5 surprising WWE Superstars who lost to Vince McMahon

Vince McMahon, the Chairman of WWE, has handled the company's reins for the last 39 years. While some of his recent booking decisions have faced criticism, it is impossible to ignore his revolutionary actions to modernize the professional wrestling business.

McMahon initially wanted to be a wrestler, but his father told him to stay away from the ring. He handled commentary duties for decades before pioneering the evil boss persona in the industry. Mr. McMahon was reckless and over-the-top. His rivalry with Stone Cold Steve Austin is widely considered as one of the greatest in WWE history.

Like most members of the McMahon family, Vince McMahon entered the ring on multiple occasions and defeated many of his opponents through various shenanigans and interferences. He even won the WWE Championship at one point.

McMahon's greatest victory was in Backlash 2006 when he defeated Shawn Michaels and "God" in a tag team match, excluded from the list for logical reasons. Here is a list of 5 surprising WWE Superstars who lost to the company's chairman.

---

#5 Former WWE Intercontinental Champion Ken Shamrock

A pioneer of MMA, Ken Shamrock successfully transitioned to the professional wrestling industry. He popularized the Ankle Lock and won multiple championships in the company.

But his legitimate fighting background was not enough to defeat Mr. McMahon. Shamrock was part of The Corporation, but the chaotic storyline saw Shamrock facing Vince McMahon in June 1999.

The match was forgettable. Jeff Jarrett attacked Shamrock before the match while McMahon defeated him with the Ankle Lock in seven seconds.

However, the episode of Monday Night Raw remains memorable for Vince McMahon's declaration of being the mysterious Higher Power.

#4 Former WWE Champion The Rock

The Rock enjoyed tremendous success in WWE, becoming the most successful Anoa'i family member in the industry. Like most top stars of the Attitude Era, even The People's Champion could not escape a loss to Vince McMahon.

The Rock teamed up with The Brothers of Destruction to face Vince McMahon, Shane McMahon, and Triple H. While The Rock, Undertaker, and Kane held their own against interferers trying to help the McMahon-Helmsley Faction, McMahon won by pinning The Rock.

---

#3 Former WWE Champion John Cena

WWE advanced a rivalry between Bret Hart and Vince McMahon in 2010, despite Hart not being a full-time wrestler for years. John Cena supported The Hitman and faced the wrath of Mr. McMahon.

The company's Franchise Player was punished through a one-on-five handicap match against Vladimir Kozlov, Mark Henry, Jack Swagger, Drew McIntyre, and Vince McMahon. After the others weakened Cena (except for a conflicted Mark Henry), Batista inflicted more damage on him, Henry, and Kofi Kingston.

Vince McMahon capitalized on Batista's attack to pin his company's poster boy.

#2 WWE Hall of Famer Ric Flair

Ric Flair is widely considered to be one of the greatest professional wrestlers of all time. Wherever he wrestled, he was promoted as a top star, including the Vince McMahon-led WWE.

A rivalry between McMahon and Flair saw them fight for kayfabe ownership of WWE. Vince wanted to regain full ownership of the company and faced The Nature Boy in a No Holds Barred match.

The Nature Boy dominated much of the match, but yet again, an interference saved the day for Vince McMahon. A young Brock Lesnar interfered, leading to the former to win and regain 100% ownership.

---

#1 WWE Hall of Famer Stone Cold Steve Austin

The rivalry between Stone Cold Steve Austin and Vince McMahon was one for the ages. Employed workers in the crowd saw themselves in Austin and enjoyed how he challenged his evil boss' authority.

Austin faced McMahon and five others in a gauntlet match during the St. Valentine's Day Massacre build-up. The future Hall of Famer lost the match.

However, he won a vital Steel Cage match against Mr. McMahon when the debuting Paul Wight inadvertently helped him triumph.