It's more that he doesn't mind temporarily losing if it works in the long run. He's the guy I originally thought would be a funny "Wrestlemania Undertaker" opponent because he absolutely would realize that deliberately losing in a Montreal Screwjob-esque finish would do way more to taint the streak and hurt 'Takers fans than actually winning would, and would endeavor to make it happen. And also that he doesn't get personally involved until the end of each story arc, which is also the part where things can never be 100% rigged in his favour.
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We clasped our hands, our hands in praise of a conquerors right to tyranny