10 Worst Things That Ever Happened To Wolverine
5. The Punisher Humiliates Him - Punisher #16-17
Wolverine should be able to easily take any spec ops operative, even if that operative happens to the Punisher.
This fact makes it all the more humiliating then, when Frank swiftly defeats Logan and hands him one remarkably brutal beating that must easily be one of the most painful the mutant has ever suffered.
The interaction begins with Castle shooting Wolverine in the face with a shotgun - and only gets worse for the X-Man as it progresses: he gets shot in the crotch, left behind in a warehouse full of criminals, and THEN Punisher runs him over with a steamroller.
The mix of gore and dark comedy was obviously a byproduct of Garth Ennis' dislike of superheroes, but it's still one of the worst things Wolverine's ever had to suffer through all the same.