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In spite of their age I'm fairly certain two legends like Sting and Undertaker could find a way to put together something special in front of 80,000 people or however many people are crammed into WrestleMania in a given year nowadays.
That being said, it was always going to be hard to figure out from a booking perspective. When Taker had the Streak intact, losing it to Sting would have made zero sense but having Sting drop his first WWE match would have been a bit of a wet fart as well. Now that the streak is gone, I'm still not sure how you book it. You have the same issue of not wanting Sting to drop his first match but do you really have Taker lose a second time in a row?
If the match HAD to happen, I suppose you have Taker avenge his streak against someone this year (or sit out entirely) while Sting goes over HHH. And then they face off at WM 32 with the build being that it's each man's retirement match. But that build still seems flimsy and I don't think they'd want Taker sharing his retirement moment with another retiring legend.
At the end of the day I've accepted the match won't happen for a variety of reasons and I'm fine with it. I've always been a big Taker mark and a MASSIVE Sting mark (grew up with WCW) and that's why it was a dream match for me. But it's not like WWE is missing some massive opportunity by not doing it. In fact I'd say most of the younger audience wouldn't even "get" it. People unfamiliar with WCW think Sting was WCW's Undertaker. In terms of being the most prolific "lifer", then yes. But as a character he was completely different.
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