I'd still do the deal. I suspect he would change his mind if he and Kyrie like playing under Platt and suddenly are making a run for top 3 team in the East.
Not a chance he'd re-sign. Losing culture, bad owner, selfish players. Deng is a class act and he couldn't turn that locker room around. They had to go overseas to get a coach, Gilbert's letter to LBJ, Picking Waiters, picking Bennett, firing Brown twice, etc., etc.
The quintessence of a clusterfest and everyone in the NBA knows it.
Dan Gilbert is not a bad owner at all. He has a lot of money, isn't afraid to spend it, and wants to win. He is probably a bit too involved in the basketball side of things, but he will learn and tone it down a bit. It is also silly to say the Cavs have a losing culture. I mean they are only 5 years removed from consistent 60 win seasons. I mean did Boston and Chicago have losing cultures because they had some lean seasons when their superstars left the team. Now maybe they have losing seasons because they have some selfish players that won't change or maybe they just need a leader (who also happens to be a great player) to get them where they need to be. Some young guys grow up and become what their talent should be (like Zach Randolph) and sometimes they don't.
If you put Kevin Love on the team from last year, I think they are solid mid-level playoff team next season, with the chance to make some noise in the playoffs.
Also, Cleveland is a very nice city. No pollution, no traffic, enough to do, and the lake is awesome in the summer.