#1 He was managed by Brock Lesnar's wife
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Upon debuting in 1995, the rich snobbish Helmsley would be accompanied by a different woman each week, showcasing his wealth.
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For WrestleMania 12, he went the extra mile, introducing the fans to a new sensation: Sable.
Whilst Helmsley would quickly ditch the future Playboy star, he was instrumental in giving her her big start in mainstream media.
Sable would later marry former Universal Champion Brock Lesnar in 2006.
Edited by Kishan Prasad