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Probably a combination of him playing backstage poltics very well, his youth since Vince just lost out on most of his older veterans (ex. Hogan, Macho, etc), and at the time he was a good counter to Bret Hart's style.
WWF could use Bret Hart to pull off great technical and athletic matches while also using HBK for great showboating and crowd reaction matches. Once they started feuding, WWF ended up having their top 2 wrestlers who could attract 2 different types of crowd along with the slow developing Canada-USA wrestling rivarly.
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