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I'd really have to nominate Christian. He was in the TIT Invitational Finals Ladder Match, The Triangle Ladder Match, TLC 1, TLC 2, TLC 3, TLC 4 whilst also having some pretty cool Ladder Matches with Edge, Chris Jericho and Rob Van Dam (I believe). He also put over Kaz in a recent Ladder Match, and he was in a Money in the Bank or two, and probably a King of the Mountain Match, as well.
Shawn Michaels is an innovator of the match, but really, how many great ladder matches has he been a part of? There were his two against Razor Ramon, and I think he jobbed to Triple H in a 3 Stages of Hell Match, with the last stipulation involving a ladder. He also had the first ladder match against Bret Hart.
Jeff Hardy is another guy, but he mainly falls off the ladders, and doesn't really win enough to be granted that title. I mean, he has been winning a few recent ones for the IC Title, but still. The guy also had most of his ladder matches planned by his brother, and the guys he was working with.
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