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I don't see it happening. There are a few reasons why:
1: Having someone break the streak really seems like a silly thing. Because it is taken for granted that Taker will win, having him lose would be unlikely to create the greatest mark out moment, and more likely to create a 'wtf' moment. And not in a particularly good way. Granted a scenario could be built in which Taker losing would be a genuine mark out moment - say him facing a younger star, who has his own streak going (and not just a 1-0 streak). That would require a few years of getting someone built up to it - and with Taker I doubt there's enough years left.
2: Having HHH win it would just be stupid. First off, he doesn't need it at all. Not only is he over decently, he is as close to in bed with his boss as he can get. There's just no reason for giving it up to HHH.
3: It would leave a gap for next Mania - where Taker will prolly still fight - that couldn't be filled with "Will the Undertaker remain (almost) undefeated at Wrestlemania - or can John Cena break the Deadmans streak?". There's not really much prestige in defeating Taker 2. at Mania - it would make Cena the Buzz Aldrin of the WWE. (And I'm not saying that Cena is gonna defeat Taker next year. He's not... well prolly not...)
Summing up the above: No - HHH wont win.
To answer the question actually asked by the OP:
I would initially be like - WTF! *facepalm* - then I would go here and read post after post about how HHH is a self-serving asshole and how Taker was prolly threatened into giving his streak up for HHH.
After that I would just continue to think that it was a stupid move.
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