I think Punk winning is a given. Whether it makes Llesnar look weak or not, the fact is Lesnar is an attraction while Punk is there for the long haul. Punk is more valuable to the company and will be there for many years after Lesnar has gone again. So Punk will definitely go over I think.

Thanks Taker_2004 for the banner!
Punk apparently has just about 1 year left on his contract which brings about some interesting thoughts on how Punk will be booked over the next year, as they surely cant afford to let his contract run down as low as it did last time, but will Punk want to re-sign? as he always said he didn't want to do this forever and after enjoying a 2 month break, will he want to walk away? Either way, how could this effect how he is booked?
As for Lesner so far he has Lost at Extreme Rules to Cena, Won at Summerslam against Trips, Lost at WM against trips and Won at Extreme Rules against Trips so if they are going to reverse perhaps the order this year with him winning at Extreme Rules this year, he would Lose at Summerslam and then Win at Wrestlemania? Just a thought...

Either way one guy is most likely going to suffer damage because of the shitty WWE creative team. I just hate it that it's going to be one of my all time favs either way you go.
I think Punk winning is a given. Whether it makes Llesnar look weak or not, the fact is Lesnar is an attraction while Punk is there for the long haul. Punk is more valuable to the company and will be there for many years after Lesnar has gone again. So Punk will definitely go over I think.
He will, unfortunately Lesnar will really, really hurt him. So he'll have to recoup for a while.
Lesnar will win the first one, then Punk gets the return match. Same as Triple H

Paul Heyman is sounding a little gay tonight.
This is the feud that most of us have been waiting for since Lesnar's return to WWE. The only thing I worry is that they have done such a shitty job of booking Lesnar since his return that it's going to be rough going forward in this feud. He is 2-2 in his matches since he's been back. He looked great against Cena in a loss which should have been a win. Then he was made to look like he was an equal to HHH which again was a mistake. Even in the two wins he had in that series of matches, he didn't look like the destroyer he should be. He was made to be a weak heel relying on Heyman's distractions and cheating to win matches. Now he is going against Punk who is the #2 guy in the company and how are they going to make this work? Punk can't afford to lose right now. He just returned to action after losing his last 3 ppv matches in a row plus that epic #1 contenders match with Cena. Granted he won at Payback but that makes him 1-4 his his last 5 big matches. Having him lose now would kill his momentum. The aforementioned issues with Lesnar's booking. If he loses again how can they make him the big time attraction he should be if all he does is lose? If Lesnar wins, it should be clean but that would hurt Punk too much and if Punk wins, it has to be clean to continue his babyface run. Punk is drastically smaller physically than Lesnar so he can't beat him with brute power moves like HHH and Cena were able to do. He could be a punching bag and pull off the out of nowhere win but again that hurts Lesnar to much. I am very interested to see how this plays out because of WWE's history of screwing up big time feuds. I want to see both men booked appropriately but this is going to go badly for one of them. I just don't know which one. My money is on Lesnar losing.