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Who wins and WHY? Pre-Flashpoint Rip.

http://media.comicvine.com/uploads/10/105954/1987887-jsa66_22_copy_large.jpg

vs

http://media.comicvine.com/uploads/0/40/77485-33031-kang_large.jpg

Kang's more exotic tech has been featured more than Rip's, so he's definitely got better tech feats in general. However, Rip isn't totally helpless in that area-- he was able to imprison the multiversal version of Mr. Mind by reinforcing Skeets' shell with Suspendium on the fly, and he is also the one who built Supernova's suit. Additionally, he is one of the only beings in the DC continuum who can access/understand Hypertime.... Oh and he imprisoned the Linear Men as well.

But yeah, Kang likely wins. Good fight, though.

I think if Rip has his hands full dealing with Per Degaton, Kang will be a nightmare.

Per degaton would give kang a good fight as well. Rip would be a worthy adversary imo. Especially since there are near infinite possibilitiea in a time battle.