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Enishi runs around the ring for 15 minutes until Shishio explodes
Enishi lost to a straight one-on-one duel against Kenshin. Shishio got quadruple-teamed by Kenshin, Aoshi, Sato and Sano and technically *still* didn't lose, only being defeated by running out the clock. You do the math.
Ehhh, to be fair, Saitoh did get his legs almost completely wrekt by Usui. Sure, he still had a lot of power, but he definitely wasn't even at 50 percent of his max thrust for his Gatotsu.
Sano was hit by multiple blows that vaporizes boulders and while he did receive treatment, it was basically just some ointment. Dude probably had massive internal damage.
Aoshi got completely bodied by Kenshin's ougi and couldn't even hold his sword in a previous scene. And he lost most of his speed.
Kenshin got slashed multiple times all over his body (including one giant gash on his back), Aoshi took his sweet time pummeling him with his fists (which are stronger than Sano's minus Futae no Kiwami) and the guy performed two ougi's, both of which place enormous strain on his body.
None of this is to say that Shishio wouldn't have won against each person, but he certainly wouldn't have made sport of them the way he did.
As for Enishi... well, Enishi was fast enough to blitz Kenshin in one scene and was able to more or less counter Ken's best techniques. And unlike Ken, he has a real sword. So he definitely would just kill Shishio.
Buuuuuuuuuuut, Shishio isn't just someone you beat by being faster than him. He clearly can handle fast techniques like the ougi and a point blank range Gatotsu.
Shishio, probably 65/100
Guy And Chou's RPG Site
Rumbles Moderator
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If this was the manga versions, I would give Enishi a moderately easy victory as he's basically someone with base stats and skills comparable to Kenshin's (to say nothing if his Nerves of Insanity that give him notably better reflexes than Kenshin's come into play) and the willingness to kill (especially since his swords don't even HAVE a blunt side), and Shishio only survived against even a very worn out Kenshin only because Kenshin's reverse sword prevented all the hits he had landed from killing/dismembering him. Like, at one point in their duel Shishio took a chain of Ryu Kan Sen attacks that would have probably instantly killed him at least 3 times over if Kenshin had just flipped his sword around.
I can't say about the live action versions, though, but if Kenshin had to fight a similar gauntlet before getting to Shishio and Enishi had been able to match or beat a relatively fresh Kenshin, then I guess the same general principle would apply.