worked out as well as possible and Wong’s extension turned out pretty well too. Even in the case of the ones that didn’t work out, the damage was minimal. It’s possible they’ve turned away from these. Or maybe the pandemic is why they didn’t, and now that the money is flowing, we can expect extensions again.

The Cardinals did not discriminate on who to hand out extensions too. In the examples above, we have an extension to a player with very little track record and less than a year of service time (DeJong), a pre-arbitration player a year away from arbitration, a player entering his first year of arbitration (Martinez), multiple players who signed an extensions before their contract year (Mikolas, Molina, Goldschmidt), and then an extension almost two full years before needed (Carpenter). This is just about every possible extension that could exist, with the exception of signing a player who never played in the majors.

There are a lot of candidates for their most popular extension, the year away from free agency. Couple that with needing to replace four members of the 2022 rotation and you have a recipe where a starting pitching extension seems like it will be announced sometime in spring training. Goldschmidt signed his extension on March 23rd, Mikolas on February 26th, and Molina on April 2nd. Carpenter signed his a week into the season, on April 10th. Let’s look at the candidates.

A Year Early

Mikolas has already signed an extension like this, and will be entering free agency at 35-years-old, so he probably has a strong incentive to sign an extension if possible. Where things may hit a snag is in the years. A two-year extension for Mikolas seems fine, three years does not. It’s a different story when he would reach free agency, because then at least we’d have a good idea of what he did in 2022.

Steamer seems low on Mikolas. They have him for 2.1 WAR in 191 innings. The innings are too high, but to give you an example of why I think that is low, I looked at ZiPS 2022 projection for Mikolas and he was projected for 1.4 WAR in 111.1 IP. In 191 innings, that’d be 2.4 WAR. On a rate basis, I guarantee ZiPS is going to have a better projection, it’s just a matter of how many innings they think. I do think it’ll be more than 2.1 WAR ultimately though.

This is where extension talk gets tricky. I’ve seen talk that you just give him his current $17 million salary and you can do that, but really only if he’s willing to go 2 years. Let’s say he’s a 2.4 WAR pitcher, which is optimistic from a projection standpoint anyway. That means his 2024 is 1.9 and 2025 is 1.4. That comes out to 2 years, $34.7 million. (at $10.5 million per win) Perfect. But for three years? Not so much. His 2026 is now 0.9 WAR. A 3 year deal comes out to 3 years, $44.1 million. I don’t think there’s much incentive to jump at a 3 year, $51 million deal. I don’t think he’s going to do better than Chris Bassitt, who signed a 3 year, $63 million. The potential outcomes that lead him to be worth less than $51 million are a lot more than the potential outcomes that lead to him being valued at 3 years, $63 million, which feels like his absolute ceiling.

How about Jordan Montgomery? In his case, Montgomery will be less inclined to sign a deal, so I can’t exactly map out his future contract using projections. He’s valued as a 2.5 WAR pitcher by Steamer and that feels like a fine place to start for his 2024 valuation. Instead of 0.5, I decline by 0.3 before the age of 32. Since he’ll be 31 at the start of this extension, that’s 2.5, 2.2, 1.7, 1.2, 0.7 for the future years. I think you’d probably need five years to get it done. 5 years, $87.2 million. Unlike Mikolas, I can easily see him making over $100 million, so there is more incentive to avoid going to free agency. But obviously, we have no idea what’s on the table for Montgomery to sign.

I couldn’t even posit a guess as to what Flaherty would get, but an extension couldn’t make less sense for either side. Flaherty is far too high risk to sign to an extension before we see some evidence he’s returned and in the case of Flaherty, any potential extension will probably pale in comparison to his earning potential if he at all returns to his previous self. So I’m not even going to speculate.


The only player who fits the Paul DeJong model is Brendan Donovan, and if the Cardinals had a hole aside from him at 2B like they did at shortstop, he might make sense. But with Tommy Edman, Masyn Winn, and Nolan Gorman currently employed, there’s just no reason to lock him up.

An interesting player to sign to an extension who makes a lot of sense if the Cardinals had reason to believe in him would be Dylan Carlson. Short of that, he doesn’t, especially with his hard hit issues. There was a recent Fangraphs article that concluded we can predict future hard hit with a shocking degree of accuracy after a rookie puts 300 balls in play. In other words, just going by the stats, he’s not very likely to suddenly hit the ball hard if he hasn’t already.

And then we have Lars Nootbaar. Hypothetically, we have merging interests in an extension. Nootbaar has sort of proven himself, but not completely so Nootbaar might want to jump on the guaranteed money. On the other hand, Nootbaar has sort of proved himself, but not completely so the Cards may want to jump before he does it completely and becomes more expensive. But Nootbaar is, well, how do I put this? Let’s just say his grandfather was a major donor to the USC Hall of Fame building, to the point where it is named after him. He can afford to bet on himself.

First Year of Arb

In this category we have Tommy Edman and only Tommy Edman. Technically we also have Ryan Helsley, but in none of the examples is there a long-term reliever contract, so I don’t think he’s a serious candidate. Edman is kind of in a similar position to Martinez when he signed the deal. He was proven and had logged back-to-back 3 fWAR seasons. If Edman didn’t just have a 5.6 fWAR season, it’d in fact be a near perfect comparison, despite the position difference.

But that 5.6 fWAR season complicates things. He’s not going to have a better season than that, so you are essentially paying him based on his best season, which is never a good idea. Especially if you don’t actually have to do that, like in free agency. But hypothetically, let’s give him a comparable deal to Martinez, who I must point out was three years younger than Edman when he signed his deal. So Martinez’s deal took him to, best case, his age 31 season. A similar structure for Edman would take him to age 34.

He “should” make $21.5 million in his arbitration years if his arbitration years are accurate. By the time he would hit free agency, I have him as a 2.5 WAR player, making the two free agent years in his deal 2.5 WAR and 2.2 WAR. That’s $49 million in value, but since we’re signing an extension, we’ll slap on a 75% discount. That’s still $18.5 million per year. But part of the incentive for an extension from the player’s point of view is more money now. So we’ll knock $9 million off the later years, and apply it to the arb years. Now in free agency he’s making $14 million in the two years.

But there’s some more accounting trickery I can do. Because this deal would include two buyout years. If we make the buyout $4 million, now his two free agent years are $12 million, but he still is guaranteed the same amount of money. His buyout years would be $15 million and likely to be bought out but who knows? So let’s say $5 million bonus, $1 million each year of his guaranteed years, then $6 million, $8 million, $11 million, $12 million, $12 million with two $15 million options.

It comes out to 5 years, $46 million guaranteed with two club options. Sounds great, but Edman is a fairly similar player to Kolten Wong - definitely better, but similar shape of value - and Wong is in the third year of a 3 year, $26 million he signed a year younger than Edman would be when he enters free agency and in fact Wong just got traded and the Brewers threw in a little bit of money. And we don’t know that Edman will look like a better free agent in three years.

Plus, you know, Masyn Winn. Might want to figure out if he’s the future before committing to Edman for that long.

In my post on the 2024 rotation, I made the argument that the Cardinals should resist the temptation to sign an extension. I still stand by that, even though I kind of expect it to happen. Despite being so extension heavy in the past, I’m not sure there’s an extension with the current players that necessarily makes sense for both parties involved. And that’s okay.