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Who is deadpools arch enemy?

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But to go ahead and answer you question, in his first run, I would say T-Ray. Now it doesn't really seem like he has one. Maybe Agent-X to a degree or even Norman Osborne.

Wolverine

Galactus

Aunt May

It is either clowns or mimes ... or T-Ray who is actually Wade Wilson. So deadpool worst enemy is himself.

logan.