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A Jack Flaherty Extension: Take 2

Two years ago today, I looked at what a Jack Flaherty extension would look like after his amazing second half of the 2019 season. I've done some individual work on contract values since then and Jack Flaherty has not quite lived up to what he was in the second half of 2019 since then, but is also closer to free agency and already in arbitration. What would a fair extension look like in today's world?

First, let's look at what I had last time as a guideline, keeping in mind we would be two years into this deal already, with the cheapest seasons having expired.

5/$60M guaranteed

6/$88M with one mutual option used

7/$116M with two mutual options used

8/$140M with one club option used

9/$160M with two club options used

10/$178M with all three club options used

I am going to set out some parameters here. First, for arbitration, I always like to look at the 25/40/62 rule to project those seasons' salary numbers. Last season in arbitration, Flaherty was able to eek out $3.9M from the Cardinals. That would be approximately 25% of his open market value since that was his first arbitration season. Meaning, if he was on the same path now that he was then, he'd be worth approximately $15.6M on the open market. Now, since then we have had a season in which Flaherty got hurt but was still able to be worth 0.6 bWAR and 0.9 fWAR in just 78 1/3 innings pitched. Feeling comfortable that Flaherty could bounce back to 150 innings would make him worth between 1.1 to 1.7 WAR and feeling comfortable giving Flaherty 180 innings instead would make him worth between 1.4 to 2.1 WAR.

That's just using the 2021 season as the bar, though. Instead of using two totals, I'm going to average out Baseball Reference's bWAR and Fangraphs' fWAR from here on out to estimate WAR. Over the last two seasons, Flaherty has been worth 0.9 WAR in 118 2/3 innings. That prorates to 1.1 WAR per 150 or 1.4 WAR per 180. Over the past three seasons, he's been worth 2.8 WAR per 150 or 3.4 WAR per 180. For his entire career, the two marks are 2.6 WAR per 150 and 3.1 WAR per 180.

I'm going to be very pro-player here because I still think my dollars per WAR values I've been working with are pro-owner because I tried to go off of what's been done in the past - which has been quite pro-owner. So hopefully my pro-player approach with a pro-owner algorithm will balance this out to be a fair deal. I am going to assume a fully healthy Flaherty pitching semi-well. That's a 3.25 WAR pitcher to begin this exercise. With Flaherty entering his prime still at 26 years old, I think the following WAR totals are quite possible:

arbitration season 2 - 2022 (age 26): 3.25 WAR (at 40% of his market value)

arbitration season 3 - 2023 (age 27): 3.5 WAR (at 62% of his market value)

free agency season 1 - 2024 (age 28): 3.5 WAR

free agency season 2 - 2025 (age 29): 3.5 WAR

free agency season 3 - 2026 (age 30): 3.25 WAR

free agency season 4 - 2027 (age 31): 3 WAR

free agency season 5 - 2028 (age 32): 2.75 WAR

Historical examples of 3-3.5 WAR players signing long term deals include the following table of players. The 3 WAR players averaged out to earning about $14M a season and the 3.5 WAR players averaged out to earning about $18M a season. That's $4.65M/WAR for the 3 WAR players and $5.15M/WAR for the 3.5 WAR players.

Using that historical data, we'll say that he'd get around $16M a season on the open market at the moment for 2022. I will say that at this point, using those numbers, I don't think Flaherty would chance signing an extension right now until he re-establishes a value closer to what it was after 2019. For the sake of him and the Cardinals' 2022 hopes, I really wish Flaherty well in doing so. He's not going to bet low on himself. On to the contract.

For Flaherty's contract, I will be using the following constraints:

  1. He will make 40% of his value in 2022 and 62% of his value in 2023. He will make 100% of his value beyond that. This is due to the current arbitration system that might change in the new CBA.

  2. Assumption is that he increases in value by 0.25 WAR after this season, but decreases by 0.25 WAR at ages 30, 31, and 32.

  3. The original price of approximately $5M/WAR will hold true for 2022 and that it increases by 5% inflation each offseason thereafter.

A Jack Flaherty extension under these conditions would be quite team friendly, as I suspected.

You can see the different offers that I would make him currently. The first two years eat up his arbitration. The last 5 years are different contract lengths that would eat into his free agency.

I would offer him $6.4M in arbitration for 2022 and $11.2M in arbitration for 2023. Any extension I offer him would eat up at least one year of Free Agency, so the following contract offers are based on eating 1 through 5 years of Free Agency.

3 year deal worth $36.6M. ($12.2M per season)

4 year deal worth $56.6M. ($14.15M per season)

5 year deal worth $76M. ($15.2M per season)

6 year deal worth $94.9M. ($15.82M per season)

7 year deal worth $113M. (#16.14M per season)

Like I said. If I'm Jack Flaherty's camp, I'm not impressed with those numbers and I walk away. That's a slightly worse deal than what I found for him last time I did this two years ago and this time I'm buying out 2 years of pre-arbitration and arbitration rather than 4 - which kept those contracts down. If I'm the Cardinals and this is what my projections for him would warrant, I do not even take these numbers to him and risk him wanting to walk away at the end of the contract.


Nick Childress cover art! Thanks!

Historical examples:


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