I think Kyrie is better than IT4 but it's close. When you factor in age, it's an easy decision. Kyrie is much easier to build around too. I'm also guessing in the fantasy land that Kyrie was traded to Boston, Cleveland would prefer Smart over Morris. Smart would probably start.
Would the C's max Kyrie when he's up for FA if that were to happen though? Can they really afford it luxury tax wise? I think Kyrie stays in Cleveland. There is too much money to be made on the supermax. Does he really value being #1 over millions of dollars?
Sure, unless he regressed why not? It's just a standard max, and it starts the year Horford is on his PO, so it at most overlaps 1 year there, then replaces it in your long term planning (plus you won't be paying IT anything). Plus you'll have a nice staggering effect of deals across your major players (Hayward, Kyrie, Brown?, Tatum, 2018 picks etc.). so you could possibly go through at least Hayward's deal, maybe longer without ever hitting the repeater tax.
On Kyrie, the supermax is attractive, but All-NBA is super tight at the guard spot. (Curry, Westbrook, Harden) and being on a team w/ LeBron dominating the ballhandling opportunities makes it hard to be confident that you'll be eligible for the extension. Also being THE GUY probably helps his next shoe deal, so money isn't a huge issue.
I get the criticisms of Kyrie, but also remember, LeBron is a FA next year, most people think he's going to leave, the team just went through the most important part of the offseason without a GM because their owner is an incompetent. CLE is really only an attractive place to be for at most 1 more season. Without knowing for sure what the biggest vs, smaller issues informing Kyrie's trade desire, I'm not going to kill him for wanting to get out before this season, which is sure to be a mess w/ LeBron spending the whole time dangling a move elsewhere.