It has to make sense for the player too, so the player you’re thinking of is probably not what this is about
There was a long-standing assumption, pretty much since Paul Goldschmidt won his MVP, that he would receive an extension during the current spring training. That appears to not be happening. It certainly makes sense. The Cardinals have a few internal candidates who could look like equal or better options to Goldy by the end of 2024, and certainly cheaper options. There is not a lot of upside to an extension and a whole lot of downside.
Maybe it makes sense to extend somebody else? Well, let’s find out. I don’t think it’s as simple as some people make it out to be. It has to make sense for both the team and the player and unless the player is really committed to getting his guaranteed money on the books now, those interests rarely align.
The player has to have some reason to reduce risk and get the guaranteed money. This usually means the player is a pitcher, an unheralded position player prospect, or a player whose skillset doesn’t demand large free agent prices in the first place. This describes Carlos Martinez, Matt Carpenter, Kolten Wong, Stephen Piscotty, Allen Craig, and Paul DeJong.
Carpenter and Craig were never really prospects because they were always old for their level, and Wong and Piscotty were back half top 100 prospects but ones who lacked upside. DeJong was barely a top 10 team prospect, and obviously Martinez was a pitcher. And frankly, with the exception of Carpenter, these were all great extensions for the player. (I’m referring to Carpenter’s first team-friendly extension).
You can see where I’m going with this right? Nolan Gorman is a popular extension candidate from fans, but Nolan Gorman has no reason to sign an extension. Especially right now. If you’re a player and you think you haven’t reached your full potential and that you will reach it, you shouldn’t sign an extension. Same applies to Jordan Walker. There’s no reason for you give a bargain to the team. Both also have skillsets that will get paid in free agency. Gorman will hit free agency at 29, Walker at 28.
I know people want the Cardinals to sign these guys to a team-friendly extension, but if I’m their agent, I’m advising them not to, unless the Cardinals blow me away. The Cardinals have no reason to agree to that though. They already have Walker for six years, and Gorman for five years.
So in searching for potential extension candidates where I think the other side might be amenable for one reason or another, there are surprisingly few candidates. All the pitchers are old, and I would never sign a reliever to an extension (if one must, Gallegos’s contract is a very good one). The starting pitching prospects probably should at least debut in the majors before you consider a long-term deal.
So if I’m eliminating Walker and Gorman, that really only leaves two candidates: Masyn Winn and Brendan Donovan. In theory, there’s a narrow window where Winn makes sense for both sides. Capitalize on Winn being unproven and sign him to an extension from the Cardinals’ perspective and for Winn, get that guaranteed money now while he’s unproven. Of course, this requires some cooperation from Winn and it may make the most sense to him to prove himself first and raise any potential extension price. Or just reach free agency at 28 like Walker.
In Donovan’s case, he is a direct comp to Matt Carpenter. Carpenter signed his first extension in spring training 2014, when he had 2 years and change of service time. Brendan Donovan is currently in spring training when he has exactly 2 years of service time. They aren’t the same type of hitter, but both had the same amount of acclaim as prospects (none), play multiple positions, and four years left until they hit free agency. Donovan is a year younger, and will be a free agent a year earlier. But waiting to get a big payday at 31 (when he’s first eligible) is a bit of a risk. So I could see it. Let’s formulate what extensions might look like.
Masyn Winn
We have Winn’s ZiPS projection through age 24, which is helpful, though I’d still like to know his projection through age 26, because his projection rises each year, and I’m not entirely sure at what point it would start declining. I say age 26, because I would personally guess that’s the age where it starts being more static. But hell, I can guess. His three-year projections are
2024: 2.4
2025: 2.6
2026: 2.9
The 2024 number is very optimistic and not something I would base a contract on – it’s far too reliant on elite defensive numbers and I trust ZiPS defensive metrics a little bit more than George Santos. But just a bit. However, it’s kind of irrelevant for the purposes of an extension weirdly enough. His projection for 2024 and 2025 don’t really matter. Those are league minimum years. His 2026 number matters very much because that year defines what his arbitration salaries will be, and thus the framework behind the deal.
One assumption I have to make is what Winn’s age 25 season will look like, and because I assume ZiPS thinks a player will, on average, improve from age 24 to age 25, I have his 2027 at 3.2 WAR. I am also going to assume that his age 26 WAR will stay at 3.2 WAR. Thus, his entire extension will be defined by two things: his arbitration salaries based upon being a 2.9 WAR player and his free agent salary based upon being a 3.2 WAR player. That’s where we go from there.
Point of Pittbsurgh, which might be a bit outdated, but it doesn’t necessarily matter for the sake of an extension, says that players will typically get 25% of their free agent value in year 1, 40% in year 2, and 62% in year 3. At $10 million per win (and thus being valued at $29 million), that means Winn is currently projected to earn $7.3 million, $11.6 million, and $18 million.
Picking how many years to make the deal is tricky, because hypothetically Winn might still want to be set to reach free agency at a reasonable age. Unless we’re going to make this contract really crazy, I think one free agent year and one team option year is going to have to do. Winn will still be set to be a free agent at age 30. Cards get prime years, Winn still gets a shot at a bigger payday.
Cards get a bit of a discount for the security, let’s say 80% of the overall value. That’s $57 million. We can reduce a little bit of the free agent year by giving him a pay bump for the next three years. So instead of $2.5 million for the next three years combined, he gets $2 million each year. He’ll get his normal arb prices at $7.5 million and $12 million, but we’ll have to re-arrange the next two years since he’d get less than his 3rd arbitration under this structure. So instead the next two years are at $16 million each. To increase the overall value of the deal, the team option will come with a $5 million buyout. So by signing the deal, Masyn Winn guarantees himself $62 million with a career 29 wRC+ and -0.8 fWAR. That team option year should probably reflect a free agent price, so I’ll say $25 million for that year. That means the structure of the deal is:
2024: $2 million
2025: $2 million
2026: $2 million
2027: $7.5 million
2028: $12 million
2029: $16 million
2030: $16 million
2031 $25 million ($5 million buyout)
The Cardinals don’t get very creative with their contracts, but to entice Winn further, I would maybe say if he either is top 10 in MVP voting or makes an All-Star game in 2029, $5 million is added to both his 2030 salary and his buyout. But we’ll keep it simple. His final guaranteed money would be $62 million with a $25 million option.
Yesterday in fact, Ezequiel Tovar just signed an extension somewhat similar to this (7 years, $63 million with a club option.) Difference being that he is one year closer to free agency than Winn is. So Winn technically gets less than Tovar, but he has an extra league minimum year and Tovar has an extra free agent year in his deal. So Winn’s deal, despite being less than Tovar, is actually better than Tovar’s deal. (Tovar’s team option is most likely less than $25 million as well)
I myself would sign Winn to this, I’m not sure Winn would sign it. I’m not sure the Cardinals would either quite frankly. It does not come without risk, since projections are just projections. But Winn seems like a good player to bet on.
7 years, $57 million with $25 million club option ($5 million buyout)
Brendan Donovan
Donovan doesn’t actually make sense to extend if you use projections. They are not great. Unlike Winn, they get worse every year. Carpenter was coming off his top 10 MVP finish season back in 2013, so the circumstances are a bit different when it comes to extending Brendan Donovan. His next three years are 1.8, 1.6 and 1.4 WAR. Some of that is simply plate appearances. Due to missing two months last year, he projects for about 475 PAs every year.
So we’re going to go on faith in Brendan Donovan with this extension. We’re not going to go too crazy, but we’re going to assume that 3-year projection is wrong. We will value Brendan Donovan as a 2 WAR player, that’s it. This does not seem crazy to me. Because we are mimicking the Matt Carpenter extension, some of his decline years will be featured in the deal so the WAR will decline.
Even with the underwhelming 2024 projection, he would still be valued as a 2 WAR player by arbitration I imagine, so that doesn’t change. Even though it wouldn’t be reflected in the projections, I’m also going to say his projected WAR for this contract won’t decline until he turns 31. Which just so happens to be his free agent years. This far in the future, I’m just going to make this easy and say he’s 1.5 WAR player in value both free agent years. Okay what does this contract look like?
2024: $2 million
2025: $5 million (Arb 1)
2026: $9 million (Arb 2)
2027: $11 million (Arb 3)
2028: $13 million (FA)
2029: $13 million (FA)
2030: $15 million club option ($1 million buyout)
I already explained the process for Winn, so I didn’t feel like I needed to go over that again. But here’s the logic. If he’s valued as a 2 WAR player through his arbitration years, and a 1.5 WAR player through his free agent years, for the next 6 years, he’d be worth $55 million. 90% of that value is $50 million (Donovan is more of a sure thing than Winn, hence less of a discount.) If you add up the numbers, it’s $49 million and the $1 million buyout makes it $50 million.
If you think this deal is crazy, coming off a 7.2 WAR season, Matt Carpenter signed for 6 years, $52 million. Inflation and all, but still: Donovan is coming off a much worse season than that with even more uncertainty than that. If you believe the projections, Donovan should leap at this offer.
6 years, $49 million with $15 million club option ($1 million buyout)
If you would jump at these offers, just remember how quickly people complained about the Paul DeJong deal. How the Martinez deal suddenly was a problem. How the Piscotty deal aged. The Allen Craig deal. They all looked like incredible deals at the time. I’m not saying we shouldn’t sign my proposed deals, I’m just saying there’s more risk involved than what people probably think.
And from the players’ side, they are removing of lot of upside from their earnings potential. I, a mere mortal who stopped playing baseball freshman year of high school, would jump at guaranteed money like this. But they, who have the utmost confidence in their ability and that confidence has been rewarded enormously, probably believe in themselves and their ability to reach their upside. So that’s why the team friendly extensions can be hard to do.