The tax threshold combined with some projections of arbitration values for Bryant, Russell, Schwarber, Baez, Contreras and possibly Almora in 2020-21. And holding onto Kyle Hendricks.

My back-of-the-napkin math suggests the Cubs may have just one big free-agent signing available to get through that period (two, if Heyward opts-out).

If Jake comes out as 2nd half 2015 Jake, I could see the Cubs being reassured that the mechanics issues was sorted and – if the market complied to drive down overall costs – perhaps he finally would take a 5 year contract.

I don’t see why the Cubs would opt for a Heyward-like contract if my understanding is correct that only JeyHey has the opt out and not the Cubs. Assuming Jake tanks, why would the Cubs sign a long term obligation saddled with “bad Jake” in late years, but miss out “best Jake” where Boras would be sure to pull the trigger for a higher payday?

In Jason’s case, the Cubs actually neutered the Cardinals, and based the obligation on an annual 3.2 WAR (if I recall correctly) that seemed imminently doable considering his past 4 years of performance with the Braves and the Missouri River Hicks. We had no outfield defense and if we got lucky with 2012 Heyward all the better. Little downside since the defense shouldn’t significantly dip until the last year or two of the contract.

Jake however -being a risky pitcher – can’t offer a baseline that I can see.

I love your idea that the market may help Jake/Scott to rethink the years. Other than (God forbid) injury or meltdown I’m not sure I see any scenario for Jake to remain a Cub, given the model the Cubs set forth. Jake is not Lackey or Lester in consistency and I’d think Cueto would be a much better option if the Cubs were going to do another “Lester-like” contract.

But then again, maybe I’m just lowering my expectations to make the separation less painful…lol