Here is how I would have the Rumble go (Obviously it's too late for this plan, however):
Ric Flair forces Jericho to defend his title in the Rumble, sending him in at #1, so you get
#1: Jericho #2: Triple H
Both ment last the whole time, but while Triple H is kicking ass and sending people out, Jericho is hiding in the corner, only sending people out when he sees an opportunity to sneak up from behind and get back to the corner safely. Eventually, it comes down to Jericho/Triple H as the last two, after Triple H throws somebody out. Jericho then sneaks up from behind and clips Triple H's knee, working it over before Triple H makes a comeback and almost knocks Jericho out before his knee gives out and Jericho tosses him to retain. Triple H would then go on to beat Jericho for the title at Wrestlemania.
However, since that can't happen, I say Triple H wins it.
"This team is in the playoffs and we expect to do some damage because every team up there, we can play with." -- DT Warren Sapp
This is without a doubt the best question in the history of questions. But also the most difficult. I think scholars would met there match trying to figure this question out. Trish loses some points for her love of hip-hop (not my thing)