It was quite the road for Stephanie en route to her WWE success. Using Stephanie was never in the cards, especially when it came to her father. It was Vince Russo that nudged the idea and boy, was he ever on the money. Stephanie went from being an Accounting Executive at the WWE HQ in New York to making a debut on-screen, in a story involving Undertaker and Stone Cold.It was her heel turn in late ’99 that changed everything. Once she turned on her dad and joined Triple H, Stephanie would grow into one of the most recognizable WWE faces.

This article deals with everything prior to that moment. The list features rare photos of Stephanie before her fame. Enjoy the article folks…let’s get started.

One-on-Ones – Stephanie McMahon

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15Selling The Merch

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Stephanie started at a young age, working the old WWE catalog in the merchandise section. Man, times were different back in the day. The only way to buy merchandise was at a show or by ordering it through the WWE magazine.

She’s wearing “The Rockers” merchandise in the pic above. Who would have thought that the dude on that t-shirt would align with her future husband years later.

14Daddy’s Girl

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Stephanie was always daddy’s little girl, both on-screen and behind the scenes. Despite Vince’s hectic schedule throughout the years, the two managed to stay very close.

In the early 2000s, Stephanie would change her position in the company, becoming the head of the creative writing team. She’s now the brand ambassador and who knows, maybe the company might be hers one day.

13XFL Interviewer

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The XFL completely tanked in its inaugural season. A big problem was the similarities with the WWE product. From Jim Ross to Stephanie McMahon, it included one too many familiar faces.

Vince also tried reaching a little too much by issuing locker room rumors. Let’s hope he doesn’t go down this path again with the XFL re-debut.

12Backstage With Dusty & Sapphire

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A rare picture of Stephanie back in her earlier days. She was likely attending high school at this point. Chances to take part in WWE events, by hanging out backstage, were few and far between.

We have a rare shot of Stephanie alongside Dusty and Sapphire. Dusty would go on to make quite the impact with WWE, behind the scenes, alongside Triple H’s NXT.

11TV Debut

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Stephanie posted this photo to her IG account. It was a special moment for McMahon since she was making her on-screen debut. It was a small role as Stone Cold searched for The Undertaker – McMahon played innocent during the segment.

Just a couple of years later, that same character would be molded into one of the better heels of the 2000s.

10The Girl With The Shy Smile

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A throwback pic from 2000, featuring Mick Foley and Stephanie McMahon behind the scenes. Mick referred to Stephanie as “the girl with the shy smile”. At this point, Stephanie was just starting to break out with her character on-screen, siding with Triple H.

She would also cause some tension due to her real-life relationship with Triple H…one that didn’t sit well with the boys.

9Playing With Dad

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She’s having fun with her pops in the picture above. Who would’ve predicted that these two would have squared off years later, in an actual match!

Stephanie’s character was essentially written off, as she took on her own father at No Mercy. We still can’t believe this match went down.

8With Test

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Stephanie was used alongside Test early on, prior to her fame. As mentioned earlier, it was a move to elevate Test, though, on the contrary, it elevated Stephanie, who would become a massive star shortly after!

Test would go on to a decent career, but nothing compared to what was projected for the big man.

7Joining The Game

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This move changed everything for Stephanie’s career. She joined forces with Triple H, surprising everyone and turning heel. The pivotal turn took place at Armageddon, as Stephanie aided Triple H in his battle against her father.

It was a career-changing moment for Stephanie, who never looked back after that.

6With André

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Throughout her childhood, Stephanie always had a soft spot for André. He made frequent visits to the house – Steph considered André to be one of her best friends.

Given his age, Vince lessened André’s matches during the final part of his WWE run. Some say that it hurt their relationship.

5Big Brother

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Shane would join WWE a little bit earlier. One of his many roles early on included working as a referee.

Shane has lots of stories from their youth, including throwing his own dad in the pool when some of the boys were at the house. Of course, Shane left the house right after pushing his dad.

4Alongside Mom

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Another forgettable WWE moment featured Stephanie McMahon feuding with her own mom. She has two regrets in the business…one was kissing Eric Bischoff and the other, slapping her mom for storyline purposes.

It created monster heat for Stephanie and, without a doubt, it must’ve been tough to go through with.

3Baseball With Dad

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She’s playing baseball with dad – given his crazy schedule, such moments were valued by Stephanie and Vince.

Vince never really hesitated when it came to including the kids in WWE programming. As mentioned earlier, Stephanie would also take on a big role backstage, in the early 2000s, as a lead writer.

2More Shane Throwbacks

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It is only fitting that these two would also go on to feud on-screen during their WWE careers.

Most recently, the feud would begin with Stephanie taking control of RAW, while Shane took over SmackDown. Nowadays, both are taking a hiatus from on-screen duties, with Shane recently appearing on NCIS.

1Last One

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Stephanie wasn’t given a WWE position without the proper education. She graduated from the University of Boston with a degree in Communications.

She would start working for WWE in ’98, at the head office, as a receptionist. Later, she would be the Accounting Executive for the company, at the HQ in New York.

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