The way I kind of look at contracts like this is as follows:
Does the contract make the player more tradeable or less? I am not implying that the Indians will/would trade him, but I think we can universally agree that the terms of the deal clearly make him more tradeable. Therefore, regardless of whether the Indians cash in on this "equity" with a trade or not, the bottom line is that they have improved the overall value of their team.
I am impressed with the Dolan's resigning Jake, and I am unworried about the Dolan's resigning CC. If CC finally puts together a dominating couple of seasons, then the Indians will be unable to resign him anyway at (18-20 million per year). If he does not put together a real "ace" year, then he will be too expensive for what he is really worth.
I personally, don't care if the Indians resign him. I think he is a great pitcher, but still is just short of ace. Will he ever be a true Ace? I am not sure, but based on his "conditioning" and other aspects, I am unsure, but he does have "ace stuff." Personally, I think he will be a career underachiever (which will still be pretty impressive).

