I was watching some old Raws and PPVs from the summer of 1999 recently and it seemed that after winning the King of The Ring that year, Billy was poised to take off to main event status.
After winning the KOR, he started a feud with The Rock, a main-eventer. Smart move. At the time, The Rock was a three-time WWE Champion and his popularity was increasing to Stone Cold Steve Austin levels. I understand why they didn't have Billy actually beat the Rock at Summerslam, but just feuding with him for a month and beating him a few times on Raw was great for Billy's resume.
Win or lose against The Rock, Billy was going in the right direction. He attempted to go after Jeff Jarrett's intercontinental title but thanks to interference from HHH, Billy lost the #1 contender spot to Chyna. Feuding with Jarrett, Chyna and HHH turned Billy into a babyface. As a babyface, it was fair game for him to get a shot at HHH's title. Billy had already feuded with a main-eventer in The Rock, so now he could join the list of other top guys after HHH's title. (Mankind, Stone Cold, Undertaker, Big Show, The Rock, Kane, and The British Bulldog).
But what does Billy do? Reunite with The Road Dogg.
To me, that's what set him back. I like The New Age Outlawz. But this was the time for Billy to make that leap to main event status. Reuniting with The Road Dogg relegated him once again to the tag team division. Sure, The Outlawz feuded numerous times with The Rock and Sock Connection, but this was for tag team gold only. Then The Outlawz returned to DX the next month. By that point, Billy's push was over. He was a tag team specialist in a faction committed to ensuring that HHH maintain his championship.
Triple H turned on DX in March '99 because he had his sights set on the world title. He didn't win it until August that year, but he did what was best for him and not the fans. Billy Gunn seemed to be inspired by this, as he also turned on The Road Dogg and X-Pac, won the King of The Ring, feuded with The Rock, and in September seemed to be poised to make that next leap to the top tier. Instead he got back with Road Dogg. A popular decision, yes. But probably the wrong decision at the wrong time. Just curious to see what would have happened if Gunn had continued his feud with HHH or started a beef with another heel main-eventer like Undertaker or Big Show. The WWE seemed to be prepping him for main event status and I'm wondering what could have been.
Great post! Rejoining Jesse James and DX are definitely among the reasons why Billy never made it. But he did oversell moves a lot and seemed, I dunno, overzealous. Its like he tried a bit too hard to make an impact or come across as charasmatic. He did have charisma and made a big splash in '99 as you stated. Having said that I don't think he could be world champion with that Mr. Ass gimmick. "The One" Billy Gunn and his "love affair" with Chuck were awful gimmicks too. To me Billy was a good entertainer but having questionable gimmicks and being overzealous hurt his chances of ruling the roost.
Billy wasn't a leader. To me he was a better foot solider type. He's like D'lo Brown or Val Venis to me. An exciting mid-carder but not world championship material. Out of everybody in DX only Trips and Shawn Michaels had real leadership skills. Remember when X-Pac had his own stable X-Factor? That was terrible! Not everyone can make it to the main event.
Road Dogg and Billy Gunn came clean about their drug addictions and arrogance in this interview. I knew Road Dogg was an addict but I didn't know Billy was a user, too. I'm posting another interview underneath where the guys really ripped apart Triple H. According to Billy, HHH is the reason Randy Orton never got as big as he should have.
They're both cool with Trips now. That interview when they were dogging him was from years ago. Like all friends they had their ups and downs. Trips was already a competive guy and when he got with the boss' daughter I'm sure he got an even bigger head. That, and the Outlaws being druggies was a recipe for disaster. They're cool now. They were both on the new Triple H documentary "King of kings."
Out of everybody in DX only Trips and Shawn Michaels had real leadership skills. Remember when X-Pac had his own stable X-Factor? That was terrible! Not everyone can make it to the main event.
Road Dogg was a natural born leader too. In fact, I'd say he was the leader of the N.A. Outlawz. But both guys committed the same sin; they remained loyal to that damn Triple H at the prime of their careers. And they knew he couldn't have cared less about them too!
At least Billy followed HHH's lead by turning heel and then winning King of the Ring and doing damn well with a main eventer like The Rock on a week by week basis. Billy was on his way, and if he had not reunited with Road Dogg and remained a heel, he could have been in the 6 Pack Challenge at Unforgiven in '99. Instead that spot went to the British Bulldog, but would have gone better with Billy because he had a long history with both HHH and The Rock.
Billy Gunn and Road Dogg both should have struck while the iron was hot.