This is where it clashes, as you mentioned, Phil has won those contests, but not due to corrupt politics. He won because he possessed the superior physique, apparently, judging by the pictures.
In your hypothetical example, Brandon Curry wins the O no matter how he looks. There's a "little" difference there.
The judges can not possibly appoint him Mr. Olympia no matter how he looks because he has not previously placed high in the contest, differing from Jay Cutler.