Every once in a while, a rivalry develops between a wrestler and another wrestling personality. Hulk Hogan had Bobby Heenan, Ric Flair had Eric Bischoff, and Stone Cold Steve Austin had Mr. McMahon.
Chris Jericho has had wars with several rivals in WWE, WCW, ECW, and AEW. Most famously, Jericho defeated The Rock and Stone Cold Steve Austin on the same night in 2001.
However, most of these wars were in the ring; there is one war on the mic that defined his career. That was the war of words with Stephanie McMahon.
If you were a WWE fan in the Attitude Era, you know where I am going with this. Not only did it elevate Y2J’s career, but Stephanie McMahon also took her place as a Hall of Fame heel.

Y2J Arrives in WWE
Chris Jericho debuted in 1999. He was going to kick off the new millennium. After some time in WCW as the cruiserweight champion of champions, Jericho decided it was time to seek other opportunities.
It was a hot night in Chicago when the millennium clock started to count down. The Rock was in the ring. Who in the “blue hell” would interrupt the Brahama Bull? Chris Jericho, that’s who.
Not only did he interrupt the rock, but he promised the WWE would never be the same again. Jericho immediately made enemies.
He was not one to listen to authority, as William Regal can attest to when a ” certain liquid” was added to his coffee. Jericho quickly became the Intercontinental Champion, European Champion, and a fan favorite.
Stephanie McMahon Debuts
Stephanie McMahon started as the quiet daughter of the Chairman Vince McMahon. She was almost sacrificed by the Undertaker. She was drugged by Triple H and forced to marry him at a drive-thru wedding chapel.
Just another day as part of the McMahon family. Eventually, Stephanie aligned herself with her soon-to-be real-life husband, Triple H. They drove out Vince McMahon and took over the WWE.
The McMahon/Helmsley Regime became bullies. They fired people left and right. She even managed to win the WWF women’s championship. When they turned their attention to Chris Jericho, they met their match.
Chris Jericho clashes with Stephanie McMahon Helmsley and Triple H.
Jericho first became a thorn in Stephanie McMahon Helmsley’s side when he “mistook” her for one of the Godfathers ‘workers.
Remember, this was the 90’s in the Attitude Era. Y2J called Stephanie a “bottom-feeding, trash bag ho. Jericho also cost Triple H the opportunity to become the number 1 contender for the WWE Championship.
This prompted HHH to want Jericho in a match. He demanded that Commissioner Mick Foley make a match with Jericho. However, Jericho was not done humiliating Stephanie.
On SmackDown, Triple H sent Stephanie to the ring to demand an answer to the challenge. Commissioner Foley gave them Jericho, but in a six-man tag. Jericho teamed up with the Dudley Boyz against Triple H, X-Pac, and Roaddogg.
Degeneration X won, but Jericho put HHH through a table. Again, The Game was humiliated. However, Hunter experienced another type of humiliation when Y2J caused him to get a stinkface from Rikishi.
Finally, Commissioner Foley gave HHH what he wanted, a Last Man Standing Match at Fully Loaded. This would be the Ayatollah of Rock’ N Rolla’s greatest champions.
On SmackDown the following week, Jericho took on Kurt Angle with Stephanie McMahon in his corner. She gave Jericho a low blow, allowing Angle to get the Angle Slam and the victory.
Later that night, HHH was defeated by The Brooklyn Brawler because of Jericho. As HHH took his rage out on the Brawler, Y2J stole his limo.
Chris Jericho has since confirmed that there was real heat between him and HHH. Despite the pop they were receiving when Jericho would humiliate the couple was good business.
Next Monday on Raw, HHH told Stephanie to go to the ring and call out Chris Jericho.
” Chris Jericho, I have a proposition for you. Why don’t you come down to this ring, and let’s make up.
I promise you I’ll make it worth your while. I know Chris has said some not-so-nice things about me. I’ve also said and done some things that I’m not very proud of.”
She claimed that when he kissed her, she kind of liked it. Obviously, they were setting Jericho up. She pretty much walked right into her own insultfest.
Jericho appeared on the titantron, telling Mrs. McMahon Helmsley that he felt the same. As Jericho’s music played, DX waited to mug him. Jericho wasn’t born yesterday. He appeared back on the tron and continued to insult Stephanie and The Game.
“Triple H, I know why you are upset, because Y2J got more action in that 10-second kiss than you have in your entire 10-month marriage.”
Triple H was beyond livid. The Game was on. Next week on Raw, Triple H pretended to get into an argument with XPac. This led to a match.
When Jericho came down to interfere, DX ambushed him. Triple H attacked Jericho with a sledgehammer. This was a warning of what the Game is capable of at Fully Loaded.
To make matters worse, Stephanie McMahon Helmsley slapped Jericho. Jericho has gone on record stating that Stephanie McMahon has one of the stiffest slaps.
In her defense, Stephanie said later that, well youre the one who taught me how to make it look real. DX left Jericho a bloody mess. He was sent to the ER as Triple H mocked him.
Thanks to Chris Jericho, WWE Fans would greet Stephanie McMahon Helmsley with a chorus of slurs everywhere she went.
The apple did not fall far from the tree, as Vince McMahon was greeted in the same way most of the time. In the meantime, Triple H became the WWF Champion with the help of DX and the McMahon Family, including his father-in-law, Vince McMahon.
Chris Jericho saw his moment. On April 17, 199,9 Chris Jericho challenged Triple H for the WWF Title. The fans thought he defeated the game when referee Earl Hebner counted to three.
However, it was revealed to be a fast count on The Game. Due to pressure from the McMahon-Helmsley Regime, Hebner reversed the decision. Jerichos’ feud went on with Mr. and Mrs. Helmsley through the summer.
At WWF Fully Loaded, Chris Jericho and Triple H competed in a Last Man Standing Match. Jericho came within several seconds of winning but could not defeat the viscous cerebral assassin.
The war between the two was far from over. Chris Jericho went on to win the WWF Intercontinental title at the Royal Rumble. Unfortunately for Y2J, Triple H defeated him and took the title.
WWF Champion Stone Cold Steve Austin did the unthinkable at WrestleMania XVII and turned heel. He went further, joining forces with Triple H to become the two-man power trip.
The dastardly duo also won the WWF Tag Team Titles from The Brothers of Destruction at Judgement Day. The Two man power trip had all the championships.
At the same ppv, Chris Jericho and Chris Benoit earned a shot at the tag title. The very next night on Raw, Chris Jericho and Chris Benoit defeated The Two-Man Power Trip.
What is even more significant about that night was Triple H’s legit tearing of his quad. This is the infamous injury that put him out for months. It’s also the injury that led to a major return for the Game.

Chris Jericho and Stephanie McMahon-Helmsley – Their Alliance & Rise
In the meantime, Chris Jericho’s star continued to rise. The landscape in the WWE had changed. The world found out that Shane McMahon had purchased WCW a few months ago.
In the summer of 2001, WCW invaded the WWF. Shane McMahon assembled his troops. This included the last WCW champion, Booker T.
In a few weeks, the full invasion plan was revealed, with none other than Stephanie McMahon Helmsley leading ECW and Paul Heyman backing an alliance with WCW.
Vince McMahon’s two children were trying to take over his business. Chris Jericho and Chris Benoit lost the WWF tag team championship to the Dudleys.
At the King of the Ring, Y2J found himself in a Triple Threat for the WWF Title against Champion Stone Cold Steve Austin and Benoit. Unfortunately, he was not successful due to Booker T.
Again, Stephanie McMahon and Chris Jericho’s war of words started.
“Your husband has been gone for such a long time, and I know how lonely you must be to be forced to form a private alliance of your own with three-quarters of the superstars in that locker room, and the lighting crew, and the camera crew, and the sound technicians, and the popcorn vendor in the 15th row.”
Stephanie could not stand Chris Jericho and used the Alliance to take him out. The man she selected was Rhyno, the Man Beast. On SmackDown, Rhyno gored Jericho through the SmackDown set.
If you haven’t seen that footage, I highly recommend checking it out. Chris Jericho was now set for a match against Rhyno at Summerslam with Stephanie in the man beast’s corner. Jericho accepted the challenge in his own unique way.
“At Summerslam, I am going to take care of that smelly, greasy, nasty animal. And I’m going to get you, too, Rhyno.”
At Summerslam 2001, Chris Jericho defeated Rhyno to become the New Champion, despite Stephanie’s constant interference. At one point in the match, he caught the billion-dollar princess and gave her a kiss.
Disgusted, she gagged on the arena floor. However, Jericho was tired of doing things for others. He felt he was relegated to mid-card.
Dissension began between him and other stars, namely the new WCW star The Rock, who defeated Booker T. At Survivor Series, Jericho was part of the WWF team as they exiled the Alliance in a winner-take-all match.
Many believe the whole storyline was just Vince’s final say in the Monday Night Wars. After the defeat, Stephanie, along with the rest of the alliance, was fired.
Chris Jericho’s arrogance began to consume him. He wasn’t worried about pleasing the fans. He wanted the world title.
This led to a feud with The Rock and the WWF Champion, Stone Cold Steve Austin. At Vengeance, Chris Jericho became the first WWF Undisputed Champion, defeating both The Rock and Stone Cold in one night.
His new attitude was not liked by the fans. A month later, Triple H returned to the WWF at Madison Square Garden to a massive ovation.
The Game immediately made his intentions clear: he would enter the Royal Rumble and challenge for the WWF Championship.
Triple H made good on his promise and won the Rumble. Chris Jericho retained the Undisputed title. The two were on a collision, but this time Triple H was a fan favorite.
Business Associates
Stephanie returned to the WWF as well to be with her husband. It was clear the fans respected the Game and hated Stephanie.
To get Triple H over as a face, he threatened to divorce Stephanie. She faked a pregnancy to get him to stay. When Triple H found out, he left Stephanie. Hell hath no fury as a woman scorned.
The former Mrs. Helmsley went to her old nemesis, Chris Jericho. Jericho, now the Undisputed, knew he needed her to defeat The Game at WrestleMania. No one knew the challenger like his ex-wife.
“Stephanie, I used to come to this ring and call you filthy, dirty, and disgusting. You know what, I never met those things. I was just trying to get these people to like me.
What did that ever get me? Nothing. Where did that get me? Nowhere. In reality, I kind of admired you, Steph.
Now that I am the undisputed champion, I see you for exactly who you are. A brilliant, calculating, coniving genius.”
She played right into Jericho’s kiss-up.
“You want the same thing I do. I want HHH to lose. I know his strengths. Most importantly, I know his weaknesses. We are an unstoppable force. I will make sure that you never evvvvvver lose that title.”
It was clear that both were using each other. During HHH’s match that night, he spat at the new business partners as they were sitting at ringside. Stephanie slapped HHH in the face.
The game went to Pedigree, his ex-wife, but was attacked by Y2J. The next night on Raw, Jericho mocked Triple H’s marriage. Stephanie insulted Triple H. This prompted The Game to counter with an insult of his own.
As a matter of fact, it was right out of Jericho’s former playbook. Triple H and Stephanie’s “divorce” reached its peak when Hunter attempted to pedigree his ex.
That’s when Jericho struck HHH with his own sledgehammer in his injured quad. Jericho attacked the Game like a shark. Stephanie looked on, cheering as Jericho reinjured HHH’s leg.
Despite the injury, HHH got revenge on Jericho and Stephanie at Wrestlemania XVIII, becoming the Undisputed WWF Champion. The billion-dollar princesses’ plan did not work, and their business agreement fell apart.
According to Chris Jericho, he had a much more juicy storyline for that match. He suggested that when HHH returned, he was going to say that Stephanie was having an affair.
Jericho said in the vignettes that he was turned around, showing only a ponytail similar to RVD’s. At some point, it would be revealed that she was having an affair with Jericho. However, that was turned down.
Jericho went on to face HHH for the title in Hell in a Cell without Stephanie. He still was not successful. After some time,e Chris Jericho again became Y2J.
The fans accepted him back for a while, that is. Jericho went on to win many more World Heavyweight Championships and WWE Championships.
He had many amazing feuds with the likes of Shawn Michaels, John Cena, and Edge, just to name a few. In July 2002, Stephanie McMahon returned as the General Manager of Smackdown.
As GM, she became a fan favorite, leading the blue brand against Raw GM Eric Bischoff. She was, as the song suggested, “all grown up. She went on to have an I quit match with her own father, Vince McMahon.
Is it 1999 again?
A few years later, Stephanie McMahon returned as the Raw General Manager. As her theme song suggested, she was all grown up. She immediately came face-to-face with her former business associate, Chris Jericho.
Jericho, now a major heel, was a threat to John Cena, who was WWE Champion. Gone was the rock n roll persona. Jericho was now serious in a suit.
Stephanie booked a match with Jericho vs Hacksaw Jim Duggan. Jericho was offended by this and began protesting to the new GM.
Stephanie guaranteed that if Jericho ever refused to do as she said, she would see to it that he never had another match in WWE again.
“Stephanie, I will not compete until the world championship is at stake. I am not going to lower myself. You are a liar, Stephanie, no worse than all these hypocrites.
I am quite ecstatic about your dad coming back because he’s going to give me what I want.
After all, Mr. McMahon knows how much I mean to this show. Next week, nothing you say is going to mean anything. I don’t give a damn what you say.”
Stephanie was now the authority and set Jericho straight
“Raw is my show. My father supports me. Well its not next week its this week. How about you no longer get your opportunity?
How about you no longer get to talk to my father? Maybe you’ll give a damn about this. You’re fired.”
The next week, Mr. McMahon returned. He was more than supportive of his daughter. Jericho immediately interrupted their reunion. Jericho stated that he wanted his job back.
Stephanie suggested that if he really wanted his job back, he would need to apologize. At this time, getting an apology out of Chris Jericho was next to impossible. He apologized to Stephanie, but that was not good enough. The Raw GM made Jericho apologize to the fans.
Jericho got his job back, but left the WWE. He again returned at The Royal Rumble as Y2J. The old swagger was back. The Ayatollah of Rock N Rolla had returned.
Once again, Stephanie McMahon was in charge of Raw, but she was not alone. Triple H was appointed the COO and was now in control alongside his wife. They called themselves the authority.
They claimed they were “best for business. Similar to the McMahon-Helmsley era, no one was safe. The more things change, the more they stay the same, as Y2J interrupted the power couple.
It felt like 1999 as Y2J insulted Stephanie again. Triple H reminded Jericho that it’s not 1999. They were the authority.
Jericho went on to attack a debuting AJ Styles and turn heel again. He then teamed with Kevin Owens, where Ko gave him a taste of his own medicine.
After several grudge matches with his former friend, Y2J again parted ways with the WWE. He went to a rival organization called AEW. There, Jericho continued his legacy, becoming the Painmaker and Le Champion.
There is a strong rumor, though, that Jericho wants to return to the WWE. No doubt a definite in for the WWE Hall of Fame. Chris Jericho has nothing left to prove. He has truly done it all.
Stephanie McMahon ruled as the authority with an iron fist. She even got back into the ring, defeating Brie Bella at Summerslam. She was Triple H’s tag team partner against Kurt Angle and Rhonda Rousey.
After losing to them, she only appeared sporadically. She was announced as the WWE interim CEO after Vince McMahon stepped down temporarily. Behind the scenes, she was the chief brand officer.
She promoted the WWE. Her main job was fighting for the legitimacy of WWE. She has received countless awards and continues to make WWE a brand unto itself.
When Vince McMahon returned, Stephanie resigned. In 2023, it was announced that the TKO had bought the WWE. For the first time in history, a McMahon was not in charge.
Triple H was named in charge of the creative aspect of WWE. This year, Stephanie McMahon will be inducted into the WWE Hall of Fame. How interesting it would be to see Jericho “roast ” Stephanie at the event.
Behind The Scenes
On-screen, they hated each other; their chemistry could not be denied. Backstage, however, was a different story as Chris Jericho and Stephanie McMahon loved working with each other.
Stephanie was recently on Chris Jerichos Podcast. He complimented her by saying she is very much like Vince in the ring. He said Stephanie really honed in on her character, and it’s become a part of her.
He asked her if people get Stephanie McMahon mixed up with her character. She said it does happen. One of the programs she helped launch is WWE’s Be A Star program against bullying.
She points out that she plays a bully on tv. It’s only a character, which is obvious from her approachable demeanor.
She was also responsible for the rise of the women’s division. Stephanie was very instrumental in the #givedivasachance.
The two went over some of their most memorable moments. Jericho told Stephanie he feels like they helped each other get to the next level. Then he said that he said some awful, horrible things to her over the years.
They mentioned the trash, bottom-feeding catchphrase. Stephanie said she was honored that he felt she helped him. She went on to say none of that really hurt her feelings at all. She said it was fun.
“Its a part of what we do. That’s the nature of the business. You build it and build it. Then, finally, give the fans the payoff. I love being the heel.
People want me to be that character. They want me to be an evil, obnoxious Bitch. She said she loves feeding off the crowd and getting booed. “
Jericho mentioned the time in Chicago on Raw where Stephanie had just had a breast enhancement. He told her he remembers several zingers, including calling her the breast…I mean the best, as well as getting the crowd to chant
“Let the b**bies hit the floor.”
It was revealed that Stephanie actually came up with a few of those put-downs. Chris Jericho also mentioned that his work with Stephanie gave them more creative freedom and confidence from Vince McMahon.
He said it’s very interesting to see that Stephanie McMahon is one of the highest executives in the company and is leading it into the future.
The rivalry between Chris Jericho and Stephanie McMahon was a character-driven rivalry. It elevated both stars to a new level.
It also brought Chris Jericho into the WWF Title picture against HHH. It added to Stephanie’s heel persona, allowing her to become more than just in Triple H’s corner.
On screen, they were always at each other’s throats. Behind the scenes, they were always good friends. They were always willing to give back to the business.
Stephanie is, of course, the wife of WWE Head of Creative Paul Levesque, aka Triple H. She is in charge of WWE’s presence as a brand.
She said that her final legacy would be to elevate WWE to the status of a major entertainment company. When TKO took over, she scaled back a bit as her biggest job is being a mom.
This Year, she is being inducted into the WWE Hall of Fame. WWE if you are reading this, how cool would it be for Chris Jericho to roast Stephanie McMahon? It would be another moment that WWE fans will neverrrrr everrrrr forget.






