Trying to Find a Realistic Jake Arrieta Extension is Not Easy, But I'll Try

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Trying to Find a Realistic Jake Arrieta Extension is Not Easy, But I’ll Try

Chicago Cubs

jake arrieta cubs roadLate night on Friday, the Chicago Cubs and ace Jake Arrieta agreed to a $10.7 million deal for 2016, which avoided the need for an arbitration hearing, which would have come this week. That’s good.

Unsettled still, though, is Arrieta’s price tag for 2017, his final year of arbitration, and what happens thereafter. Free agency looms for a guy who has emerged as one of the best pitchers in baseball. It’s great that the Cubs have him, but it’s likely that they’ll have him for only the next two years.

With that in mind, Bruce Levine makes the argument that now is the time for the Cubs to sign Arrieta to an extension, and he’s unquestionably right that, if it were going to happen, now would be the time to do it. Once you get into the season, it’s not likely to be a primary focus for either side. And then, once you get past the season, Arrieta will be just one year away from free agency – a tough time to get an extension together. Furthermore, there will be another year of performance to look at and potentially complicate things further (if Arrieta’s a stud once again, no extension will happen; if Arrieta underperforms or gets hurt, coming to an agreement could be really tough). Now is the time.

… howeva, as I wrote last week, I just have a very hard time seeing a realistic deal coming together for both sides.

Levine proposes a four-year deal with two option years thereafter for the Cubs, with $85 to $90 million guaranteed to Arrieta, and then $25 million per year on the team options. Here, we run into the problem to which I always point when this topic comes up: that’s a deal the Cubs are probably willing to sign, but would Arrieta? To beat that offer, Arrieta need only make, say, $15 million in arbitration next year and then secure a free agent contract worth more than $70 million. Yes, it’s absolutely possible that he could not get there – we’ve seen it happen before – but it’s also quite possible, given how damn good he looks, and how the market has moved, that he could land a free agent deal worth three times that amount.

Maybe Arrieta’s the kind of guy who just wants that life-changing security (though I’d argue with more than $15 million now in career earnings, he might feel plenty comfortable now taking his swing and betting on himself). Maybe the sides can get a deal like that done – I don’t think going too much higher than that, from the Cubs’ perspective, is going to make sense, given the two years of remaining club control at ages 30 and 31.

Having said that, I get the urge to at least try and see if I could find the middle ground – the spot where it would make sense for Arrieta to accept the deal, and it would make sense for the Cubs to put it on the books today.

Perhaps if you play with Levine’s proposal, add one more guaranteed year, play with the salaries a bit, thus bumping up the total guarantee quite a bit? So, something like:

2016: $10.7 million (age 30) (arb 2 year)
2017: $15 million (31) (arb 3 year)
2018: $25 million (32)
2019: $25 million (33)
2020: $25 million (34)
2021: $25 million club option, $10 million buyout (35)

So you’ve got a $111 million guarantee over five years, including the two arbitration years. The three free agent years come in at just over $28 million AAV if the option in 2021 is not exercised and Arrieta gets the buyout.

The Cubs, then, get what amounts to a $15 million option year in 2021. For his part, Arrieta gets near free agent-level dollars for three free agent seasons.

(As a very quick and dirty cross check: Arrieta is projected for about 5.0 WAR in 2016, and, if you grant him that, and decline him by 0.5 WAR each year thereafter, he’d be worth 20 WAR over the next five years. At $8 million per win on the free agent market, that’s $160 million. But because he’d make only about $25 million via arbitration the next two years, during which time his value is $76 million, you’ve got to lop off the difference. That leaves you with $109 million guaranteed over five years, though it would actually be a little bit higher when you account for WAR/$ inflation. I swear I didn’t even do that math until after I’d laid out the payment schedule above. Pretty incredible how close it is.)

So then, would Arrieta do that deal? Would the Cubs? Should the Cubs?

I don’t think we can answer the first question, at least not as phrased, since we don’t know Arrieta’s personal motivations. We can say that, given his relatively short track record of elite success and his age, it wouldn’t be a bad deal for him by any stretch. Yes, it’s less than Zack Greinke and David Price got in free agency this year, but Arrieta would be booking his money two years away from free agency. Still, it feels light.

As for questions two and three, it’s a tough call. On the one hand, it looks like a nice deal for the Cubs, and they’re going to need the pitching going forward. Further, we believe their revenues are only going to increase over the next couple years before really exploding with the new TV deal. On the other hand, in that proposal, Arrieta’s biggest money would be kicking in right at the same time that the Cubs’ young core will be going through arbitration and getting (hopefully) really expensive.

I do think Arrieta’s a good bet to age well, though he hasn’t yet gotten past the point where the velocity noticeably dips and he proves he can still be highly effective. His conditioning, intelligence, precision, stuff, and wide repertoire suggest he can be that guy, but it’s dicey to commit a ton of money before you know for sure. Then again, Arrieta’s velocity was actually up last year, so maybe he won’t even face the velocity dip for a few more years – he could be delightfully abnormal in that regard.

At the end of this, all I can really say for sure is that it’s difficult to find that middle ground where a long-term deal makes sense for both sides. The Cubs are creative, so maybe there are other structures – opt-outs, options, incentives, etc. – that could make it work, but I’m doubtful. For now, I’m steeling myself against Arrieta’s expected departure in two seasons. Here’s hoping he’s fantastic with the Cubs in that time, and earns himself an enormous payday.

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Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.