Triple H is one of the greatest wrestlers in the history of professional wrestling. He made his debut well over twenty years ago yet still wrestles on a part time basis to this day. Plus let's be honest, if he wasn't busy with so many other things then he would probably still be performing in the ring as much as he ever did. Nowadays not only does Triple H still wrestle but he plays a huge part in the day to day running of WWE. He's the COO of the company, is married to Stephanie McMahon who he has three children with, plus continues to prove to his father in law Vince McMahon that he's capable of running the whole company via his work with NXT. The Game truly has a busy but pretty blessed life.
It's not exactly been plain sailing for The Cerebral Assassin throughout his lengthy career though. Triple H has had to battle his way through his fair share of terrible gimmicks and even after marrying Stephanie and becoming a part of the McMahon family there has still been plenty of speed bumps as you'll see during this upcoming list. Nobody is perfect and with an in ring career as long as Triple H's there are going to be some times and some moments that are complete failures. Here are fifteen times that occurrences in Triple H's career weren't exactly a huge success.
15 WrestleMania 2000
Don’t let the photo above of Triple H holding the WWE Championship high over his head fool you. The main event of the sixteenth annual WrestleMania, or WrestleMania 2000 as it was dubbed due to the year it took place, is not recalled fondly by wrestlers or fans for a reason. When you look at the match up on paper that may shock you. Triple H, Big Show, The Rock and Mick Foley all doing battle for the biggest prize in the business, each of whom had their own personal member of the McMahon family in their corner. As you’ll notice going forward in this list, The Game doesn’t often lose at WrestleMania and you’d have to imagine there are some politics involved when it comes to those decisions. On this occasion Vince, who was supposed to be backing Rock, struck The People’s Champ with a steel chair so that Triple H could pick up the win. A poorly thought out angle so that The Cerebral Assassin could stand tall.
14 Wrestling in WCW
Yes that's right, Triple H once spent some time wrestling for WCW. A Superstar who seemingly has WWE blood coursing through his veins once performed for the enemy, during the mid 1990s at the height of the two companies going to war no less. It was before The Game had ever set foot in WWE and he wasn't exactly given much to work with. He began his time there as Terra Ryzing. During an interview Triple H said they simply wanted to call him Terrorizing and when he said he thought he should have a first and last name, that's what they came back with. A little while later WCW decided to play on his real name, Paul Levesque, and Triple H had to speak with a french accent. Needless to say it wasn't long after that The Game headed to WWE.
13 The Connecticut Blueblood
Hold your horses though! It wasn't all plain sailing for Triple H once he made that jump from WCW to WWE. By no means did he walk through the curtain of Madison Square Garden on his first night with the company, sledgehammer in hand and start winning World Championships. No, in fact when he did first set foot in WWE all the way back in 1995 his first gimmick wasn't exactly that different to the one he had been portraying in WCW. Luckily The Game could now drop the French accent but he would continue the façade of being higher class as Hunter Hearst Helmsley, The Connecticut Blueblood. The man who would later become a Cerebral Assassin didn't exactly have a memorable time while playing this character, participating in a hog pen match and losing in extremely short order to Ultimate Warrior at WrestleMania XII.
12 King Of The Ring '96
No we have not made a mistake, and no your eyes are not deceiving you. Triple H is in fact not in the photo you can see above. The point of this entry is that he should have been. Stone Cold famously won the 1996 King of the Ring tournament and the image above is him giving his victory speech and Austin 3:16 officially beginning. The thing is Triple H was the man originally pigeon holed for that tournament win. Shortly before the event the infamous curtain call happened when Triple H and the rest of The Kliq broke Kayfabe so they could publicly say their goodbyes in the ring. Somebody had to pay for that, and that somebody was Triple H. The Game's launching pad was taken from him and it took a while for him to get his career back on track.
11 WrestleMania with Randy Orton
On to another WrestleMania flop for Triple H, his show closer with Randy Orton at WrestleMania XXV. Unfortunately for the two men involved, considering they now have 27 World Championships between them, it'll widely be regarded as one of the most forgettable WrestleMania main events in the event's history. In all fairness to The Game and The Viper it wasn't completely on them. Earlier on in the night The Undertaker and Shawn Michaels had staged the first of their back to back WrestleMania epics and this one is the one that's considered by many in the business to be the greatest match of all time. Even the likes of Orton and Triple H had a very hard time following that.
10 Three Strikes At The Streak
The Undertaker may have since lost twice at WrestleMania, but take nothing away from him he will always hold the greatest streak in the history of professional wrestling, his 21 straight wins at The Show of Shows. Three of those 21 wins were actually against Triple H, the final one coming at WrestleMania XXVIII. The two did battle inside Hell in a Cell with Shawn Michaels acting as special guest referee. It involved a spot where HBK super kicked The Deadman straight into a Pedigree and I remember watching live and thinking it would have been the perfect way to end The Streak. It's even rumored that The Undertaker wanted Triple H to end The Streak that night but The Game flat out refused. In hindsight maybe it would have been the perfect time to do it and Triple H should have taken The Phenom up on the offer, if the offer was indeed there.
9 Mocking The Nation Of Domination
WWE is no stranger to playing through some angles that are in extremely poor taste, in fact this particularly offensive one isn't even the highest ranking in this list. Back during the Attitude Era WWE offending people was something the company would do on a weekly basis, you could even argue that they thought it drew ratings. Well on an edition of Raw during the late '90s Triple H and his DX cronies decided to dress up and mock their rivals, The Nation of Domination. Not too bad right? Well it gets a lot worse when you discover that most of The Nation's members were black, so DX thought it would be okay to in turn paint themselves black in order to mock their rivals even further. It really doesn't feel like something that should have flown on TV only 20 years ago, and something Triple H would likely want to forget.
8 Heat With Goldberg
Despite his tremendous fame, popularity and success in WCW, Goldberg's short first run in WWE was not exactly a memorable one. The bulk of his twelve months with WWE between 2003 and 2004 involved a heated rivalry with Triple H. Rumor has it that said heat wasn't reserved to the ring however and that The WCW Icon and The Game were not each other's biggest fans outside of the ring either. Think of that what you will, but it certainly makes sense when you think of the sway Triple H would have had in the company at that time compared to Goldberg. The Cerebral Assassin had to defend his World Heavyweight Championship in an Elimination Chamber involving Goldberg, and despite Bill running through everyone else in the match Triple H and his sledgehammer abruptly stopped him winning the gold, pumping the brakes on Goldberg's WWE run in the process.
7 WrestleMania With Sting
While we're on the topic of Triple H using backstage politics to get the upper hand on former WCW talent, let's move swiftly on to his WrestleMania 31 match up against The Icon, Sting. I vividly remember going into this edition of The Showcase of the Immortals honestly thinking that this was the only match that I could 100% predict, and that Sting was unquestionably going to win. It was his first match in WWE and it seemed crazy to have him lose. Of course if I had thought with my head rather than my heart and done my research I would have known that of course Triple H was going to win. We the fans had waited years and years to see Sting in WWE, truly believing that the time had passed. I'm sure Sting is simply happy that he got to have a WrestleMania moment, as am I in all honesty, but I still think it would have made so much more sense for him to defeat Triple H.
6 Rivalry With Scott Steiner
There are a handful of top Superstars who can put on a great match no matter who they're in the ring with. AJ Styles has that deserved reputation, as did Shawn Michaels when he was at his best. Triple H may like to think that he can also brand himself with that hard earned and rare mark but there is too much evidence pointing to the contrary. Maybe the most evident example of that is when he was trusted to feud with Scott Steiner on his return to the company in 2002. It did not go well. Steiner said some derogatory comments backstage after working with The Game and clearly that only made a bad situation worse. WWE thought they had finally got a big name from the then defunct WCW but alas, Triple H couldn't get the best out of him.
5 Heat With CM Punk
CM Punk's exit from WWE is probably the most infamous in recent history. It's no secret that Punk butted heads with higher ups back stage time and time again and in his tell all podcast following his departure, Punk made no bones about not seeing eye to eye with Triple H. While others could see Punk's worth and how much the fans loved him, unfortunately the two people that mattered, Vince McMahon and The Game, did not. Even though Punk was WWE Champion for well over a year at one point, it was made abundantly clear that even though he was champ they didn't want him in the main event. When it came to big names, Punk didn't win. He had to lose matches that he arguably should have won to The Rock, Brock Lesnar and yes you guessed it, Triple H.
4 WrestleMania With Roman Reigns
On to yet another failed WrestleMania moment for Triple H, his build and eventual match with Roman Reigns at WrestleMania 32. Clearly Triple H convinced someone backstage that him versus Roman closing WrestleMania would be a great idea despite all the flack Reigns was already getting. Surprise surprise, it flopped. Every year The Show of Shows seems to get longer, so ending what felt like a ten hour epic with a match no one really had any interest in was never going to do well. The plan clearly was to make Roman into some sort of hero after Triple H and Vince McMahon had stacked the odds against him and managed to prise the WWE Championship from him. Swing and a miss and you would think WWE would have realized by now that The Game inserting himself into WrestleMania main events doesn't normally go down well.
3 The Return Of Evolution
WWE has been involved in some pretty incredible and dare I say legendary factions. His time as a part of D-Generation X saw him rise to prominence then during the 2000s he felt the need to create his own, fresh stable. So came Evolution. The first run of the famous group was extremely successful and launched the careers of both Randy Orton and Batista. Then years later, when Batista returned to WWE, Triple H thought he'd get the old band back together. Big mistake. Attempting to recreate the magic once brought about by Evolution simply did not work and actually resulted in Batista once again leaving WWE with a bad taste in his mouth. They had some good matches with The Shield but that was about it.
2 WrestleMania With Booker T
There have been plenty of Triple H's failed WrestleMania appearances on this list, but this one takes the cake. At WrestleMania XIX Triple H did battle with Booker T, and The Game won the match. The match itself is not the issue here, it's what was said in the build to it. On an episode of Raw during WrestleMania season that year The Cerebral Assassin cut a promo on his upcoming opponent, citing that 'people like him' don't get to reach the level he was at. Considering the severe lack of black World Champions in WWE's history, even up until the present day, the comments were understandably viewed as being pretty racist ones. You'd have thought that on the back of the controversy Booker would have won the belt but alas as I previously mentioned, that was not the case.
1 Katie Vick
This one is and will forever be regarded as the lowest point of Triple H's career. During the early 2000s The Game was embroiled in a rivalry with The Big Red Machine, Kane. During said rivalry Triple H made some heinous accusations about his opponent, namely that he was responsible for the death of a woman named Katie Vick and then as if that wasn't bad enough, that he had sex with her following her death. The Game went as far as to don a Kane mask and clamber on into a coffin so that he could simulate the whole thing. Yes this really happened on WWE television and it was really Triple H instigating it all, with Vince McMahon working the strings no doubt. Safe to say we won't be seeing any more necrophilia based angles any time soon.