Wolverine might be a skilled fighter and tactician but when it comes making a plan only Deadpool can come up with the truly crazy ideas.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 Romuluss heir. Wolverine of course is against the plan and seeks it to stop Romulus by beating him instead.
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 Braith waite Ruby is approached by Romulus and sells Wolverine out. Knowing that Romulus has studied Wolverine his whole life Logan knows his plan isnt 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 dont think of Deadpool as an accomplished strategist. Mainly because hes not. He doesnt 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 and in doing so completely throws his opponents off guard.
Another benefit to this is that Romulus has been tracking Wolverine his entire life. Its no secret that Wolverine is not a fan of Deadpool. Logan is not shy about telling people how much he hates Wade. So Romulus would never expect Wolverine to actually go to Deadpool for help. This is the unexpected maneuver Wolverine needs to get out in front of Romulus in order to beat him. It also shows just how desperate Wolverine is to win if hes willing to resort to teaming with somebody as unstable as Deadpool. So despite how much Logan cant stand Wade Wolverine does at least respect Deadpool enough to come up with a worthwhile albeit bonkers plan.