There are no "winners" here. I cannot imagine Orton paying back $3M for the "right" to retire, nor do I see the Cowboys getting a player worth having if his head is not into playing.
I imagine they are waiting it out to see if he reports, but even if he does, why would you want a player who does not want to play? And pay him for it?
Honestly, he is the one who decides. There is no way the team comes out on top unless he does something that practically nobody would do.
In a lot of ways Dallas has already won.
They picked up Weeden for peanuts as the back up.
They've let Orton twist and he either shows, gets fined and starts losing money or retires and pays back some money freeing up a significant amount of cap space.
Dallas paid Orton for a situation like last year and he wasn't good enough to do the job.
They'd probably love to see him retire.
In a game of chicken Dallas wins. Orton has to spend the TC/pre-season as a Cowboy or retire.
They've got no reason to cut him before those labors.
Football is a hard, hard game and if you're head isn't in it you almost have to walk away.
I am sure Orton would like a Waters situation where he could join a team after camp as a back up but that isn't Dallas.
He probably could find that situation with a contender but he'd have to pay Dallas back some cash first and likely only gets the vet minimum wherever he goes.