He has very few matches throughout the year. Wouldn't they be best spent in big name matches?
Depends on how you look at it. Big name matches are likely to be bigger draws, I'll grant you. But I think in the long run, they'd be better off using Undertaker's few remaining matches to establish new stars. Think about the future. Who on the current roster do you see carrying the company in, say, five years? Pretend Triple H is gone, Cena is gone, HBK is gone, Undertaker is gone... who's the star? Who's the next big thing? Whoever your answer is, why not put THEM in a match against the Undertaker at WrestleMania? Let him help springboard them into superstardom.
Swagger? No, you're right, he probably wouldn't work at all. I don't even know why I mentioned him. But what about Ziggler? Personally, I think he could be an ideal choice. His offensive style isn't that high-impact, so they could have a prolonged match without Taker having to risk getting hurt by taking a bunch of major bumps. Meanwhile, Ziggler is outstanding at selling other people's moves; I'm confident he could help make Taker's arsenal look absolutely devastating. Taker would get to brutalize Ziggler, thus reasserting himself as a destructive force of nature, and Ziggler would get the opportunity to show off his skills and prove that he could hold his own against someone like the Undertaker. I honestly think they could have a classic match together, and it would go a long way toward giving Ziggler some credibility as a star. Everybody wins.
(By the way, please forgive me for my ramblings in this thread. I don't get to talk about wrestling very often. When I do, I sometimes go overboard. Sorry bout that. If you guys want me to shut up, just say so.
)