Appearing at the very last telecast of WCW Monday Nitro, where he announced the purchase of WCW. Whether you like him or not; after all he's gone through from 1995 to 2001, it was probably satisfying for him to have finally reached his goal.
Black Saturday in 1985 where Vince bought Georgia Championship Wrestling and it's time on WTBS was a disaster. The traditional Southern fans hated the WWE's product, and the fact that Vince only bothered to provide Clip Shows didn't help. However, his recovery qualifies as a real-life CMOA. Vince negotiated his way out of the contract and then sold the timeslot back to Jim Crockett Promotions for one million dollars, money which he used to fund Wrestlemania 1. So in summary, Vince stole a timeslot out from under his biggest rival, sold it back at a huge markup, and that aforementioned rival ending up essentially paying for a successful and profitable PPV that made Vince even more money.
The way he grew up in a trailer park with an abusive step-father. He also had dyslexia. Comparing what he's achieved with his background, he's nothing short of The Determinator personified.
Yeah, it did involve irreparably damaging the career of Bret Hart, but you almost have to admire the cojones it takes to take something that was nothing short of a disaster for the business (revealing that everything is rigged, and that you literally just screwed a company man on live television) and turn it into a massive, massive boon via the invention of the Mr. Mc Mahon-Stone Cold Steve Austin rivalry. Pragmatic Villainy at its finest.