While it’s all a work, writing a great storyline and character to be some sort of diabolical mastermind helps to make some truly great heels in professional wrestling. Like every great evil overlord, when the heel starts making moves two to three steps ahead that makes for a real compelling story. When it happens quickly, their cunning leads to a big shocking moment.
No matter the era or the promotion, when you have dastardly heels with plotting minds that plot destruction, you get professional wrestling heels done the right way, instead of looking for cheap heat.
9 Seth Rollins
It’s not called “The Heist Of The Century” for no reason. Seth Rollins saw that he would be just another guy to Roman Reigns growing power and decided to swing a steel chair and The Big Dog and Dean Ambrose.
In less than a year, The Architect was the WWE Champion and did so in a huge way - the first ever WrestleMania MITB cash in and the first ever to happen during a match. Nowadays, his constant Joker style laughing is throwing opponents off their game all over the world.
8 The Miz
While The Miz does tell anyone who will listen that he is a two-time Grand Slam champion, he kind of achieved this achievement ever so quietly through calculated and cunning moves over the years. His first cash-in was against a defeated Randy Orton. His second came at the hands of first conniving his way into convincing Otis to put up his briefcase against The Miz in a match.
Phase two of that plan was working with Bobby Lashley to destroy Drew McIntyre, making him easy pickings for The A-Lister, in exchange for a title match. He unfortunately didn’t plan for how to dismantle The Almighty.
7 Edge
When you’re called The Ultimate Opportunist, you’re bound to have a few tricks up your sleeves. Edge was the first ever MITB briefcase holder and through his planning set the stage for how to cash in - as he picked the bones of a weary John Cena, who was the first one into the Elimination Chamber and survived the whole match.
Several years later, with Kennedy getting himself injured, Edge found a way to snag Kennedy’s briefcase and again cash in successfully.
6 Ted DiBiase
It wasn’t enough for Ted DiBiase to try and buy the WWE title from Hulk Hogan. After all, the pure of heart Hulkster had turned down the sizable offer from “The Multi-Million Dollar Man.” Instead, DiBiase concocted a huge scheme and had the money to finance it.
First, he procured the services of Andre The Giant. Then he paid copious amounts of money to some poor schmoe to get made up to look like referee Dave Hebner and be a very biased referee in the big Main Event WrestleMania 3 rematch almost worked had it not been for Jack Tunney stripping new champion Andre of the belt, thus nullifying The Giant giving the belt to The Million Dollar Man.
5 The Four Horsemen
As far as dirty deeds go, they don’t come cheap when it comes to Ric Flair and The Four Horsemen. The Horsemen were always one step ahead of their enemies like Dusty Rhodes to Sting, The Road Warriors and were able to turn babyfaces like Brian Pillman and Steve McMichael.
The group's constant calculated cunning is what made them the most respected faction in history.
4 Randy Orton
The diamond that Randy Orton has become in his career is something that every wrestler should aspire to. But he also is a cold and calculating, evil man when he wants to be. Besides assaulting and accosting any and all legends who stood in his path, Orton concocted several schemes in his career.
First, he plotted for over five years, waiting and biding his time to strike back against his former mentor Triple H. He targeted not just The Game, but the entire McMahon family, culminating at WrestleMania 25. While he was not successful there at winning the WWE title, The Viper did play mind games with Bray Wyatt on two separate occasions and was able to defeat The Fiend at both WrestleMania 33 and four years later at 37.
3 Eric Bischoff
Whether it’s in real life as a shrewd businessman or on-screen as the secret mastermind behind the nWo, Eric Bischoff knows a thing or two about being a criminal mastermind. He had secretly been running the nWo for months, including hiring the fake Sting. It was only after Roddy Piper figured it out, that the world was able to figure it out too.
He also helped to mastermind TNA’s Immortal group, along with Hogan and Ric Flair. In WWE, perhaps his biggest criminal act was disguising himself as a preacher for the Billy and Chuck commitment ceremony.
2 Triple H
From his earliest beginnings of orchestrating he and Mr. Perfect working together to defeat Marc Mero for the Intercontinental title to his days as ruler of The Authority, Triple H has always been The Cerebral Assassin.
He was able to orchestrate taking Stone Cold Steve Austin out of action and involve then-babyface Rikishi to take the fall for it. He also found a way to both personally and professionally marry into the family and achieve the ultimate power trip.
1 Vince McMahon
How else do you describe a man who manipulates his entire list of employees into fighting each other for his own amusement from week to week? Or how about stage his own daughter’s kidnapping and company’s hostile takeover just to strike back at one of his most hated rivals?
There wasn’t a thing that Mr. McMahon the character wouldn’t do to get a leg up and an edge on any and all rivals, and that’s how you become the ultimate criminal mastermind.
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