It's a great fight. You are supposing he loses. The punisher may in fact win this one.

No, it will show that he is beatable (although his loss to Quintana should already do that) and possibly make him more marketable. If you are right and he loses, he will have lost to a top fighter, ring rust or not.

The reverse is true. If he handidly beats Winky, will other fighters really line up to fight him?

Outside of the welterweight division, which he supposedly left, who is ducking Williams? Dzinzurik offered to fight him. He just fought for a junior middleweight belt. Maybe Vernon Forrest is ducking him? Sergio Mora ducks everybody (see Jermain Taylor duck).