Jake's upcoming fight with Dan Henderson could be his last with StrikeForce. He will essentially be a free agent win or lose. If he wins and Dana White grabs him for the UFC, do you think he has a shot with Silva or GSP? Personally I think Henderson will be too big and strong for Shields at 185 and an ugly loss will force Shields back to a buck seventy. So any chance with GSP? Do you want to see it?
Hell no. I actually think that Hendo will wreck him. Shields standup is horrible and none of those guys are a slouch on the ground either. I think any of those guys would eventually catch him.
Bob is right. For one, Shields will get manhandled by Henderson. If he goes to the UFC at 170 he will be a good matchup for many at WW but as far as GSP, No. Shields is a wrestler/BJJ guy with almost zero standup. Penn is a better BJJ guy than Shields and could do nothing against GSP. I honestly don't think there is another fighter in the world at 170 that is in GSP's class.
Shields is definitely getting wrecked by Hendo. It shouldn't hurt his standings at 170 though, and the UFC will probably sign him since he's one of not that many "Name" fighters they have.