I had to ask the question: In a fight who would win, Punisher or Deadpool? In my opinion, Deadpool would skunk the Punisher. I know that the Punisher is a well-trained warrior but Deadpool has ninja skills and a healing factor! On top of that Deadpool is completely crazy. I've done some checking on the internet and found out that they did fight in Deadpool #54 and #55. Apparently in that fight Punisher won. The truth is that in my mind no way such a thing could happen. I decided to stage a fight in mugen. ApoCalypSe's Punisher vs the Unlimited Deadpool - each under computer control.
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Keep in mind that Deadpool is sloppy and unpolished, he's world class for sure, but his healing factor has carried him much further than his abilities as a combatant or a tactician. He certainly does some ninja work, but he is no Electra either. Most likely, I'd say frank would detonate ol' wade. He certainly can't kill our favorite merc, but frank's ruthless efficiency should prove out against wades bat-shit-storm.
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