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Kenny came first in a period where business was on the way up and got to work people you've actually heard of and other great workers in their prime. He was the tourist's first experience to the modern heavyweight wrestler.
Ospreay came when business was going down and stars were aging out or leaving for other promotions while outside fan interest was cratering. All he had were Meltzer stars. It doesn't matter if you think he can do more impressive shit than Kenny, Kenny came first and that's all that matters.