1994
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Who won: Bret Hart and Lex Luger
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Who should have won: Bret Hart alone
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1994's Royal Rumble was a strange case, but Bret Hart should have won alone. The Lex Luger ship had sailed by that point and he would soon find himself back in WCW to usher in the era of the Monday Night Wars.
Meanwhile, since Bret Hart was destined to walk out of Madison Square Garden with the title anyway, the whole coin toss situation was more confusing than helpful, even if it added to the obstacles that Bret would need to overcome.
Edited by anirudh.b