Triple H has done it all in the world of sports-entertainment…well, almost. The Game has held just about every championship there is to hold and is even a 10-time World Champion. He has defeated all of the top names of his generation including The Rock, Kurt Angle, Stone Cold Steve Austin and Undertaker just to name a few. But there is one thing that Triple H hasn’t done in his illustrious career – join the Mr. McMahon Kiss My Ass Club. That can all change Monday night when the King of Kings has the opportunity to join the exclusive club in Pittsburgh.

For the last few weeks, Triple H and the Chairman, Mr. McMahon, have had a series of misunderstandings. Three weeks ago, Triple H was supposed to level Shawn Michaels with a sledgehammer. However, HBK moved at the last second, and The Game knocked out Mr. McMahon’s son, Shane, instead. Then, two weeks ago, Triple H was supposed to make up for the miscue by doing the deed once again. After the Spirit Squad had beaten HBK senseless, the Cerebral Assassin looked primed to seal the deal. But he apparently was taking too much time for the eager Kenny. The Spirit Squad member grabbed the hammer himself, sending Triple H into a violent fit of rage. Instead of leveling HBK, Triple H took out the entire Squad. Then last week on RAW, Triple H faced Kenny in a Spirit Jack Match. The Game somehow overcame the entire Squad again, prompting Mr. McMahon to give Triple H the most difficult challenge of all – joining the Kiss My Ass Club.

It is a very exclusive club, and it’s actually ironic that the most recent member of the club is Shawn Michaels. If HBK hadn’t moved at the last second three weeks ago, Triple H may not have even been in this position.

On February 27, it was HBK’s former tag team partner Marty Jannetty that was supposed to join the club. But Jannetty refused, and instead took the Master Lock Challenge. It was all a setup and he was attacked by the Masterpiece. The Showstopper came to his rescue, but he was ambushed by McMahon and his son Shane. After incapacitating HBK, Shane pushed Michaels’ face into his father’s rear end and made him pucker up.

Although HBK is out of action and was unavailable for comment on the experience of joining the club, WWE.com caught up with the other two members of the exclusive club – William Regal and Jim Ross.

Regal had sided with the Alliance, but once the Alliance was squashed in late 2001, he came crawling back for his job. The only way to do that was to join the Mr. McMahon Kiss My Ass Club.

“I was the first member of the club, and I’m proud of it as well,” said Regal. “Sometimes a man has got to do what a man has got to do. I needed to do that to get my job back and keep myself in WWE, so I have no qualms doing it whatsoever.”

RAW play by play man Jim Ross has a different take on the experience of literally kissing his boss’ ass. Just a couple of weeks after Regal joined the club, Mr. McMahon thought Stone Cold would be joining. Instead, Stone Cold low-blowed the Chairman, which prompted J.R. to begin laughing. Mr. McMahon spotted J.R. and took it as a sign of disrespect and ordered that instead of Stone Cold, it would be J.R. joining the club. The voice of RAW, against his own will, was forced to pucker up and be humiliated in front of his friends and family, as RAW was in Oklahoma, his home state.

“It was probably the most humiliating night that I’ve had in my thirty plus years in the business,” said J.R. “I’d rather just get the hell beaten out of me, and that has happened, but I’ve gotten over getting the hell beat out of me easier, from a mental standpoint, than having to live with the stigma that I kissed Mr. McMahon’s ass on national television. And not only did I do it on national TV, I did it in my hometown and in front of my family.”

While joining the club was one of the most humiliating moments in J.R.’s life, Regal feels differently about his experience.

“I woke up with a Brazilian transvestite in Hamburg once. That was far more embarrassing,” said Regal.

Regal may have J.R. beat with that one, but regardless, one has to wonder why Mr. McMahon even created such a club. J.R. certainly has some ideas on that as well.

“He is the most powerful man in sports-entertainment and has been for a long time – it’s not even like there is anybody who is a close second – but for some reason it seems like he has many insatiable desires. And apparently, one of his insatiable desires is to continually reestablish the fact that he is the man,” said J.R. “He signs our checks and he gives us our marching orders. He’s the General, and if you’re a soldier, you do what the General tells you as best you can or you get court-marshaled or put in front of the firing squad. This is almost like it’s something figurative, like Triple H is being put in front of the firing squad.”

The big question heading into Monday night, is will Triple H really join Mr. McMahon’s Kiss My Ass Club, or can The Game find a way to escape the “firing squad”?

“All I can say for Triple H is that I gave him the nickname years ago of the Cerebral Assassin. I always looked at him as a thinking man’s wrestler. He’s a real manipulator, he’s beaten everybody there is to beat, but this is going to be a hard charge to beat because I don’t know where the middle ground lies. What do you do, negotiate the left cheek vs. the right cheek?” said J.R. “Triple H may be known as a 10-time World Champion, and he’ll probably be in the Hall of Fame some day, but he’ll be going into the Hall of Fame with one thing on his clip reel and that’s him kissing Mr. McMahon’s ass at the Civic Arena in Pittsburgh. I found it ironic because possibly the most proud WWE Champion still resides in Pittsburgh – Bruno Sammartino. And I consider Triple H to be like a modern-day Sammartino. It would be like saying ‘Bruno, you’re coming to RAW in Pittsburgh and you’re getting on your knees and you’re kissing my ass and there’s nothing you can do about.’ That’s essentially what he’s told Triple H.”

Will Mr. McMahon be able to put Triple H through the most humiliating moment of his career? Or will the Cerebral Assassin be able to somehow manage his way out of another Mr. McMahon challenge just like he did in last week’s Spirit Jack Match? Tune in to RAW at 9/8 CT on the USA Network to find out.