1997
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Who won: Stone Cold Steve Austin
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Who should have won: The Undertaker
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Winning by trickery, Stone Cold's victory was overturned and didn't add anything of consequence to the WrestleMania title picture, although Shawn Michaels' infamous "lost my smile" promo also blew up the plans that year. Additionally, Stone Cold was hot, but he wasn't yet the man who would define the Attitude Era. That would have to wait another year.
The whole thing was a big mess, so it's hard to say who should and shouldn't have won, but Undertaker seems like the best choice in hindsight, given what happened.
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Edited by anirudh.b