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I wouldn't ever bet on it happening, but Rock/Undertaker would be the perfect sendoff for Rock's in-ring career as there is already a well-laid backstory to it should it ever happen.
The Rock has defeated Hulk Hogan, Steve Austin and John Cena all at a Wrestlemania. That's the three biggest stars other than himself who he can lay claim to beating all on the grandest stage of all. Add to that the multiple championships that he's won, the Rumble victory, the other long list of people he's defeated, the fact that he even won the WWE Championship one last time (and did so by ending the longest reign of the past 25 years), etc. Rock could say that after all the wins and accomplishments, after all the accolades he's built up for himself over the years, he's ready to go out with a bang trying to score his biggest victory of all, and that's defeating the Undertaker and the streak. Rock says it's something no man has done in over twenty years, and with all due respect for Taker, if there's one man who can do it, it's The Rock. Only then will he truly be able to cement himself as the greatest of all time. (And he fails, of course, but the story and probably the match too (in terms of psychology) would still be great.) $$$$$$$$$$$$$$$$$
Oh that is so epic. I'm dying for this match now. I hadn't thought it through like that.