Stephanie McMahon is a very polarizing figure in the wrestling business. Her intentions always appear to be in the right place and she says the right thing just about every time she is interviewed about the state of WWE and how it's being run. Her on-screen work is superb as a tremendous heel character that would succeed on any television show, let alone in professional wrestling. However, there is a side of her we don’t see that often provides negativity in the wrestling business.
Stephanie is a shrewd businesswoman that learned from her father and shows no mercy in getting ahead. Many wrestlers and fans complain about how she always stands tall on screen and no one can ever truly get revenge on her, since the men can’t hit the women and the women’s wrestlers don’t work against Stephanie in matches. There’s also the allegations of hypocrisy, as many have said she's a mean spirited person behind the polite smile and PR comments. Stories have surfaced through the years of her friends seeing Stephanie’s loving side and her enemies seeing the vindictive boss. We'll look at both sides of Stephanie McMahon’s relationships with eight of her closest friends in WWE history and seven wrestlers she despised.
15 Close with: Charlotte Flair
The friendship between Charlotte Flair and Stephanie McMahon sees them share the similar background of having to follow in the footsteps of their legendary fathers. Vince McMahon is the iconic owner and promoter of WWE that Stephanie is trying to succeed. Charlotte is doing the same as she continues the Flair legacy created by her dad, Ric Flair.
14 Despises: Kaitlyn
One women’s wrestler that got on the bad side of Stephanie McMahon was Kaitlyn. The former Divas Champion apparently crossed Stephanie backstage in an incident that would eventually play out on the screen. Kaitlyn allegedly approached Stephanie to ask her something while McMahon was having a conversation with someone else. This led to Stephanie apparently causing a scene and talking down to Kaitlyn backstage.
13 Close with: Big Show
Big Show has been in WWE for eighteen years now and has remained a loyal employee. The big man doesn’t mind taking a backseat to the new talent, but will still appear on the live events and promotional tours to help the company. It comes to no surprise that Show is a good friend to all members of the McMahon family.
12 Despises: Scott Steiner
Scott Steiner’s singles career in WWE was a huge failure that went by faster than anyone could have expected. The WCW legend returned to WWE to a massive ovation at Survivor Series 2002 that showed the fan base loved him. Steiner’s return storyline saw him choose between Raw and SmackDown brands with General Managers Stephanie McMahon and Eric Bischoff vying for him.
11 Close with: Lita
Stephanie McMahon became close with many of the wrestlers from the Attitude Era and kept in touch with some of them. Lita and Stephanie have always claimed to be friends with positive words always being exchanged. The latest push of women’s wrestling in WWE is partially due to Stephanie wanting to be the figurehead of equality in the company.
10 Despises: Christy Hemme
The firing of Christy Hemme by WWE was one of the more shocking decisions at the time. Hemme won the first Diva Search contest and was rather popular with the fan base. There was potential there and she continued to gain popularity. WWE letting her go in less than two years meant there had to be some smoke where there was fire.
9 Close with: Shawn Michaels
Triple H’s friends have become Stephanie McMahon’s friends through the years, especially since they all work together. Michaels is the one member of The Kliq that has remained in WWE through the years and completely cleaned up his life.
8 Despises: Rob Van Dam
Rob Van Dam struggled to succeed in the political landscape of WWE. Stephanie McMahon was one of the people that didn’t like Van Dam and it likely hurt his career. His attitude saw him play a strangely laid back role backstage while everyone walked on eggshells. Stephanie didn’t like his attitude and she absolutely despised his hobbies.
7 Close with: Mick Foley
The friendship between Mick Foley and Stephanie McMahon has lasted for almost two decades now. Foley wrote a blog stating a major reason for him taking the on-screen role of Raw General Manager last year was getting to work with Stephanie. Mick cut a promo on Raw where he recalled meeting Stephanie as “the girl with the shy smile” on the night of his infamous Hell in a Cell match with The Undertaker and it was a true story.
6 Despises: Paul Heyman
Paul Heyman and Stephanie McMahon had one of the most understated backstage rivalries in WWE history. They started working together backstage when putting together the SmackDown shows following the brand split. SmackDown received rave reviews under the direction of Heyman leading the staff. Stephanie often butted heads with him and rumors leaked at the time that they would get into shouting matches during booking meetings.
5 Close with: The Rock
Another Attitude Era friend that Stephanie McMahon still has today is The Rock. Stephanie’s early career saw The Rock become one of her first rivals on the microphone. The Rock would tear her down once she became an evil heel that fans loved to boo. Their friendship would form through the bond of working together in front of thousands in the arena and millions on television.
4 Despises: AJ Lee
AJ Lee is one the very few performers to publicly speak out against Stephanie McMahon while working for WWE. The bad blood started due to Lee’s husband's, CM Punk, ugly relationship with Stephanie’s husband, Triple H. Both wives apparently held on to the personal grudge. Stephanie and AJ had a few on-screen segments that often saw Stephanie talking down to the Divas Champion.
3 Close with: Brie Bella
Stephanie McMahon has only wrestled one match on WWE television over the past thirteen years. The surprising choice for her opponent was Brie Bella at SummerSlam 2014. It made sense because Brie’s husband, Daniel Bryan, feuded with The Authority for many years ,but it was such a rare opportunity. Stephanie is the most hated female heel in the company and she just doesn’t wrestle.
2 Despises: CM Punk
There is no one in WWE that Stephanie McMahon has ever publicly shown more contempt for than CM Punk. Everyone knows Punk hates how the company is run and he absolutely loathes Triple H. That has led to fans chanting “CM Punk” at Triple H, Vince McMahon and Stephanie any time Raw is in Punk’s hometown of Chicago, Illinois.
1 Close with: Trish Stratus
Trish Stratus and Stephanie McMahon are extremely close friends that have been bonded together since the days of the Attitude Era. They had a great match together at No Way Out 2001 and their chemistry played a huge role in the Vince McMahon vs. Shane McMahon storyline at the time. Both women benefited greatly and went to the next level as performers by working against each other on-screen.
The friendship of Trish and Stephanie went understated until the news of Trish entering the 2013 WWE Hall of Fame broke. Everyone expected Lita to be the one to induct Stratus, considering they are real-life best friends and had a legendary rivalry. Stephanie ended up being the one to induct Trish and clearly wanted the honor. Stephanie's speech saw her speak lovingly about one of her best friends in the wrestling industry.
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