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I love that MITB has been "money" so far, with an 8/8 ratio. But I think someone should eventually lose.
I'm not sure if that will make that person look awful, but you have to plant the seed for some doubt. Otherwise it's as if the wrestler is just winning the world title when they win the case initially.
Although I suppose the longer the streak of successful cash-ins goes on, the more doubt may be involved with each.
They probably don't even put this much thought into it. The plan is probably just to have everyone who wins the case succeed until the gimmick is no longer viable.
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