The 'McMahon's Million Dollar Mania' segment, which aired for a few weeks on Raw in June 2008, saw the WWE Chairman give fans a portion of $1million of his own money during the show.
The concept was simple, fans would register to enter a prize draw, and would have to watch Raw for the chance to win a portion of McMahon's $1million.
McMahon would call selected fans during the show, where they'd have to give a special password to win the money. However, things didn't always go to plan.
As you can expect from a 62-year-old trying to operate technology on live TV, Vince McMahon occasionally dialled the wrong number, which admittedly did make for some pretty funny moments.
One viewer even walked away from $50,000 deciding to leave McMahon an unforgiving voicemail live on Raw.
However, some fans did legitimately win a portion of McMahon's money, using it to take their family on vacations or attend WrestleMania shows.
The segment was an attempt from WWE, after growing pressure from the USA Network, to increase the ratings for Monday Night Raw.
This rather innovative idea wasn't successful, however, with McMahon not only losing out on money, but also losing viewers for his flagship show by the week.
McMahon's Million Dollar Mania only lasted a few weeks, with the set eventually collapsing on the WWE Chairman after just three weeks to officially write him and the segment off TV.
Vince McMahon has been in the news lately, reportedly being angry at Charlotte Flair for walking away from him after she had a heated exchange with Becky Lynch.
You can read more about what went down between Charlotte Flair, Becky Lynch, Vince McMahon and Sonya Deville backstage at SmackDown by clicking here.News Now - Sport News