8 Times Vince McMahon Regretted Huge WWE Contracts
1. Bret Hart
Arguably the most famous contract negotiations in the history of professional wrestling - largely because so much of it was showcased in the Wrestling with Shadows documentary - is the situation involving Bret Hart back in 1996.
At this point in time, Hart was the best wrestler on the planet - sorry Shawn fans - and was one of Vince McMahon's most loyal of soldiers. Whereas so many former WWF mainstays were now competing for Ted Turner's WCW, the Hitman was happy to stay with the World Wrestling Federation. So happy, October 21, 1996 saw Bret sign a mammoth 20-year deal to remain with the company.
With the green, green pastures of WCW waving ludicrous amounts of money at Hart, he instead opted to take the lesser amount of a reported $1 million a year to stay with the organisation for whom he'd worked since 1984. That salary would reduce once Hart's in-ring days were over, and Bret would then transition to becoming a backstage producer for the WWF.
Fast forward to mid-1997, and the WWF was well and truly getting its ass handed to them by an Eric Bischoff-driven WCW product. As such, times were hard for the company - to the extent that there was a genuine threat of WWF going out of business.
For McMahon, he saw Bret Hart's salary as a major headache, and thus encouraged the Excellence of Execution to open dialogue with WCW to see if their previous offer was on the table. Not only was that offer - a supposed $9 million over three years - still on the table, but Vince even helped Hart negotiate with WCW so that McMahon could get out of the 20-year deal he'd agreed with Bret.