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Now I don't know the guy, but just from what I've read/heard Undertaker wanted the streak broken. He's got an old-school mentality and wants to put someone over on the way out. That's great, but him putting over Lesnar hasn't really done much long-term now, has it? (granted the plan was for Lesnar to break the Streak, destroy Bryan, then fall to Reigns... lol) but if Taker would put over KO on the way out the door, that would do so much for him, right?
I'm not as bothered by Strowman as most, he can stick in his current role as long as he wants. That's great. He adds variety. But it's not like he's gonna main event
Yeah, Taker offered the Streak to a few people before Brock was chosen to end it (Kane, Orton, Angle, Batista I think as well...), so I don't think he has any particular problem putting someone over at WM. It's really Vince's call.
Problem is, it's safe to assume that Taker will probably never lose at WM again until the year he retires, and despite many people assuming that he will this year, there's been no strong rumors or conformation of that being the case. So I fully expect him to win regardless of whom he faces. (He would have put over Lesnar had they waited till WM to do Brock/Taker III, but that's just putting over the guy you already lost to, which is different. Then again, maybe the reason they blew the feud off at HIAC was because Taker was thinking about hanging it up at 32 and was gonna let his greatest nemesis Brock lesnar be the man to do it, but then he changed his mind. I seriously doubt they'll let an entirely different superstar go over him until he's absolutely sure he's reached the end of his career, though.)
As far as Strowman goes, I don't mind him per se, since he makes a unique addition to the Wyatt Family, but being the colossus of the group is really the only reason I care about him. Off on his own with the same strong booking, I probably wouldn't give a shit about him at all. Him vs Taker still sounds awful.