In the Marvel Universe, Wolverine claims to be the best there is and what he does. But when it comes to being unpredictable, he has to defer to Deadpool instead.
For a long time in his various Marvel Comics stories, Wolverine walked around as a man without a memory of his past or where he came from. When he eventually gets his memories back, he goes in search of his roots. He discovers that a mysterious and ancient figure named Romulus has been manipulating him for most of his life. Romulus hopes to have Wolverine and his son Daken battle to become Romulus's heir. Wolverine, of course, is against the plan and seeks it to stop Romulus by beating him instead.
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To do this, Wolverine puts together a team that he thinks will be good against Romulus. However, one of the team members is Ruby Thursday, and in Wolverine: Origins #45 by Daniel Way and Doug Braithwaite, Ruby is approached by Romulus and sells Wolverine out. Knowing that Romulus has studied Wolverine his whole life, Logan knows his plan isn't bound to work. So he has a backup devised by one of the most unlikely people anyone would think Wolverine would ever approach in such a dire situation: Deadpool.
Fans don't think of Deadpool as an accomplished strategist. Mainly because he's not. He doesn't understand the concept of strategy and tactics like Captain America. But one thing Deadpool does have is a mind prone to insanity. Because he tends to think in a way nobody else does, the Merc with a Mouth is able to come up with plans and ideas that are so ridiculous they are impossible to predict. Deadpool does things that are completely illogical for reasons a sane person would never imagine
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