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I'm going with Conner here, as the apple of Eden will allow him weaken Issei's mind and create illusions of himself in order to make the battle harder.
 
You are putting a high school student against a trained assissin.

I ain't even mad, that's amazing.

As for my vote, Connor due to better training and and actual skill in killing.
 
Actually, why Issei has even a key without the boosted gear? I mean is like (forgive the redundancy) a Iron Man but without his armor or Ryuko Matoi at the beginning of the series.

It's not that Issei is a very special wall level character.
 
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