Okay so this is a touchy topic.
-First of all, Jimmy deserved to be expelled, just like the clique leaders who took part in the whole thing. After all, they were the one who got their fellow clique members to fight. Not to mention the prefects who did nothing to stop the fighting.
-Crabblesnitch couldn't have heard the whole monologue. And if he did, why doesn't he seem to mind the fact that Gary talks about how Jimmy's actions were the reason for his "reign"?
-How could he let an expelled student back solely because he pretty much beat up most of the students in his school? Not to mention giving the Headboy title to some student he's never even heard about before, after deciding that he's a genius just because he's shy. Or the fact that he re-enrolled some other student just because one of his worst students claims that she was unfairly expelled.
-And what about the fact that neither Jimmy or the Headmaster paid any mind to the fact that Gary could be dying on the ground next to them.
-Oh and the way the students, mostly clique leaders are cheering on the guy who beat them to the ground just minutes ago. And where the hell were the teachers/staff members who appear at the end?
The ending itself was disgustingly cheesy, but the Final Showdown mission was amazing.
The first time I played it, I was so sure that Jimmy was expelled for good. And the Final Showdown wasn't going to change anything. Gary's speech, as taunting as it was, had me in awe. If the game had ended realistically, Gary would've been right. No matter the outcome of their fight, he was still going to be on top, and Jimmy was still going to be expelled.
Regarding the fight itself, I don't think that it was meant to be hard, because of them^reasons, but also because:
1) Gary isn't some brute with gigantism and an impressive arsenal of wrestling moves.
2) He isn't a trained pugilist or one of the toughest kids from the wrong side of the tracks.
3) He didn't have a whole clique to back him up.
It was just a 1 on 1 in a small area. And probably the only boss battle that didn't actually change anything.
Gary had lost the moment they stepped outside on the roof and started his monologue.
P.S. I really can't figure out HOW he tied Crabblesnitch up, or if he was the one to do it at all, seeing as a few bullies were also in the building.