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What would a Jack Flaherty extension look like?

I try to come up with a couple of different extensions that won’t happen

Wild Card Round - St Louis Cardinals v San Diego Padres - Game Three Photo by Sean M. Haffey/Getty Images

There’s a recent rumor out there that Fernando Tatis is about to sign a 10 or 11 year extension for about $320 million. Since this is a Cardinals blog, I’m not going to write a post about that. Although my two cents are that... this seems pretty stupid from the Padres perspective. He’d get about $40-50 million in arbitration if he’s as good as expected. I expect the 11 year is the more accurate rumor because with an extension, his free agent years would then be $38.5 million a year for 7 years. If he’s 10 years, it’s $45 million a year for six years. The latter is almost inconceivable to commit to for a pre-free agency deal four years before you have to.

That potential deal would require him to be at least a 4.2 WAR player for 7 years, starting with four years in the future. I don’t know guys. I know he has good projections, but that seems utterly insane. Granted, the real test of the deal will be if, when he would have entered free agency in four years, we think he’d get a better deal on the free agency market. Assuming he doesn’t collapse in four years, and the Padres wanted him at any cost, the deal makes a lot more sense when viewed that way. But still a lot can go wrong.

Who is the most obvious comparison to Tatis Jr. on the Cardinals? Well nobody, but Jack Flaherty might be the closest. Nobody else is really even close. Flaherty is three years older and has one less year of team control, so it’s not perfect, but his projected 4.3 WAR by ZiPS is not too far from Tatis’ Jr. projected 5 WAR. If Dylan Carlson wanted to go out and have a 5 WAR season in 2021, he would be a much better comparison, but until he does that, he’s not even in the conversation.

Flaherty has expressed a desire to go to free agency before. He seems to have no intention of signing an extension before he’s a free agent. Which obviously makes this post less of a possibility and more of a hypothetical. That’s okay. I’ve dealt with hypotheticals this entire offseason. And there has been one thing that has changed - I don’t think it will change his mind so much as put the Cardinals in a better bargaining position.

Prior to 2020, Flaherty looked well-positioned for arbitration, but the short season and the less than great ERA seemed to have put his arbitration number insanely low, at least according to MLB Trade Rumors. They are usually scarily accurate, but the pandemic-shortened season changed things so much, I’m not even sure we can trust their numbers. This entire post hinges on their number, but like I said above, we’re dealing with a hypothetical here. MLB Trade Rumors projects $2.6 million in Flaherty’s first year of arbitration.

This is very low. I’m not necessarily comparing the pitchers, but Jacob deGrom got $4.05 million back in 2017, Noah Syndergaard got $3 million after missing nearly an entire year due to injury (and he was Super Two), and Luis Severino was either going to make $4.4 or $5.5 million before the Yankees signed him to an extension. Viewed in this context, it actually makes sense for Flaherty to get $2.6 million, but after 2019, he was coming off a 4.7 fWAR season and 5.7 bWAR season so it’s clear this is a step down from the pace he was on.

I mention this because Flaherty isn’t really a different pitcher. Arbitration currently views him as a different pitcher. There’s a limit to how much more money he’ll make in arbitration now thanks to how poorly timed his down half-season was. deGrom had a 4.1 fWAR season the next year and his price only rose to $7.4 million (he then signed an extension). Sydnergaard is still making under $10 million for 2021 (thanks to opting out of 2020, but still).

So hypothetically, the Cardinals and Flaherty’s interests momentarily align. Arbitration undervalues him, the Cardinals could remedy that. Cardinals want Flaherty beyond arbitration years, Flaherty might want more certainty now that the ceiling has been lowered for his next three years. I don’t even want to mention the elephant in the room that could keep his arbitration price even lower if he doesn’t sign an extension.

So what does a Flaherty extension look like? Well there’s two things to consider. Flaherty’s projected WAR is 4.3, but his projected salary is quite a bit lower than a first year arb guy who is a 4.3 WAR player would make. In fact, I wonder if MLB Trade Rumors is just wrong and arbitration won’t correct for the fact that two months of play is absurdly affecting Flaherty’s arbitration number here.

Let’s assume they aren’t completely wrong though. $2.6 million might be low, but he’ll still get less than he should (even accounting for the fact that the system is artificially lowering his salary, may I add). If I had to guess, if the $2.6 million is accurate, his next two years of arbitration might go something like this, if he pitches well: $5.5 million, $10 million. If he pitches like a Cy Young contender, it will be higher than that I hope, but projections aren’t really assuming something like that, so I won’t.

So in order to make a deal work with Flaherty, I think you got to exceed the arbitration number here. Like just straight up accept the Cardinals will not be making a “good” deal over the next three years. How much of a not good deal would depend on Flaherty’s performance, but it seems to me very unlikely what he’d get in arbitration would exceed what I will propose. I’m not going to do anything fancy with my numbers here: 5, 10, 15 for his three years of arbitration. He will definitely not make $5 million this year and probably not $10 million next year. $15 million is possible if he pitches absurdly good. Trevor Bauer made $17.5 million, but he also started at $3.55 million in his Super Two year.

Now, we’re at free agency. He’s 28. Now the question is how many free agent years are the Cardinals buying. This is a fairly difficult question actually. I’ll present two different scenarios. The first is the scenario where Flaherty still wants to enter free agency at an acceptable age. The second would make the extension his big contract. With the first, the Cardinals will buy two free agent years and Flaherty can enter free agency at age 30. With the second... well we’ll get to the second.

So buying out two free agent years. I chose two free agent years, because the Cardinals probably wouldn’t guarantee $30 million over the next three years with just one extra year of free agency. And Flaherty being a free agent at 30 instead of 31 is a fairly big difference. IF, and this is a big if, Flaherty could be convinced to sign an extension here, we’re probably looking at five years.

So how do we value Flaherty three years in the future? He’ll still be 28. He’s currently projected for 4.3 WAR by ZiPS. At the same time, an extension doesn’t make much sense if we project him as a 4.3 WAR pitcher at 28. There’s simply too much downside given where Flaherty is currently at. So I’m going to say that an extension would assume he’s a 3.5 WAR pitcher in both his age 28 and 29 seasons. I don’t have access to ZiPS so this is a guess. And because I like round numbers, I end up assuming he’s a bit better than that anyway.

At $9 million per win, the 3.5 WAR version would be worth $63 million over those two years. We’ll round up as I said. And his overall contract, combined with the $30 million, comes out to 5 years, $100 million. The Cardinals don’t have much on the books for 2022, so you can make that really appealing by giving him close to $20 million in 2022 if he wants, which would be a hefty raise from what he’d get in arbitration. Would make him cheaper in his free agent years too.

The other version operates under the assumption that entering free agency at 31 would not produce a large contract, so might as well sign for as many years as you can. There’s really no in between the way I see it. Flaherty could either enter free agency at a relatively young age or he can enter free agency at old age. In between and he ends up being one of those guys who never really got a big contract because of when he became a free agent. So this extension would be his “big contract.”

The projections do not change for this one. Age 28 and 29 are 3.5 WAR. Age 30 will be as well. Once he reaches age 31, I start declining by 0.5 WAR. And I’m going to stop at age 34. In other words, we’re looking at a 10 year deal here. A 10 year deal for a pitcher is a questionable decision, but it’s the kind of questionable decision that would need to be made to lock up a pitcher who needs a good reason to avoid free agency. Also, I’m comparing Flaherty to Tatis Jr. and a double digit in year deal would make the comparison complete.

This would give him 19.5 WAR over the course of those 7 free agent years. At $9 million per win, that’s $175.5 million. Add in the $30 million in arbitration, and that’s $205.5 million. We’ll say $210 million, and he gets a $5.5 million bonus at the start of the 2022 season to make that work. That is an average of $25 million per year.

There are ways to make it look more enticing with bonuses. Give him money for winning the Cy Young, finishing in the Top 5, and finishing with MVP votes. Give him innings bonuses. And lastly, I’ll finish with what I will call the Jon Lester clause. Give him an 11th team option year for $25 million with a $10 million buyout. Which would raise the price of this deal to 10 years, $220 million. The high buyout is a way of guaranteeing and making it possible the Cards actually accept it - 1 year, $15 million for a 35-year-old Flaherty is something they could plausible accept (or rework into another deal)

None of this is realistic. The latter deal, I don’t think anything like that’s ever happened. Anytime a pitcher has signed a deal before free agency, it’s been at significantly discounted price from what I’m proposing. But I’m operating under the assumption that Flaherty needs a reason to avoid free agency and $220 million with the potential for more would be hard to pass up. Maybe. I don’t know. That’s not a decision I can remotely relate to honestly.

I guess the question isn’t: will this happen? We know it wouldn’t. But would you be okay with either/or of those deals?