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This is effectively a lose-lose situation.
If Drew loses, he becomes effectively buried and would basically NEED to fuck off for like half a year so people can want him back, otherwise he'll be a heel jobber that people will start shoot clowning on.
If he wins, it'll be extremely predictable, because losing is such a negative option in this scenario and no one would be reasonably excited for it.
The worst part of this is that it seems to be a retelling of the AustinH feud where H tries to get Austin to swing at him due to a contract, except done much worse. There's a lot of other reasons why this angle is stupid and bad writing but that'd be a lot of words.