The previous volume of Deadpool ended because of Secret Wars. Because the Avengers, as written by Jonathan Hickman, are useless and didn't fix the Incursion mess. The book was naturally immediately restarted, and Duggan took the opportunity to make Deadpool massively popular in-universe, becoming a pop culture and merchandising sensation.
Popular enough to franchise his likeness and hire 4th tier characters like those schmucks up there to dress up like as act as the "Mercs for Money" (Murdock sued him on behalf of Luke Cage to prevent the use of "Heroes for Hire"). Popular enough to bankroll Old Man Steve Rogers' Unity Squad Avengers team. The funny thing is this run actually started about 4 months before the first Deadpool movie came out.
The first 35 issues of this run are Wade starting out at the absolute best place he's ever been, and then steadily losing it all. His mercs grow increasingly angry with him as he stiffs them on their paychecks. Which he's doing because Avengers are expensive, and Wade, trying to live up to Captain America's belief in him, is throwing every cent he's got into the team.
The sad thing about the run is, Deadpool is trying really hard to actually be a hero, be an Avenger, be better, and fails completely. His mercs leave, his wife gets frustrated and starts taking other lovers. And, you know, declaring war on the surface world. He loses track of Michael the necromancer and Ben Franklin's ghost until he needs them for a tie-in to a Dr. Strange event, then loses both of them. He tried to reach out to Madcap, who he thought was alone and sad, but it's too late. The damage Wade did in the past was too much.
The high point of this portion of the run is the Civil War II
tie-ins, surprisingly. Because Duggan and Hawthorne just take the piss
on the entire stupid thing. Every issue is Wade getting into some
pointless fight that could have been resolved if people had just talked
about it reasonably. And it gives us Wade dropping the Macho Man flying elbow
on the Black Panther, and them hitting each other with toilets.
And then, of course, there was that whole thing where a sentient Cosmic Cube somehow got used to make it so Steve Rogers was always loyal to HYDRA. By the time Wade realizes things are wrong and he shouldn't trust Captain America, he's in too deep, and everyone's using him as Example #1 of how they should have known something was wrong with Rogers all along.
(Just for the record, the Cosmic Cube thing was Maria Hill's fault, as she'd tried to use it to alter villains' minds, and it got turned around on the heroes. She's the worst. Even Gyrich doesn't fuck things up as spectacularly as she does.)
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