10 WWE Stars Who Would Have Won Money In The Bank In The 1990s
1. 1999 - Shane McMahon
As much as we may hate to admit it, the McMahon family were so ubiquitous on WWF TV by the end of the decade that there is every chance Shane McMahon would have won the Money in the Bank ladder match in 1999. Heck, Shane was already European Champion that year, and with the family going up against Stone Cold Steve Austin frequently with power at stake, Shane running around with the briefcase would be somewhat inevitable.
1999 saw the Corporation and the Ministry of Darkness join forces, so one would assume that to ensure a Shane victory the match would have been somewhat loaded with men from that faction. Along with Shane, The Big Boss Man, Faarooq and Bradshaw would have likely made the match to act as enforcers for Shane O-Mac, to neutralise the three men opposite.
The brief faction known as The Union may have provided two of the other competitors, in the shape of jilted Corporation members Test and Ken Shamrock. My guess is the final spot would have gone to Edge, who was still aligned with The Brood - who had just split from The Ministry - at the time.
Either way, Shane McMahon with a money-filled briefcase would have been a sure sight in 1999.