I’m not sure if you have heard or not, but Jake Arrieta will likely become a free agent after the 2017 MLB season.

The last week-and-a-half has been the climatic carryover of the offseason in which the Chicago Cubs and Jake Arrieta were reportedly far apart on a long term extension.

In case you missed it, the reason for this ramp up in Arrieta contract talk (or lack thereof) is the unexpected contract-extension of Stephen Strasburg in DC.  The article linked is a great piece on how that move has effectively demoralized any team hoping to wait out this trade deadline and look to sign a front-end starter long term this offseason. Nope, not happening now.  The trade deadline will be absolutely dominated by potential controllable arms being shopped around from teams a few years away trying to find the highest bidder amongst teams looking to compete the next 2-3 seasons.

Therein which we find the Jake Arrieta conundrum.

I wrote a piece about a week ago(before all these national pieces, mind you) about how the Cubs will likely utilize their wealth of controllable offensive talent for trades as much as they do for on-field product as a way to hedge against Jake Arrieta’s free agency.

I will once again reiterate my absolute infatuation with Jake Arrieta along with my belief that he will be a rare pitcher to perform extremely well into his mid-30’s.

That said, the Cubs cannot and will not be signing him to a 6-7 year contract following the 2017 season. It just wont happen. Save this article and absolutely blast me for it 2 years from now if it happens. I’m that confident.

On the flip-side, Jake Arrieta will not be signing a contract that is LESS THAN 6-7 years. Won’t happen. He deserves that money. Ridiculously uninformed Stephen A Smith comments aside, Jake Arrieta has been the hardest worker in baseball for years. He is meticulous in taking care of his body and health. If he were not a professional baseball player then he would be winning iron man contests. He is what most human beings strive to be in terms of physical health. He deserves every stinking cent and every freaking year of a contract he will inevitably command.

Had the Jake Arrieta situation been presenting itself just 2 seasons earlier, I would not be writing this article. Timing would match up quite perfectly with Jake Arrieta in that hypothetical situation and the Cubs and Arrieta would very likely find common ground on a long-term contract.

It didn’t happen that way, however. So I am going to present to Cubs fans a very unpopular case that is no doubt being reviewed by the Cubs executive brass frequently when discussing Jake and why Jake Arrieta will not be a Cub  past 2017. Which is just more of a reason to enjoy his greatness now.

I present into evidence- “The Kids”:


Awww. Aren’t they cute. Back when they were everyone’s sweet, little prospects all of 1 year ago. Now, for the most part, they have destroyed enough pitchers fastballs that you can see the seams running scared off of the baseball when a pitcher is going into their wind-up and the ball suddenly realizes that Kris Bryant is up to bat.

These guys, along with Anthony Rizzo and Javier Baez, will be coming up on their big payday all within 2 seasons of each other. Here’s how it looks:

Kris Bryant– Last year of arbitration is 2021.

Kyle Schwarber– Last year of arbitration 2021

Addison Russell– Last year of arbitration 2021

Jorge Soler– Current contract last year 2020(though he can opt-in to arbitration before then)

Javier Baez– Last year of arbitration 2021

Kyle Hendricks– Last year of arbitration 2020

Anthony Rizzo– Last year of contract(including team options) 2021

You see a little trend happening here? This, again, goes to the point I made in that previous article that the Cubs will no doubt be looking to move some of their controllable ML ready surplus talent for other needs. Mainly, a controllable arm that matches up with the obvious window of now through 2021.

Additionally, I enter into evidence- “The Contracts”:


Now let’s look at the high-dollar contracts the Cubs currently have and when they fall off the books:

Jon Lester– Last Contract Year 2021

Jason Heyward– Able to opt-out following 2018 or 2019(barring a dramatic instance- as long as Cubs win a series- he will likely opt-out)

John Lackey– Last Contract Year- 2017

Jason Hammel– Last Contract Year 2017(assuming option picked up)

Ben Zobrist– Last Contract Year 2019

So, assuming all of these players are gone by 2021(when the kids will be reaching their longterm contracts) let’s look at how much money will be freed up:

89 million AAV (average annual value) will be freed up by then. Whew, THANK GOD! Because when you look at the list of players that will be coming up for major contracts at that time, the Cubs are going to need every single penny of that 89 million PLUS whatever is coming in from their lucrative TV deal.

They won’t resign all of their players, no. However, if we are banking on the cornerstones being Kris Bryant, Anthony Rizzo, and Addison Russell then you are talking about roughly 650 million combined between the 3 of them. That is NOT an overstatement. In fact, it is quite likely an underestimate.

So what happens if we sign Jake Arrieta to a 6 year contract following 2017? Let’s be nice and say it’s 6 years and 210 million(though with inflation it will likely be more).

That cuts into more than one-third of the 89 million of AAV being freed up over the next few years. It’s not the money or HIS age that makes it nearly impossible for the Cubs to sign Jake Arrieta. It is the timing in which his contract will be signed and the timing of the core of our franchise.

Serious question: Who do you want to give up in 2021 to keep Jake Arrieta through 2023-2024? Is it Rizzo? Bryant? Russell?

Lastly, I present as Evidence- “The Potential Arms”:051015-MLB-Indians-Danny-Salazar-pi-ssm.vresize.1200.675.high.57.jpg

I don’t want any of those players gone. They are the cornerstones. Instead, what makes sense for the Cubs is using their current crop of controllable talent that are not necessarily the cornerstones to acquire a frontline pitcher that is either cost-controlled or has a contract which better matches up with the Cubs current window of this season through 2021 with financial flexibility.


So, in examining that specific criteria you come away with quite a few names:

Danny Salazar– last year of arbitration 2020

Carlos Carrasco– Team options through 2020

Sonny Gray– Arbitration eligible through 2019

Chris Archer– Team options through 2021

Jake Odorizzi– Arbitration through 2019

There are others, too. This is a nice list to get started with. However, the point is to be sure that our window is wide enough to get as many opportunities at a World Series as possible during the time that our “Kids” are cost-controlled. That is the point of the exercise. Theo Epstein has said as much..

Once the kids become expensive the conventional thought-process is that the cost-controlled players will flip from being heavy on the offensive side to being heavy on the pitchers mound.

Once Russell, Rizzo, and Bryant all sign their long term deals,  the Cubs should have some very nice pitchers hitting or about to hit their full stride in the bigs. In Dylan Cease, Oscar De La Cruz, Bryan Hudson, Justin Steele, and Duane Underwood, the Cubs will have pitchers with varying levels of impact and cost-control contributing at the major league level on teams competing for championships. As you can see its a very similar model to the current Cubs offensive cost-controlled crop, except for the cost-controlled “type” of player has been flip-flopped.(pitchers as opposed to hitters).

So there it is. I love Jake Arrieta and will treasure all of his starts over the next two seasons. However, it just doesn’t make sense to sign him long-term. The length of time the contract would take just doesn’t add up. “The Jake Arrieta conundrum.”

Oh, what a wonderful problem for a franchise to have.