#1 - Hell in a Cell vs. Braun Strowman
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In my opinion, Braun Strowman would be the perfect person to retire The Undertaker, especially in a match like Hell in a Cell. Also, I'd book this to be a complete one-sided squash in favour of Strowman.
The idea here is that you do one of the most brutal Hell in a Cell matches in recent memory, and after a dominant win by Strowman, WWE can send The Undertaker off the right way, as he'd be putting over probably the biggest potential star the company has on his way out.
Having Strowman retire The Undertaker might guarantee that he's a heel forever unless you have "The Deadman" come back at some point to endorse him. But, even that probably wouldn't be enough.
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Edited by Rohit Nath