As a gamble, it was absolutely the right one to take, but I would say 'no' if he walks, and we don't win a championship this year.
Hayward would still be here, and likely an all-star (although that's not really fair to say), we would have had a good draft pick, Crowder, and I very much doubt IT would be here - nevermind being paid $15M/yr. We had the option to sign him this past off-season for the minimum and we passed - why would it be any different if he were an expiring with us?
Anyway, you make deals for star players so they can grow with your team and help you win championships - Kyrie wasn't even on our playoff roster last year. I definitely hope we re-sign him and he is a big part of our future, but I see no reason to say 'yes' to this question.