I don't really disagree with you, Homeric (and it's been over five years!), but still, Shaw isn't as, shall we say, prone to illegality (or at least to skirting it) in his momentary lack of scruples as is the preternaturally unscrupulous Caswell. Caswell is just greedy for money and is perpetually a user. Shaw wants position but resorts to desperate if inexcusable tactics only when his chance suddenly arises. When it evaporates, he reverts to being dislikable, perhaps, but not a bad or crooked man.
I think the film makes clear that Shaw allows his relentless ambition to get the better of him and use almost any means possible to get the top job, including not only unscrupulous but mean-spirited methods. Yet he's clearly a man of talent who honestly believes he's doing what's best for the company. Caswell is more of a routine opportunist, an amoral wheeler-dealer interested only in profit; he seems to have no productive talents, only a talent for the fast buck, and may not be very good at that.
Put it this way: Shaw does behave abominably, but his behavior is temporary, born of his chance to seize the presidency. (Another example of this bad behavior is his attempt to rush the election before everyone has shown up, in order to insure his victory.) Once beaten he seems to go back to being a decent guy with a desire to make the company succeed (even if his views are wrong-headed). Caswell, on the other hand, is just innately a liar, a manipulator and a louse.
Anyway, we all wanted Walling to win because of our idealistic view that the best man should win. He stood for the best in his company and the people he's responsible for. And, of course, he won.
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