The Most Confusing Things About Stephanie McMahon's Career

"The Billion Dollar Princess" Stephanie McMahon was born into the wrestling business with a silver spoon in her mouth, and got involved with working in the then-WWF at a very young age. At just 13 years old, McMahon started modeling WWF merchandise for various magazines. It didn't take long for the fourth-generation McMahon to find her way into the thick of the wrestling world, however. After graduating from Boston University, her life with WWF began full-time as an account executive for the offices in New York. From there, McMahon began working her way up the corporate ladder, a journey which also led into becoming her own character on television.

Over the years, McMahon has held various positions within the company, both on television and on the corporate level that often had her on the road with the company and its stars instead of sitting in the office in Stamford, Connecticut. Inside the ring, McMahon has been involved in everything from the Invasion angle, to playing the general manager of both "WWE SmackDown" and "WWE Raw," to even finding real-life love onscreen.

While all of McMahon's accomplishments outside the ring have been more than noteworthy, and have helped etched her name into the annals of WWE history not just because of her last name, sometimes, the way she's gone about them have been confusing for fans watching from the outside. Her ventures in the ring have been even more so throughout her career, though she even held the Women's Championship at one point. From strange allegiances, to questionable booking decisions, and life beyond the mat, there are a few instances of McMahon's already lengthy career that have been more than confusing to fans over the years. 

Being the "Billion Dollar Princess" didn't come without its occupational hazards, initially. McMahon's first time on WWF television, at just 23 years old in 1999, had her involved in a truly bizarre storyline with The Undertaker and his Ministry of Darkness, as well as her own father, then-chairman of the company, Vince McMahon.

Undertaker and Vince were locked in a bitter feud, which led to the Ministry kidnapping the boss' daughter. Stephanie played the "damsel in distress" role perfectly, leading to a now-iconic image of her being strapped to a cross bearing the Undertaker's insignia right before "The Deadman" attempted to force her to marry him in an "Black Wedding" ceremony performed by Paul Bearer. Her father's arch enemy, "Stone Cold" Steve Austin ended up saving the day. The feud in itself was initially confusing to fans, as Austin and Vince were the primary feud, and Undertaker seemed to come second in Vince's mind, up until the kidnapping of his daughter.

If the kidnapping and forced marriage angle wasn't weird enough for fans, it would be later revealed that Vince was the leader of Undertaker's Ministry. Meaning, it was Stephanie's own father who had Undertaker kidnap the 20-something, to marry into his cult.

While McMahon's real-life marriage to Paul "Triple H" Levesque may not be confusing in and of itself, it's partially how their courtship got started that has some fans perplexed to this day. Triple H and McMahon were paired in storyline when she was slated to marry her then-fiancé Test. Triple H interrupted the wedding ceremony and revealed a video of a drugged McMahon in a convertible beside him, going through a drive-through wedding chapel in Las Vegas. The pair then soon officially united to start the McMahon-Hemsley era, to the dismay of McMahon's father, who was then out with injury. The confusing aspect around the start of their storyline, was the fact the pair began dating in real life sometime in 2000, seemingly around the same time Triple H was still seeing fellow D-Generation X member Chyna. Depending on who you ask, their relationship ultimately led to Chyna leaving the company in 2001.

Over the years, the couples' relationship in storylines confused fans, from a love triangle involving Kurt Angle, to confusion when Triple H returned as a triumphant babyface in January 2002 while his wife remained a heel, to an in-ring wedding where Triple H kayfabe dumped his real-life girlfriend the following month when she was revealed to have faked a pregnancy.

Triple H and McMahon officially wed in 2003, but their marriage was not acknowledged on WWE programming until six years later when they formed the "Authority." The first time the company made any references to the now-married couple prior to The Authority was in 2006 when Triple H and Shawn Michaels reunited to form D-Generation X. Known for jokes involving breaking the fourth wall, one such gag included a jab made about McMahon's baby looking like him after Triple H missed a "Raw" due to his wife giving birth.

Chris Jericho's first true main event angle in the WWF was alongside Stephanie McMahon, when she and Triple H were the baddest heels on the roster around 2000. McMahon became the target for crude insults from Jericho from the beginning, with Jericho being one of the first faces to tell off the boss' daughter in such a way. He went as far as to have a "Planet of the Apes" monkey pie her in the face, as well as embarrass her by calling out her breast implants. The pair had numerous promo battles, where Jericho almost always got the upper hand against McMahon. Jericho's insults against McMahon culminated in 2000, when he was involved in a Last Man Standing match against Triple H, who was looking to defend his wife's honor.

However, it became confusing when McMahon decided to align herself with Jericho and become his manager after being dumped in storyline by Triple H, in the angle where she claimed to be pregnant, but wasn't. The alliance got even more confusing when Jericho lost to Triple H at WrestleMania 18, despite McMahon's attempted interference.

This led to a bizarre triple threat match on "Raw" between all three, McMahon included, for the Undisputed Championship. There was a stipulation put in place before the bout that if McMahon was pinned, she would be forced to leave the company. She ended up being within one count of being the first female WWE Champion, but was pinned by her husband.

Before the shocking and disturbing real-life allegations were made against her father involving sex trafficking and abuse, Stephanie McMahon and Vince McMahon had a confusing onscreen relationship throughout most of the former's career. Outside of her debut angle involving her father technically being the person to demand Undertaker's kidnapping of her, McMahon later sought to spite her father by marrying Triple H following their Vegas nuptials. However, after McMahon and Triple H had taken the helm of the WWF while Vince was out with injury, McMahon reunited with her father and brother, Shane McMahon, at WrestleMania 2000, where they helped Triple H defend his championship.

Even after reuniting with her father, one of the most egregiously confusing examples of their onscreen relationship was Vince's affair with Sable in the summer of 2003, which his daughter resented. The feud culminated in a father-daughter "I Quit" match at No Mercy, where Vince choked Stephanie with a lead pipe, leading to her mother, Linda, throwing in the towel, causing her to lose the match.

Most recently, in 2016, Vince made things more confusing with his daughter, when he presented her with a "legacy of excellence" award, before Shane returned and demanded control of "Raw" from Stephanie. Vince accepted, pitting Shane against Undertaker at WrestleMania 32 for control. Vince then opened the "Raw" after the show to announce Shane would be running his sister's show for "one night only," but the older McMahon sibling continued to run "Raw" due to "overwhelming fan support." At the end of the angle, it ended up being both siblings running the show. Stephanie and Vince's onscreen relationship has been strange, confusing, and murky, at best, for almost two decades before both stopped making consistent television appearances.

McMahon has been involved in the corporate side of WWE for over two decades. She worked her way up the ladder to eventually become chief brand officer in December 2013. There, McMahon spearheaded efforts to help WWE's brand reputation among advertisers, business partners, investors and more, and served as the lead ambassador for the company. However, around the time accusations against her father regarding "hush money" payments paid to former employees became public, that's when things regarding McMahon's position in the company also started to get confusing.

In May 2022, McMahon announced via X that she would be taking a leave of absence from the majority of her duties with WWE to focus on her family. Less than a month into this leave, however, Vince stepped away from his role as chairman and CEO of WWE due to the hush money allegations. McMahon was named interim chairwoman and co-CEO, alongside Nick Khan, of WWE following her father's "retirement." At the time, McMahon said she would hold the role until the investigation into her father concluded.

To further muddy the waters, in January 2023, Vince came out of retirement and reinstated himself to the WWE Board of Directors prior to WWE's merger with UFC to form TKO Group Holdings. Less than a week after the announcement that her father was returning, McMahon resigned her post as co-CEO. She once again announced the move via her X account, saying it was a privilege to serve. Since then, McMahon has made sporadic appearances within WWE. She was most recently seen by fans at WrestleMania 40 to open the show, and also appeared to announce picks in the 2024 WWE Draft. The future for McMahon in WWE in uncertain, as it has also been alleged Stephanie is listed as "Corporate Officer #3" in former employee Janel Grant's abuse and sex trafficking lawsuit.