I think Triple H vs. Punk could very well happen, if for no other reason than for lack of any strong, credible babyfaces with whom Punk can feud between Night of Champions time, when he's presumably done with Cena, and January. Unless of course they have Cena and Punk feud all the way to Hell in a Cell in climactic fashion, which... Could
happen. Perhaps it'll be Show/Cena/Punk at Summerslam, Punk retains, then it's Cena vs. Punk in Boston at NoC, Punk retains but Cena gets some moral victory afterward or whatever, feud heats up and it gets blown off at Hell in a Cell. If that is the plan, it would buy them plenty of time to build somebody else or turn somebody (like a Bryan or whoever) for Survivor Series/TLC time. Of course, having Punk work three PPVs in a row with Cena is perilous because as we all know by now, Cena cannot go more than two PPVs in a row without getting his win. Show could take teh fall at Summerslam, though, there could be some extremely shoddy finish at NoC to piss Cena/whatever fans he actually has in his hometown and then the capper would be Punk outsmarting and out-sadism-ing Cena inside the Cell (lol, I can't believe I'm even talking about Hell in a Cell this way... they probably should scrap the PPV after the End of an Era match at Wrestlemania, but on the contrary, they'll see that match as having boosted HIAC's prestige and importance as a gimmick match to perhaps even increase buys year vs. year for that PPV). That would put Punk over with an almost minimal amount of damage done to Cena, with only one "clean" loss to Punk at Hell in a Cell.
I think Trips/Punk II is much more realistic now that Punk's heel, though. On one hand Triple H might not return until RTWM time but I can see Vince become antsy when Monday Night Football season is at its peak in the middle of fall and wanting Trips to work wtih Punk for at least a solid month. But again, that is a bit off in the distance at this point in time. All I know is I'd certainly like to see Triple H/Punk again, with no more vague, ambiguous "I'm sort of a tweener face, but I'm a complete douchebag asshole, too"/"Well I'm going to outshoot you, you shooting shitter shooter"/"Oh yeah? Well, you and Vince only dig bodybuilders," crap. Just a hot, heavy babyface legend Triple H vs. dastardly heel WWE Champion CM Punk. It would be cool if Punk were so well-booked that his crimes against humanity in WWE draw Triple H back out early from rehabilitating his broken body following Summerslam, which is the perfect precondition to letting Punk go over Triple H at Survivor Series or wherever, maximizing heat on Punk and sympathy for the fallen legend he's tormenting.
I also love the idea of Punk and Brock both being "Paul Heyman guys," and clearly you do, too, haha. Once Brock exits after halfway crippling Triple H at Summerslam, Heyman can indeed form an alliance with Punk and right there you have a mighty catalyst to bring Triple H back into Punk's world. Excellent thinking, there, Starbuck
Argh, why do I build up my expectations through forays into wishful fantasy booking at times like these?