1) Would you have Chris Jericho beat Dolph Ziggler for the MITB Briefcase?
Not at all because Ziggler is the one that needs his career elevated to the next level, not Jericho. Jericho's great, one of the overall best in the world today in my opinion, but Ziggler needs to come out ahead over Jericho. For all intents and purposes, the peak of Jericho's career as it pertains to titles & main event status is pretty much over with. He's stated himself in interviews that his music is his #1 priority professionally at this point in time. The only reason he's returned to WWE over the past few years is because he's having fun and is being allowed to work with guys he truly wants to work with, such as Punk & Ziggler, because he's stated multiple times that he's a big fan of their work. Jericho has won multiple World Championships, he's held the IC title more than anybody, he's won the tag titles on a numer of occassions and he's still among the overall best pro wrestlers in the world. Jericho is someone who is probably Hall of Fame bound within the next few years.
2) (If he did win it as they seem to be heading that way) Would you have him win or lose when he cashes it in?
They seem to be heading towards having Ziggler drop the case to Jericho? What do you base that on? Thus far, the only interaction they've had is Jericho hitting Ziggler with a cheap shot, namely hitting him with the Codebreaker, and Ziggler returning the favor by giving Jericho a cheap shot & setting him up to eat a Brogue Kick from Sheamus on last night's Raw. Given that Jericho could well be gone at just about anytime to continue his work with Fozzy, the odds of him taking the briefcase are slim to none. However, if he did win it, I think it'd probably be best if he did cash in but fail to win the WHC. As I said earlier, Jericho is back mostly because he's having fun and being given a chance to work with guys he really likes. He's not there to win titles right now.
3) Finally considering he has put over EVERYONE since he returned and hasn't won at a PPV in something like two years, Do you think Chris Jericho will ever be effective as main eventer again?
Jericho is someone that has partially made a career of putting just about everybody over yet still coming out shining like a brand new penny. At the end of the day, Jericho's best trait is his ability to come out on the losing end of most of his feuds while keeping his stock surpremely high. Why? Because he's just that fucking good. Whether it's cutting promos or wrestling inside the ring, Chris Jericho has been one of THE top guys in all of wrestling for more than a decade. His work is consistently high quality and fans have noticed that. I'm not just saying that because I'm a fan of Jericho's, it's just how it is. Whether it be Mysterio, Orton, Cena, Sheamus, HBK, Triple H, The Rock, Stone Cold, Taker, CM Punk or any other huge name that Jericho has ultimately gotten the worst of when it comes to a feud; Jericho always comes out smelling like a rose. In order for Jericho's effectiveness as a main eventer hasn't been depreciated by this quality. In my view, it's something that's helped to cement his status. Jericho is someone that can be counted on as a go to guy when you want a veteran to help put over a young star while still looking like a world class wrestler all at the same time. Very, very few people are able or would be able to succeed in this same little niche that Jericho has.