Well, I don't believe for a second Neely, Chia, even Claude (who has referred to someone else getting the captaincy only when Chara RETIRES...not traded or anything) thought Chara wouldn't be a God at 39. The loyalty this organization has for Chara is at Bourque level; only difference is Chara is not on a cap-friendly deal (yes, I know there was no cap when Bourque was here, but he always took deals way below market value).
You're right, I don't know they could have gotten something better. But, I would bet they could have. Chara was in the driver's seat and told the team he wouldn't negotiate during the season. Almost immediately after, a deal was signed. The FO was fawning (at least partially justifiable, at the time) over him at the time, and offered him a deal to the age of 42. What I've said is I would have been more satisfied with a higher cap hit at shorter term....don't know if the FO tried that, but that's what I wanted. A contract for a 6'9" D-man until age 42 (a contract which is basically immovable with three years remaining...don't really get why that's 'A-OK' with some of you) is a bad idea. Bad idea then, bad idea now. I didn't like it from the beginning.
It would be one thing if people were arguing from the beginning that "welp, you got to sacrifice some years on the back end for success now", but that wasn't it. People genuinely were (and some still are) penciling Chara in for the #1 D-spot in 2018. That's what really concerns me. We've become so complacent, habitual, and obsessed with one player's past contributions, as a fanbase, that plenty of people don't even want to evaluate the realities of his game. There is no other player in the history of my being a fan (granted, I've only been a fan for about 20 years) that has gotten so many passes and excuses. People seem to be genuinely afraid of admitting what is obvious and moving on. And I, for one, really don't want to suffer through three more years of the same old excuse-making, ignorant comments that we've listened to for the past 2+ years.