Mr. McMahon is not the man to mess around with, as many superstars in the history of WWE, has learnt it the hardest way. The ones who are in the list had experienced the most disgusting things in their life. Or to put it simply he had gone so far to trap to ensnare the superstars who have dared to defy him. Some of them incidentally got their payback in return but crossing the boss was never easy as though some has done it in their own way to find themselves in the chairman’s bad book.

Top 10 superstars Mr. McMahon hated the most and did humiliating things with 1

 Top 10 superstars Mr. McMahon hated the most and did humiliating things with 2

 

Daniel Bryan

Bryan had much going on with his son-in-law rather than the boss himself. Back in summer 2013, he was handpicked as the number one contender for the WWE championship but that was opposed thoroughly by Vince McMahon who had enough reasons not to call a savage dressing goat face the “WWE champion.” Nothing was physical in this case but troll was trending for Bryan.

 Top 10 superstars Mr. McMahon hated the most and did humiliating things with 3

The Undertaker

It was complicated between both the devils. While the ministry of darkness was controlled by the chairman himself at one point, there were times when the boss’ daughter was forced to be the Phenome’s infernal bride. That was the time when he faced the chairman in a buried alive match but lost the battle. You decide who is more evil?

 

D-Generation X

Quite awful, but his in law fits into the list. Triple H had made it personal to torment his father in law as the ringleader of D-Generation X. Back in the attitude era, he set up wedding ceremony with Stephanie only to perform the crotch chops on Mr. Mcmahon whereas he reunited once again with Shawn Michaels and did some horrible offenses like painting chairman’s plane and the headquarters’ of WWE.

 Top 10 superstars Mr. McMahon hated the most and did humiliating things with 4

Trish Stratus

It was one of the most disgusting displays in television history. Though it was done in a storyline purpose, still a Hall of Famer like Trish Stratus does not deserve to be treated like that. McMahon had forced the greatest Diva in history to strip down, bark like a dog in a televised episode. It showed how low a man can go to punish the woman who did not have respect for her anymore.

 

Ric Flair

Imagine the scenario, Mr. McMahon riled up losing all his powers. Only Ric Flair managed to do that and that too for an extended amount of time. It was revealed that Stephanie and Shane sold their stake in WWE in the Flair ‘consortium’ which made a WCW/ECW alliance. In other words, Flair became the co-owner alongside him, which is not at all the ideal situation for the boss.

Top 10 superstars Mr. McMahon hated the most and did humiliating things with 5

Roman Reigns

“Anyone but you, Roman” was originally declared by Bray Wyatt but taken too seriously by the boss himself after he battled almost everyone to reach to the top of the mountain. In order to repay Roman for his attack on Triple H and himself, the boss is strict to set up the “one versus all” motto and declared to defend his title in the Royal Rumble match itself. The confrontation is far from over, though, coming weeks will show some new chapters in the rivalry.

Hornswoggle

Mr. McMahon’s greatest enmity was reserved for the kids. That reached the height though after he found that Hornswoggle was carrying an undetected blood of a McMahon. Molding the smallest superstar in WWE superstar became his motto since then. Entrusting him to Carlitto, beating him up in a steel cage or even forcing him to kiss his ass was the actions taken. He turned out to be Finlay’s kid, though.

Top 10 superstars Mr. McMahon hated the most and did humiliating things with 6

Randy Orton

A mind boggling fact is that the McMahon’s had made several allies with WWE’s Apex Predator and every time the ally had broken, Randy terrorized both the boss and his broods. Mr. McMahon had plenty of blooded moments with the 12-time world champion including a punt to the head in 2009 moments after questioning the worth of Stephanie McMahon as an heiress and human being. But then, Orton never did get along well with the others.

Bret Hart

The complicated relationship between Bret and McMahon just got out of the hand at the Montreal Screw Job and it was meant to be that way considering the peeled back, layer by layer rivalry between the two. The Excellence of Execution and the Chairman, both were clashed by tremendous egos from the get going in the business which ultimately got under the bridge in a match at Wrestlemania 26 but not before tasting some bad blood with chair shots.

Top 10 superstars Mr. McMahon hated the most and did humiliating things with 7

Stone Cold Steve Austin

No special prize for guessing this one. Ask anyone to get their hands on the boss and the situation will resemble with the War that Stone Cold was against the chairman. The Rattlesnake’s clash with his boss spanned the better part of a decade with several twists and turns where we had seen Mr. McMahon’s rancor for Austin led to hirings, firings, screwjobs, beer baths, beatdowns, tumbles through tables and much more. Even these days sitting in the Stone Cold podcast gave us goosebumps thinking of the moments we had back in the attitude era. Surely, some things never change.

 

Arindam Pal

A WWE writer passionate about the sports.

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