16 Must See Pictures Of WWE’s Stephanie McMahon

Being Vince McMahon’s kid must be kind of fun - and probably kind of weird - considering the business Vince has grown from a northeast territory promotion to a worldwide wrestling company. Vince’s dau

Being Vince McMahon’s kid must be kind of fun - and probably kind of weird - considering the business Vince has grown from a northeast territory promotion to a worldwide wrestling company. Vince’s daughter, Stephanie McMahon, has been able to grow up in this business, being around people like Andre the Giant, Hulk Hogan, and Pat Patterson, just to name a few. With all of this experience, it wasn’t a huge surprise when Steph became an on-screen talent back in 1999 playing the role of Vince’s “super sweet daughter” and she was pretty terrible at the role.

Like anything, it took some practice before Stephanie found her stride in the WWE, and when she turned bad by aligning herself with Triple H, that’s when she started to find her on-screen character. After taking a few breaks away from TV, she’s returned over the past couple of years to join Triple H as part of the heel stable, The Authority. During this time, she wrestled in a match against Brie Bella, and was a big part of Daniel Bryan’s rise to the top of the WWE.

Throughout the years, Stephanie has been in some interesting situations, which have been gathered and put into one convenient article. So, here are 16 must see pictures of Stephanie McMahon that include bikinis, spankings, and even blonde hair!

16 Sexy Workout


Stephanie was around thirty-seven years old when this picture was taken and she looked in amazing shape for not only 37, but after having three daughters! There are a few different pictures from this shoot, but this one is great because she’s showing her McMahon strength by lifting a giant tire – simple and effective. Every once in awhile she’ll join Triple H in his late night works that he puts out over social media.

Over the past few years, the WWE has cultivated a relationship with Muscle & Fitness as well as sending their NXT wrestlers to the Arnold Sports Festival. Triple H has always been a workout fanatic and if you follow Steph on social media, you’ll see her working out all the time. Now thirty-nine, Stephanie continues to be a shining example of taking care of herself, despite working an incredibly busy schedule. Most notably, in 2013 she involved in a WWE Fit Series training program design specifically for women.

15 SmackDown Darling


Here is a classic picture of Stephanie showing off the confidence and slight smugness that she developed once being paired with Triple H. The storyline itself was a bit weird when Triple H drugged Stephanie, took her to a drive-thru wedding ceremony, and rather than marrying Test, she got married to Triple H.

Most fans expected when she woke up, she would immediately get away from Helmsley, but instead she revealed it was a planned ceremony and her way of getting back at her father for her earlier kidnappings by the Undertaker. Undertaker attempted to crucify Stephanie, who was saved by “Stone Cold” Steve Austin. Austin was feuding with Vince at the time, so it was a huge surprise he would come out to save his daughter. Stephanie was so mad at Vince because he was aware of everything that was going on and just allowed it to happen, later being revealed as the “Higher Power” of Undertaker’s Ministry. Look, the Attitude Era had some really stupid stories, it’s best to just move on.

14 Spanking Trish Stratus


Back in 2001, the McMahon family was an absolute mess when Vince wanted a divorced from his wife, Linda McMahon. The stress from this revelation caused poor Linda to become comatose and confined to a wheelchair. For a few weeks, she would just stare off into the distance and she was wheeled all over the arena. Since Linda was clearly out of commission, Vince then engaged in a very public affair with the relatively new WWE Diva, Trish Stratus. It was pretty obvious Vince enjoyed his time with Trish, so he booked himself in some pretty sleazy segments with the former Women’s champion.

Stephanie was so mad at Vince about this; she ended up having a match against Trish, which for the most part was a terrible match. Mid-way through, she ended up pulling down Trish’s wrestling tights and spanking her, much to the crow’s delight. Towards the end, General Manager, William Regal, made his way out and assisted Stephanie to get the victory.

13 Blondes Have More Fun


Steph’s natural hair color is dark brown, but around 2005, she made some random appearances, and when she did show up, she decided to change things up a bit and go blonde. Of course, this blew fan’s minds because it looked so different from the appearance they were accustomed to. Ultimately, the look didn’t last too long, not sure if it was outside opinion or just Steph wanting to try something different.

As mentioned, Steph wasn’t really on TV during these years since as she was busy getting married (for real) to Triple H and starting a family. Even though she wasn’t on TV for these few years, she was very much in the backstage area working as a Director for Creative Television. Basically, she was one of the higher-ups that decided what went on WWE TV, in particular, on SmackDown as Vince still held power over what went on Raw. So what do you think: does brunette or blonde suit Stephanie better?

12 SummerSlam Match


Brie Bella took on “The Billionaire Princess” at the 2014 SummerSlam PPV, mostly to defend the honor of her husband, Daniel Bryan, from The Authority who tried to stop him from becoming WWE champion any chance they got. This was the first time in ten yearsStephanie had wrestled in a match, and she took it very seriously, working out daily (often sharing videos with fans) to get ready for it.

The big ending was when Triple H came down to the ring, followed by Nikki Bella. Triple H tried to interfere, but was knocked to the floor by Brie. Nikki then jumped in the ring and at first it looked like she was going to help Brie win the match, but instead she blasted her sister with a nasty forearm, turning heel, and allowing Stephanie to go on and win the match via using Triple H’s finisher, the Pedigree.

11 You’ve Changed


At some point during her earlier on-screen run, Steph decided she needed breast enhancements, which is pretty typical in the WWE environment. Although, it’s one thing to get some work done, but she went from being on the fairly small side to get humongous implants, seemingly overnight. This change didn’t just get the fans talking, but wrestlers had to bring attention to it, as well. The one who talked the most was one of Stephanie’s biggest rivals, Chris Jericho, who mentioned the changes almost every time they interacted on TV.

Jericho would throw out lines like this every week: “Thanks Stephanie, you’re the breast… I mean best!” Never said the jokes were intelligent, but he was unrelenting on her, which made for some pretty entertaining TV, her reactions were always on point and would get the crowd to pop, which is just a testament to her ability to do whatever is necessary to make the product better.

10 Getting Arrested


During an episode of Raw, Brie Bella was forced to watch the show at ringside with the rest of the crowd thanks to being banned from being backstage. Her rival at the time, Stephanie McMahon, came down to where she was sitting and decided to not only mock Brie, but talk a little trash in the process. Brie had enough of the harassment and called Steph a “B****” causing people right around her to go ballistic, seriously look that segment up, the crowd reaction is hilarious.

Steph was not a fan of that and ended up slapping Brie in the face for her comments. Soon afterwards, two officers came ringside and told Stephanie that she was being arrested for battery. She promptly lost her mind, yelling at everyone – including the cops – telling each one that she will have their badge! Triple H showed up to try and help, but off she went in the paddy wagon.

9 Mud Bath


Wife of the later Eddie Guerrero, Vickie had worked for the WWE since 2005. In 2014, it was announced she would be leaving the company for good to move on to some new life ventures. On her last segment, Vickie was to fight Stephanie in a mud bath match, and if she lost, she would be “fired.”

Initially, Steph sent out some hench-women (Alicia Fox, Layla, and Rosa Mendes) to take care of Vickie, but she fought back and threw all three of them in. While being distracted, Steph sneak attacked Vickie, sending her into the mud, and winning the match. Stephanie then taunted her, until Vickie had enough, grabbed her, and threw Steph face first into the pool of muck. Steph hammed it up for awhile by slopping around in the mud just like her father. Out of anger, she threw an unlucky referee into the pool, eventually Stephanie managed to climb out as the crowd chanted “You suck!” to her.

8 Hammer Time


Stephanie came out to the ring to cut a promo on Sting (the wrestler, not the singer), and basically tore him apart, like she tends to do to most other wrestlers. For the big exclamation point, she went to slap his face, which he caught in time. Fear suddenly came over Steph’s face, which promptly brought Triple H down to the ring to help his wife out, even though she totally brought this on herself.

During his entrance, Stephanie bailed out of the ring as Triple H jumped up on the apron. At this moment, Steph reached under the ring and slowly rose with that evil look on her face, holding Triple H’s signature sledgehammer. Apparently, this was a nod to her father, who rose up from the floor in the same manner, but his face was all bloodied at the time. She handed the sledgehammer off to him and Triple H went in to confront Sting and his own signature weapon, the baseball bat.

7 Attacking Paul Heyman


On the 1000th Raw, Paul Heyman was in the ring talking trash to Triple H, the usual stuff was no big deal, but then he started ripping on his kids and family. Out of nowhere, Stephanie McMahon came out from the back to confront Heyman. At this point in time, she wasn’t on-screen often, so it was a huge surprise to see her come out and tear down Heyman.

After crushing Heyman’s soul, she slaps him in the face, which causes Heyman to mention her kids, yet again. This send her into a rage as Stephanie lunges at him, tackling Paul to the mat with multiple slaps to the head and punches to the ribs. She continued on until Brock Lesnar ran out to save his manager. Aside from this on-screen fight, it seems like Paul and Steph have never really seen eye-to-eye when it comes to the wrestling business, two different outlooks has been known to cause tension in the past.

6 Hitting The Runway


Here is something non-wrestling related, Stephanie was asked to come to a New York fashion show held by Strut. This particular show was called “Moms on a Mission” and it was celebrating women who were not only mothers, but were making a difference, whether they were entrepreneurs, CEOs, or philanthropists in their professional lives.

The show also included some other celebrities, all of who got to walk up and down the runway, some did it with their kids, while others went solo. Stephanie went on her own as she rocked it in a classy black dress and black heels, looking as awesome as ever! As Chief Brand Officer, she’s trying to push WWE’s product out to new venues as a way to bring in new fans by getting involved in more opportunities like this one. She has a tough balance of being involved in events like this to help promote WWE, while also being a terrible person (most of the time) on TV.

5 Almost Married "The Deadman"


“The Billion Dollar Princess” was introduced to the WWE Universe as Vince McMahon’s innocent daughter; she was about as babyface as you could get, we’re talking John Cena level. This was all well and good until The Undertaker and his ministry got involved with her. They ended up kidnapping Steph, later bringing her out to the ring and attempting to crucify her on Undertaker’s symbol as a starting point to the wedding ceremony between Steph and The Undertaker.

Luckily for her, people like Ken Shamrock, Big Show, and “Stone Cold” Steve Austin couldn’t stand by and watch this happen. Austin cleared the ring completely and Stephanie gave him a huge hug for saving her, which he didn’t reciprocate, because he hated Vince McMahon so much. It was later discovered that Vince was Undertaker’s “Higher Power” and actually allowed her to be kidnapped and nearly married away. Vince did not win “Father of the Year” for those actions.

4 Corporate McMahon


Throughout the years, Stephanie has not only grown up in the business, but worked her way up the corporate ladder, starting out as an account executive and receptionist at age twenty-two. She was then moved into the creative department, initially as a Director, and then a Senior Vice-President. Here, she was a major part of the story lines that you all saw on TV in the early to mid 2000s, in particular, onSmackDown.

From 2007 until 2013, she was promoted to Executive Vice-President of Creative Development and Operations, which basically gave her oversight of all live and televised events, including how the shows were booked. Currently, she is the Chief Brand Officer and helps push the WWE brand towards third-parties including advertisers, charities, media, and investors. In the last few years, you’ve probably noticed WWE get much more involved in charities – that’s been primarily her work to get more positive attention towards the WWE.

3 Women’s Champion


Somewhat surprisingly, she’s held the Woman’s title only once in her career and that was way back in 2000. The win came when she defeated Jacqueline (thanks to some outside help by Tori of DX) on an episode of SmackDown. During her reign, it was typically known as the “McMahon-Helmsley era” since Steph held the Woman’s title, and Triple H held the WWF Championship, both wrestlers dominated the competition for a long period of time.

She remained champion for 146 days and lost it on Raw to Hall of Famer, Lita, The Rock was the special guest referee for this match. If you never saw any of her matches, consider yourself lucky, they were pretty bad – wrestling is not one of her strengths. She had the skills to get through a match, but for the most part the moves were pretty basic and usually broke down to a cat fight-like brawl between the two wrestlers.

2 Younger Days


Here is a picture of Steph at a party with her mother, Linda McMahon. This was taken some time before she debuted on-screen for the WWE, before fans even knew about “The Billionaire Princess.” Even though 1999 was her official on-screen debut, there’s plenty of WWE merchandise catalogs where Steph modeled the different wrestling merchandise for the company.

Unlike her brother Shane McMahon, who left the company years ago to help run an On-Demand company in China, Stephanie has literally worked for the WWE her whole life. Although, when injuries ravaged the roster, Shane did return at WrestleMania 32 to have a match against Undertaker in a Hell in a Cell match. Even though Shane lost the match, he was so popular with the fans, they decided to keep him around for a little while longer. Currently, he’s co-running Raw with Stephanie and with a potential brand split, it’s possible he could be running either SmackDown or Raw in the future.

1 The Power Couple


For a long time the WWE kept it a (very bad) secret on-screen that Triple H and Stephanie were actually married in real life, but over time that topic was less and less avoided. Today, the tandem is known as “The Authority” and it’s usually brought up in story lines that they are together. At 46, Triple H still wrestles sporadically, was not long ago the WWE champion, and was able to main eventWrestleMania 32 against Roman Reigns.

He’s also been an integral part of expanding WWE’s developmental promotion (NXT) by reaching out to all parts of the world for talent, very recently signing their first Chinese-born wrestler. He’s also expanded WWE’s reach into the indies like working with EVOLVE as a way to see potential future talent without actually having to sign them to a deal with the WWE. Triple H continues to bring in veteran indy talents like AJ Styles, Samoa Joe, Eric Young, and Austin Aries, further tightening WWE’s grip on the wrestling world.


Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Wrestling

16 Must See Pictures Of WWE’s Stephanie McMahon