It really depends. If something stupid happens like getting eliminated off an RKO or a LeBell lock (sorry Bryan marks), that's ridiculous. If you want your monster heel to job, it'll have to be in a believable manner or else it would hurt the gimmick.
To relive past eliminations, you can have your silly RKO out of nowhere, then he bounces up and takes a Chokeslam before Jericho lifts up his legs and makes him tap to the Walls... or you can have him run through Kane, Swagger, and Orton before he fights with Jericho for 10 minutes or so, and Jericho gets the pin in a way that looks like he's outsmarting Henry. That could work. Would WWE do it? Who knows.
Assuming he's winning here (lets face it there's really nothing else for him to do at 'Mania), and he jobs to Alberto, you know Henry will take Alberto out setting up Dolph. That's fine.