Triple H’s Favorite Moments in the 25-Year History of Raw

Ahead of Raw’s 25th anniversary show, WWE’s Paul “Triple H” Levesque gives us his most memorable moments in the show’s history.

In its 25 years on air, WWE’s Monday Night Raw has come to be defined by its moments even more than its wrestling. As far back as Gorilla Monsoon throwing Bobby “The Brain” Heenan out of the building in 1993, Shawn Michaels’s collapse against Owen Hart in ‘95, or Brian Pillman pulling a gun a year later, Raw—an industry innovation as a live, weekly show—sought an element of unpredictability, even before the Attitude Era made outlandish hijinx standard operating procedure.

Before the show’s 25th anniversary episode airs this Monday at 8 p.m. Eastern on USA Network, SI spoke with WWE executive vice president Paul Levesque, better known as Triple H, to discuss his favorite moments from the show. “To me the ones that stand out are the ones that seem to make a difference in the company as a whole, that shift the landscape,” says Levesque, who debuted on Raw in 1995. Below are Levesque’s favorites, which range from the landscape-shifting to the personally significant.

1. Stone Cold Steve Austin confronts Mike Tyson (January 19, 1998)

“Mike Tyson was probably—positively or negatively—the most recognizable face on the planet: the ‘baddest man on the planet.’ And you had our new resident baddest man on the planet, Stone Cold Steve Austin, whom fans were just gravitating to in a way they’d never done before, walking out and flipping off Mike Tyson. That was the shove heard ’round the world. It just lit up a whole different feeling about WWE and the company in general. That was the start of a moment in time where everyone started talking about what we were doing.”

2. D-Generation X invades WCW Monday Nitro (April 27, 1998)

“No one talked about the other wrestling promotions at all, let alone got in a tank, drove over to their front door and tried to get in the building. It was unheard of. Even when we were doing it, it was surreal in that moment. Billy and Road Dogg and X-Pac—when they came to TV that day, they had no idea. There was only maybe four of us that did: Vince, a couple other people, and myself. As they walked down the hallway they walked up to me and they were like, ‘I think we just saw a bunch of army stuff with our logos on it? And there’s a tank outside? What are we doing?’ I was like, ‘Oh my god, I can’t tell you right now, but trust me, it’s mind-blowing.’ When I finally told them, they were like, ‘We are not doing that.’

“The mistake was not trying to get in the building right away. We did a bunch of other stuff so by the time we tried to get in they knew we were there. But I would’ve liked to have gotten in the building and see what they did.

“We were gonna go to the ring, cut a promo, just be us. The idea was to try to get in. We even had an escape plan. We had a crew with us, so we had multiple cameras. A couple were dummies, a couple were real. We had dummy people with dummy tapes, so that if it went down, we could grab the tape and create confusion of multiple tapes and multiple cameras and everybody could just try to get out of there.

“We come back and everybody is buzzing. They were on the air before us and we clearly went and had done this earlier in the day and brought the tape back to put on the air. The question was, what if they come here? What if they all get in cars and they send them over here? And everybody was freaking out. I remember thinking, that’s a good point, what if they do come over here? Vince walks over and somebody says to Vince, ‘Here’s the concern: what if they send a crew over here and pull up to the door?’ And Vince looks at everybody and goes, ‘Open the door and let ‘em in. What show are you gonna watch: the one with nobody on it, or the one with everybody on it?’ I thought, This is why we’re gonna win.”

3. Triple H returns from injury at Madison Square Garden (January 7, 2002)

“This is a personal one for me. I tore my quad on Monday Night Raw on live TV [in 2001], an injury that I was told later by Dr. James Andrews, ‘You’ll probably never wrestle again.’ Then to come back in 2002 at Madison Square Garden, sold out—I will never be able to get that feeling out of my brain. It’s locked in there. You have every fear and every doubt in your mind about, ‘Oh, what if they don’t remember? What if they don’t care?’ Then you get the reaction, and for it to be at Madison Square Garden, Monday Night Raw, live—it just couldn’t have been any better.”

4. Triple H’s secret wedding to Stephanie McMahon (November 29, 1999)

“This is a personal one but I also think it’s a big shift as that Attitude Era continued forward. Steph was a new character—Vince’s daughter comes in and she’s gonna marry this wrestler and the whole world is watching and out comes the evil Triple H and we’re already married. It started this new McMahon-Helmsley Era and then Vince disappeared—it put a fresh coat of paint on a whole lot of things in one fell swoop. It was kind of the launch of Stephanie McMahon as a character. Now ironically she’s my actual wife—that’s why it worked so well. We always say we had a dry run on TV first.

“We had no idea [the storyline] would last past a couple of weeks. There was a storyline concocted for her to get to this wedding [with Test] on TV. Everyone loves a wedding on TV. The guy who was writing it left us and there was no plan in place as to where they were gonna go. This wedding was coming up in a couple of weeks and talking to Vince about it, there was zero plan. In fact, they so didn’t know what they were gonna do with it that if you look back in time there was a moment shortly before that where they had to do a thing where Steph got hit in the head with a garbage can and couldn’t remember who she was, so they had to postpone the wedding because she was injured. The reason that was done is because they didn’t know what to do with it. It was like, ‘We’re gonna have this stupid gigantic wedding on TV and what’s the big finish?’ There was none.

“So Vince and I had a storyline going with each other where we hated each other. He had banned me from ever getting a title shot and I said, ‘Look, the worst possible thing I could do would be for me to marry your daughter. What if something happened and I ruined your whole thing and we say at the pay-per-view, at Armageddon, if you win I annul the wedding, if I win I get a title shot.’ That was the whole storyline.

“The next day, when we did the whole thing where Steph went on TV the reaction to her was so unbelievably off the charts that I remember being at Gorilla position right before we walked through the curtain with Vince and him just looking at me and going like, ‘Oh, I smell money, this is huge.’ We had no idea. We thought we’d get a reaction but I don’t know that we thought it would be anything like that. Once she got that reaction, Vince was like, ‘We’re gonna turn her and she’s gonna go with you and I’m gonna disappear and you guys are gonna run roughshod.’ He just took it and ran with it. It became this epic storyline. But that wasn’t the intent up front. At that point in time I had probably spoken 10 whole words to Stephanie. I didn’t know her from a hole in the wall. It was just a storyline where it gets us out of this wedding, gets me and Vince to this match, cool, that’s an out, good out! It was just one of those things that we dug the shovel in and there was gold in there.”

5. Stephanie McMahon announces the first women’s Royal Rumble (December 18, 2017)

“Watching Steph stand in the ring, not as a character, as legitimately the Chief Brand Officer of the company and announcing what, if you went back 20 years, would have been unthinkable—30 women in a Royal Rumble match with the same rules as the guys, where the women are having the quality and the kind of matches on a regular basis that rival the guys and the equality that comes with that. That was almost unthinkable. The times had changed and things had moved forward. I feel like when we did the wedding thing and Steph became this huge, controlling character in the show, it was this moment of, ‘Wow, hey, there’s a WWE show where the woman is the power broker.’ That was a different take on everything. Then to see that go full circle where it’s changed the entire landscape of what it is, and just for me personally to see her, that was a huge moment. That was another shift in the entire landscape of WWE.

“I think it’s something we had been building to for a while in my mind. It started four or five years ago when we started training the women differently at the Performance Center. We started giving them different opportunities through the Performance Center and NXT and that kind of morphing its way up and people accepting it—and not only accepting it, but demanding it with #GiveDivasAChance. Even when we did the Mae Young Classic, looking at that and saying, ‘Oh, it’s probably gonna be 16 women,’ and then realizing, ‘No, we can do this with 32.’ We can full-blown do this. There’s enough talent boiling up now that we can make this happen in a big way. Then that starts to spark, ‘Hey we have enough women, we can make a Rumble happen.’ They’ve had Hell in a Cell matches.

“You know, it completely changed that landscape. I look back in time and from a character standpoint there was, in that timeframe, a paradigm shift. It was happening with Chyna with DX. Women all of a sudden were in a different place and those moments started to bring together more. What’s cool about that is those two moments kind of go full circle to now.”