OK GSP will never beat Chuck I don't care what anyone says GSP's striking is not as good as people think it is. He doesn't have enough power behind his punches to knock ANYONE out. Hell if I was his size I would love to have a kickboxing match with him. He is not that impressive IMO. I think I could take him in kickboxing (If I was bigger lol).
As for MW, that is a different story. I think Rich would beat him, and maybe even Marquardt and Mike Swick. Silva is 50/50 for me. If GSP can take him down he might be able to pound him out, but if he wants to try and stand and trade with him, he will be leaving on a stretcher. GSP has very good takedowns and very good wrestling on the ground but his standup is kind of subpar. He could be good if he learned how to punch with some more power. I mean the guy is massive he should be KOing people left and right but he has 0 KO's on his record. That tells me he doesn't know the proper way to punch quite yet. But he's only 25 so I'm not saying he will never learn.
We'll have to see what happens at WW before we get all giddy about this though. He should have no problem with Serra, but I personally believe Diego, Penn, and possibly even Hughes stand a fantastic chance at beating him and taking his belt. Not too long and Fitch may be able to take him also.
If he faught Chuck 10 times I think GSP would win once. Chuck is waaaaaaaaaaay above him in many aspects. If Tito and Couture had trouble taking Chuck down, GSP doesn't stand a chance. And there's no way he is on Chuck's level in the striking department.