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I love that picture.
Anyway, what are the odds of Triple H actually retiring after losing to Brock Lesnar? Given how predictable the outcome of the three top matches are (Cena finally defeating The Rock and winning the WWE Title again in the process, Triple H getting his revenge over Lesnar, Undertaker going to 21-0 and reclaiming the urn), something tells me there is a twist in there somewhere. Like one of those three matches will have a different outcome than what we expect.
And of the three, it seems Lesnar defeating HHH and sending him packing is more plausible than the other two alternatives. If Cena lost, he'd just win the following month and from a story POV, him picking up the win at Wrestlemania is best anyway. CM Punk breaking the streak just right before taking time off isn't happening, and it'd be underwhelming for this storyline to be the build to Taker's legendary streak ending, and just plain dumb for the streak not to be apart of the big 30th Wrestlemania show. That leaves Lesnar winning and Triple H calling it a career.
Many find it hard to believe that Triple H would let a monster heel like Lesnar - who broke his arm twice, broke his best friend's arm and attacked his father-in-law and put him in the hospital - be the one to retire him. After all, his best friends Shawn Michaels and Ric Flair both retired at Wrestlemania against guys they respected and that the fans loved. Would Triple H really do the opposite?
In my opinion, it's plausible that he would. The reason is because they can easily play it up in a "you won the battle, but I won the war." sort of way. If Brock won but walked out barely standing, that would show that it was no easy feat for Lesnar to defeat HHH, and HHH could say he left the monster barely standing afterwards. Yeah, he won, but it's still not a victory he can gloat about. Another possibility is Lesnar trying to inflict further damage after the match but Triple H destroying him in the process and leaving him laying, despite him just getting the official victory minutes before. Another idea is Triple H giving a retirement speech the next night and being welcomed with a "Thank You, Hunter" ovation from the crowd, only for Lesnar to interrupt and cause another fight to break out, with Lesnar being laid out. Same as the second idea, only it happens the next night instead.
This way, HHH loses but still gets his 'revenge' in a way and goes out looking like a champ. Meanwhile, Lesnar wins and gets to walk on still undefeated (minus the Cena victory) and HHH is still gonna pop up time from time in his COO character and play a role here and there when its appropriate. And when it comes down to it, we all know complete 100% retirement is usually rare in wrestling unless there's a doctor telling you you could cripple yourself if you step in the ring just one more time. So there's always that chance HHH could step back in the ring a time or two more down the road, even though being the wrestling traditionalist he is, I would think he would want to honor the retirement by sticking to it and never wrestling again, just like his friend Michaels.