Originally Posted by The Sandrone
Like E_REA_AE, I think Taker could go to WM35 if he keeps up the pace of competing only once a year (at Wrestlemania). He seemed to be in pretty decent shape at WM28 after a year off, and if he keeps doing that his condition can only get better to the point maybe he could have one more year long run between WM34 and WM35 (or at least appear and compete throughout the year occasionally and have one very good feud outside of Mania).
Then again, he will be fifty-something by then, so it'd probably be better if he ends it at WM30, and honestly I think that's what's going to end up happening. If so his next two Mania matches should be Lesnar this year and Cena WM30. But if somehow he could make it past that, I think I could put something together going into WM33 (where he goes 25-0 to end it all):
WM29- vs. Cena (21-0)
WM30- vs. Rock (22-0)
WM31- vs. Orton (23-0)
WM32- vs. Lesnar (24-0)
WM33- vs. Ryback (25-0)
My reasoning for this? WM29 he faces Cena and Rock faces Lesnar. Taker wins. Rock wins. Taker/Rock happens WM30. Then after that Orton can be built up as a dangerous heel with new life, and they could build up the punt kick again as the be all end all, which would create a great moment in the match when Orton manages to hit it. Plus it's 10 years after their first Mania match, which is something else that also brought it mind. WM32 if Lesnar is still willing to compete, you put him against Taker. You could also swap Lesnar and Orton to keep Taker's opponents building from Cena to Rock to Lesnar (granted in star power Lesnar is a step down from Rock, and if Rock beat him at WM29 that would work against that as well, but let's work with it). Finally WM35, he faces Ryback, who if he ends up truly being the Goldberg of this gen, it would be a huge match, especially since we never did get Taker/Goldberg. Obviously it's hard to imagine right now since Ryback is new, but this is 4 and a half years from now, and hell, Cena, and Rock were the respective top guys of their generations within 3 years, so who knows. I don't even need to get started on Lesnar to prove my point. Ryback's definitely not my favorite, but there is something about him that I think could be huge. Maybe it's the Batista/Goldberg mixture vibe I get from him that makes it seem like he could be the top star. While he may never reach where those two were, you never know. He already has the crowds in the palm of his hands with the whole "feed me more" shtick. But all in all, Taker/Ryback by that point would be a huge match, and potentially worthy of ending Taker's career on, while giving Ryback one last push up if he even needs it by that point.
I also understand people feel Taker's career should end on Kane, but tbh I'm not sure. Taker's legacy doesn't revolve around Kane, but if they wanted to end Kane's career at The Undertaker's hands, that would make more sense to me. Not that Taker's career ending with Kane doesn't make sense, but I think he's just become so much bigger to the point while that storyline back in 1997-1998 between the two may be the greatest storyline of all time, Taker's had bigger feuds that overshadow it on a starpower level. Plus they've feuded a billion times in the last 14 years, so honestly it's not something I'd be super excited to see personally.