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They had plenty of chances to do it, but they chose not to.

Instead of Undertaker vs Triple HGH 3, they could have gone with Undertaker vs Cena. Instead of Undertaker vs Wyatt and Triple HGH vs Sting, they could have gone with Undertaker vs Sting.
I think they could have replaced Cena with one of the HHH matches at the very least and I actually thought they were saving UT/Cena for WM 30.

UT vs Wyatt was also a time they could have done Cena, but imo Cena vs streak was the best drawing card.
 

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When would have been the best time to do Cena/Taker at WM in your opinion? Or is this a match that was right not to happen?
When.. probably 2009-10 was best time. Obviously you don't do Shawn vs Taker then but Shawn and Taker 2 didn't do anywhere near as well at box office as was expected.

Taz beat a Kurt Angle who hadn't been given a push yet - well after that, Angle had beaten Rock, Austin, HHH, Kane, Triple H, Hogan, Lesnar, Big Show, HBK etc so that's a strange choice. Cena beat the guy (twice I believe) who beat all of those guys.

By Mania 23 Cena had beaten everyone he had ever faced the previous 3 years.

Beating Angle wasn't some great accomplishment though. Styles has beaten Cena and Orton but doesn't mean he that beating Styles means you are suddenly super strong.

All guys getting rising push in WWE circa 2000-06 beat Angle. Benoit, Guerrero, Brock, Mysterio
 
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