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#5 Princess Kimber Lee - Chikara Grand Champion
Our next entry on the list comes to us courtesy of the wild, insane, and downright goofy CHIKARA promotion.
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Ostensibly a Lucha Libre styled wrestling company, Chikara has an 'anything goes' style of booking and character creation. One of their top stables are all wrestling ants. Yes, wrestling ants.
As a Lucha Libre promotion, albeit an insanely silly one, Chikara execs have never had any qualms about featuring intergender matches, and do so regularly. Kimber Lee led a team of underdog wrestlers (two of whom had ice cream cone gimmicks. No, they didn't eat ice cream; they WERE ice cream) to victory and won the right to challenge for ANY belt, at any time, much like cashing in the Money in the Bank briefcase in WWE except that it was for any title.
Kimber Lee waited until Grand Champion Hallowicked had successfully defended his title in a grueling match before cashing in. She locked in an armbar submission and won the Chikara Grand Championship in 2015.
Kimber Lee would become the first woman to hold ANY promotion's 'big belt,' beating larger companies to the punch.
