Deadpool can't be killed... Unless he somehow sent him somewhere in to space/froze him to the core he couldn't really win.
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That's kinda what I'm saying. There are ways to eliminate deadpool without killing him. Such as locking him in a perpetual state of drowning, freezing him, putting him in a situation where he is damaged as fast as he regenerates etc. Plus, chief has promethean weapons that digitize there targets, literally putting them into a cyber mainframe. That could do it. As I said before though, deadpool would probably win, it's just a lot closer than people think