If Helmsley does show up in the Rumble, where is the proper place for his appearance. One seems to early, forty seems to late. I imagine they give him an early 30's slot when the last of the main eventers usually show up, but wouldn't bringing him in around 5-7 be a big way to jump start the Rumble, get fans juiced, allow him to throw out a bunch of guys while not having to win the whole thing because of the number drawn?
for the record, his last loss was April 21 against the Undertaker. That was the #1 contender match, I believe. His last singles loss before that was February 17 at the PPV when Jericho beat him to retain his undisputed title.