#13 Randy Orton
The Viper, Randy Orton won his first ever Money in the Bank contract in the year 2013 after he beat CM Punk, Christian, Sheamus, Daniel Bryan and Rob Van Dam in a bout which lasted nearly half an hour. Orton held the contract for 35 days before he cashed it in at SummerSlam 2013 and became the world champion.
Also Read: Ranking every MITB briefcase cash-in ahead of the MITB PPV
The Legend Killer has never been able to win a single Money in the Bank ladder match after 2013 despite being amongst the premier superstars of the company.
Randy is currently a part of SmackDown Live and he is set to represent his brand at the upcoming men's Money in the Bank ladder match. The chances that we may see the Apex Predator emerge as Mr. Money in the Bank of 2019 are very few yet nothing can be ruled out in WWE.