10 Most Embarrassing Moments Of Shane McMahon's Career

Shane McMahon has been a fixture in the wrestling world since his teenage days growing up in WWE. Vince would allow Shane to show up at shows backstage to help out in various ways. Shane wanted a hands-on role and learned the business in various tougher jobs before eventually becoming part of the on-screen product.

There have been a few less-than-ideal scenarios for Shane during his time in WWE. The challenges of working in a family business can see things blowing up in one’s face. Shane had his fair share of weaker moments outside of his highlight moves and memorable storylines. The following moments were the most embarrassing of Shane’s wrestling career.

10 Kane Electrocuting Him

The feud between Shane McMahon and Kane saw them getting quite personal. Shane returned to television after a long absence after Kane hit Linda McMahon with a tombstone piledriver. The need for revenge would see Shane taking it to Kane on many occasions.

Kane ended up getting more brutal when he attempted to electrocute the lower regions of Shane. The goal of Kane was to provide pain and prevent Shane from ever having children. WWE used to have embarrassing segments like this every other week and Shane was the target this time around.

9 "Best In The World" Trophy Win

WWE tried to add importance to one of the shows in Saudi Arabia with a tournament to name the best wrestler in the world. The finals featured Dolph Ziggler and The Miz scheduled to face off as two choices no fan would have predicted.

Shane replaced an injured Miz in the finals to make it even more bizarre. The win for Shane receiving a trophy felt embarrassing all around. WWE does deserve some credit for using it to turn Shane heel, but it was still a low moment.

8 Wrestling A Match Against God

Vince McMahon’s ego was used in the storyline during his 2006 feud against Shawn Michaels. The story of Michaels turning his life around with religion led to Vince mocking Shawn’s God in promos. There was a tag match booked between Vince and Shane vs Michaels and God.

Vince’s thinking was that God would fail Michaels and it would prove McMahon was above both the wrestler and the religious figure. WWE was very tacky with this approach and everyone involved looked like a fool, including Shane.

7 Getting Embarrassed By DX

The aftermath of Vince and Shane McMahon mocking Shawn Michaels would see him reuniting with Triple H to form D-Generation X. Fans were excited to see DX back with Michaels and Triple H directing their sense of humor at the McMahon family.

Shane was mocked when Shawn did a hilarious impression of him, making fun of the grey hair and dance skills. There were other segments that put Shane in an embarrassing situation with the worst coming when DX pumped poop all over Vince, Shane, and The Spirit squad.

6 Montreal Screwjob Aftermath

The Montreal Screwjob was arguably the most controversial moment in WWE history. Bret Hart felt Vince McMahon wronged him by lying about the finish of his Survivor Series 1997 match against Shawn Michaels and ringing the bell with him in The Sharpshooter.

Shane revealed during his podcast interview with Mick Foley that he felt Vince was right and implied Bret was wrong in the aftermath as well. Beyond the Mat cameras captured Shane right by Vince’s side, helping him limp off after Bret knocked him out. History has shown Shane protecting Vince against Jeff Jarrett, Brock Lesnar, and others, so it was likely a tough moment standing back as his dad was punched.

5 Answering Question About Triple H During Mick Foley Interview

Another memorable moment from the Shane McMahon interview with Mick Foley featured his relationship with Triple H. Mick asked about the longstanding rumors that Shane doesn’t have much love for Triple H due to his vision for WWE getting prioritized.

Shane was aggressive in his answer, not viewing the question as having any merit made the situation more discussed. The response from Shane felt a bit out of character and just opened up more questions about him and Triple H.

4 European Championship Run

The first title win of Shane McMahon came during the feud between D-Generation X and The Corporation factions. Shane was placed into a series of matches with X-Pac during the very early portion of his in-ring time.

The European Championship win of Shane would see him defeat X-Pac with outside help. Shane’s title reign felt like a joke since he wasn’t treated as a serious competitor yet. The end was even worse as Shane never even lost the title to put someone over. Shane just retired as champ with the belt going to Mideon who happened to find it in Shane’s travel bag.

3 Leaving WWE Due To Vince Picking Stephanie Over Him

Vince loves and trusts his children a lot

One of the biggest real-life dramas in wrestling featured Shane and Stephanie McMahon both waiting to see who Vince would ultimately pick as next in line. Stephanie passed Shane in the pecking order with more important roles running the show and outside branding behind the scenes.

Vince leaning towards Stephanie and Triple H as the heirs to his position was the rumored reason for Shane leaving to focus on his own business projects. Shane leaving for so many years just added more fuel to the validity of the rumors as the perception of the McMahon family inner workings.

2 Raw Underground

Shane McMahon received a negative reputation for most of his pitched ideas or new concepts for WWE ultimately failing. The most recent and high-profile instance of this came when Shane received his own segment called Raw Underground for the red brand, looking to improve ratings.

Vince approved Shane’s backstage idea that Raw Underground should feature an underground fighting segment of implied real fights instead of wrestling matches. The first week was polarizing with every week just seeing it grow worse. WWE gave up on Shane’s idea after a few months as a huge failure.

1 The Invasion

The wrestling industry’s biggest attraction ever would have been an effective WWE vs WCW storyline. Vince McMahon had the chance to make this happen when he won the Monday Night Wars and purchased WCW.

The first decision made by Vince would be one of his worst gambles. Shane became the storyline owner of WCW when he snuck in under Vince’s watch to steal the deal. The hope was that Shane would be able to lead the WCW Invasion storyline, but everything about it went poorly. This was one of the biggest disappointments to ever come from WWE and Shane was the on-screen figurehead of it.

NEXT: 10 Backstage Stories About Shane McMahon We Can't Believe