Dude, it makes sense. It's Flair country. Flair challenging for the World Title and overcoming the odds of Orton's a good main event. Some people on here read too much into everything.
Maybe they could have Orton and Flair discussing being on Flair country, and Flair thinking he should challenge HHH, and Orton doesn't know whos side to take, so he joins in the match, but leaves it to Flair and HHH, and in the end makes his choice by helping HHH win as he's the leader.