#3 Former WWE World Heavyweight Champion Christian

Former WWE Superstar Christian is tied for the second most Money in the Bank ladder match appearances in WWE history.
The current AEW wrestler appeared in the very first Money in the Bank ladder match at WrestleMania 21 in 2005. That match was ultimately won by Edge but marked the first of six Money in Bank ladder match appearances by Christian in the following years.
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Christian competed in the final two Money in the Bank ladder matches to be held at WrestleMania events. This was in 2009 at WrestleMania XXV and 2010 at WrestleMania XXVI. Those matches were won by CM Punk and Jack Swagger respectively, both of whom are also no longer under contract with WWE.
Christian then competed in the World Heavyweight Championship contract Money in the Bank ladder matches at the 2010 and 2012 WWE Money in the Bank pay-per-views. Unfortunately for Christian, the ladder matches were won by Kane and Dolph Ziggler respectively.
Captain Charisma competed in his final Money in the Bank ladder match at the 2013 Money in the Bank pay-per-view. Christian challenged for the WWE Championship contract, but the Money in the Bank briefcase was ultimately retrieved by Randy Orton.
After suffering a serious concussion on Monday Night RAW in March 2014, it was later announced in the year that Christian had quietly retired from in-ring competition.
After making sporadic appearances on WWE programming over the years, Christian finally returned to in-ring action earlier this year as a surprise entrant in the men's Royal Rumble match.
However, it was subsequently revealed that Christian was not under contract with WWE and was a free agent. In a shocking move, Christian signed with All Elite Wrestling, making his debut on the AEW Revolution pay-per-view in March 2021.