#1 - Kane (7)
The surprising leader on this list is none other than the Big Red Machine, Kane. When you think about Money in the Bank ladder match veterans, you would think of the previous names like Jericho, Kofi and Ziggler. You wouldn't think of Kane. However, Kane has taken part in seven MITB ladder matches in the past.
He did not have many impressive individual spots but was always an intimidating figure in his matches. He was part of the first one at WrestleMania 21 when all the ladders caught fire during his entrance in a spectacular scene. Since then, he's competed at the last two Money in the Bank ladder matches at WrestleMania, the Smackdown briefcase match in 2010 and 2011, and the Raw briefcase match in 2012.
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His last Money in the Bank appearance was in 2015 as Corporate Kane, but he had parts to play in other years as well. He was scheduled to be part of the Raw briefcase match in 2013 before he was removed, following an attack from a debuting Wyatt Family. Kane also appeared in the 2014 ladder match to help Seth Rollins win the briefcase.
Kane was the first person to win the briefcase and cash it in on the same night. This happened at the first ever Money in the Bank pay-per-view in 2010. He does have a pretty prominent legacy in Money in the Bank history, more than we thought.