If he thinks he can get the Jazz to trade him before the season starts, he won't miss out on any money. I guess it could ding his reputation a bit, but how much really? Many established players have publicly forced their way off of teams and did it really hurt them all that much?
And the Jazz have already crossed a similar line several times before, when they traded Deron and Donovan supposedly because they thought they would not re-sign with the team. If it is true that Bailey doesn't want to be here, then I don't see how this situation is all that different from those two. And to think that NBA teams are going to circle the wagons in support of the Jazz? LOL, if any other teams think Bailey can play and be had at the disadvantage to the Jazz, they will be happy to make offers.
If Bailey told the Jazz straight up not to pick him and the Jazz ignored that, it seems plausible to me he could really try to force his way out.