10 WWE Stars Who Would Have Won Money In The Bank In The 1990s

9. 1991 - Jake 'The Snake' Roberts

Owen Hart Money In The Bank
WWE.com

How beautiful would this have been? Jake Roberts turned heel in the summer of 1991 after betraying The Ultimate Warrior. He would then go on to have an absolute all-time classic feud with 'Macho Man' Randy Savage, a story that is one of the first I truly remember as a fan. Heel Roberts stands tall as one of the greatest wrestling characters ever.

But let's say the match happens before the turn, and Jake Roberts wins the briefcase as a babyface. The crowd would have loved this, as Jake was immensely popular at the time. It would have been a sign that their hero was finally getting his chance, only for horror to take over as he turned evil and became a dastardly villain with power in his hands.

With the World Championship vacated towards the end of the year, a Jake Roberts lurking in the background with a briefcase and a King Cobra would have made for some incredible wrestling television. The line-up for the match would have been pretty stacked too, with 'Rowdy' Roddy Piper, Bret Hart, Ricky Steamboat, Davey Boy Smith, Haku and Rick Martel (of course) in there as well.

Contributor
Contributor

Born in the middle of Wales in the middle of the 1980's, John can't quite remember when he started watching wrestling but he has a terrible feeling that Dino Bravo was involved. Now living in Prague, John spends most of his time trying to work out how Tomohiro Ishii still stands upright. His favourite wrestler of all time is Dean Malenko, but really it is Repo Man. He is the author of 'An Illustrated History of Slavic Misery', the best book about the Slavic people that you haven't yet read. You can get that and others from www.poshlostbooks.com.