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Just to make things clear, I do like Triple H and I do consider him one of the best of all time. Today he is a fantastic and ruthless businessman who will surely take WWE to new heights when and if Vince McMahon ever steps down.
However, we all know he used his ego and backstage politics to climb through the ranks rather quickly and then put things favorably in his direction going forward. Some of the times it wasn't a bad decision, but others he just let his ego control things and that brings me to these top ten pay-per-view matches Triple H should have lost.
#10 Triple H vs Carlito- Unforgiven 2007
Carlito was always a star in the making. Defeating John Cena for the WWE United States Championship in his debut match, and winning the Intercontinental Championship during his first appearance on RAW. WWE certainly seemed to have big things planned for the son of Carlos Colón. It just never really panned out though, and this loss contributed to why.
After he had suffered a legitimate torn right quadriceps in early 2007, Triple H returned at SummerSlam 2007 and quickly ran through Booker T in 8 minutes.
He would then reignite his feud with Vince McMahon, with McMahon selecting Carlito to face 'The Game' at Unforgiven. This was Carlito's big chance to be a player, the match was even announced as a No Disqualification match where the NO DQ rule only applied to Carlito, this surely meant the seemingly new top heel would score the win and set up bigger things to come, right?
Not really. The match was okay overall but Triple H gave him nothing and pinned him in just under 11 minutes. As far as being a top guy was concerned, Carlito never recovered from this loss.
#9 Triple H vs Kurt Angle- Unforgiven 2000
This was possibly the best feud of the year 2000, largely due to how unexpectedly good it was. Triple H and Kurt Angle worked so well together that they would also feud in 2001, 2002 and now, 18 years later, in 2018.
Kurt Angle was WWE's hottest new star after his late 1999 debut, so they needed to be careful about what wins and losses he needed to take. Things were a little rocky for Kurt for a while after taking in quick squash pay-per-view losses to the Big Show and The Undertaker, but it seemed like this love-triangle feud would be where it turned around. The Angle/Triple H/Stephanie romance would provide many entertaining segments between August and October, which would all seemingly lead to a Kurt Angle PPV win, but that didn't happen.
Allegedly the plan was for Stephanie to turn on Triple H at Unforgiven 2000 and help Kurt score the win but plans changed for whatever reason and instead she would cost Kurt the big one, giving him a 4th big loss to a top star on a PPV within the past few months. This would have halted the career of any other star but fortunately, Kurt would bounce back the following month and lift his first WWE Championship from The Rock at No Mercy.
#8 Triple H vs Umaga- Cyber Sunday 2007
Umaga was one of WWE's hottest rising stars of 2007. After winning all of his one-on-one matches in 2006, mostly squash matches, 2007 was when Umaga was allowed to shine in competitive matches. His status on the card had been up and down all year, from feuding with John Cena for the WWE Championship to the Battle of the Billionaires to Santino Marella.
After Carlito was almost squashed by Triple H, Vince McMahon next selected Umaga to battle The Game. He fared off better than Carlito, in at least one match, but his losses were even bigger, mainly because Umaga and Triple H would collide on 3 pay-per-views in a row, and Umaga wouldn't take in a single victory. Their first match was a joke. Although a WWE Championship match, Triple H pinned Umaga in less than 7 minutes at No Mercy. Next, in what should have been the Umaga victory, Triple H pinned him in a very exciting Street Fight at Cyber Sunday. Finally, In a 4 on 5 Survivor Series Elimination match, the 4 members of team Triple H easily beat the 5 members of team Umaga.
Much like Carlito, Umaga wouldn't get close to the main event status again.
#7 Triple H vs Jeff Hardy- No Mercy & Cyber Sunday 2008
WWE officials saw everything in Jeff Hardy, during the Hardy Boyz run, during their 2002 split, and 2006-2008 reunion. The WWE Championship was surely in his future, and it was, just not exactly yet.
This entry comes in as two for one. Following a suspension in early 2008, this was Jeff Hardy's chance of finally climbing back up the ladder. The most popular star on Smackdown and probably all of WWE, Jeff Hardy entered No Mercy on a wave of momentum, which included a pinfall win over The Undertaker a few weeks earlier. Hardy and Triple H had a solid match at No Mercy but 'The Game' would pin him after a pedigree. Hardy would challenge him again a few weeks later at Cyber Sunday, this time receiving almost all votes in a poll to challenge him, but would again go down to the pedigree.
Due to his popularity, WWE should have given Hardy a win at least once as he would eventually win the Championship at Armageddon that December, for an uneventful four-week reign. He could have really used those extra two months as Champion.
#6 Triple H vs CM Punk- Night of Champions 2011
CM Punk literally brought many fans back into the WWE product in 2011 thanks to his stirring shoot promo on the company on RAW that June. In what was dubbed 'The Summer of Punk', he gave a dozen eyebrow-raising worked-shoots in the following two months, and would defeat John Cena for the WWE Championship in an excellent match at Money in The Bank, and a damn fine re-match at SummerSlam. Things slowed down then, he dumped the WWE Championship to Alberto Del Rio and entered a feud with Kevin Nash and Triple H.
The mini-feud with Nash was thankfully quietly ended and Punk battled Triple H in place. After at least one unscripted shoot where Punk easily got the better of Triple H, 'The Game' was ready to stop what was left of Punk's momentum train. Although the match between them at Night of Champions was a thrilling one, Triple H's win was not needed. Thankfully Punk bounced back 2 months later to win the WWE Championship that he would hold for over a year. Punk and Triple H would never face off again but were planned for a match at WrestleMania 30 just before Punk quit WWE. Could he have defeated Triple H? Just maybe.
#5 Triple H vs Randy Orton- Unforgiven 2004
Randy Orton was WWE's hand-picked face of the company as early as 2003. He was given a major boost as a member of Triple H's Evolution stable and was one of the best performers on RAW throughout 2003 and 2004. Then the plan came to have him shoot up the ladder on his own, and things got a little messy. Orton captured the World Title at SummerSlam 2004, much earlier than planned. Allegedly the plan was for Orton to win the 2005 Royal Rumble and basically be the Batista of that Triple H vs Batista feud. However, Orton was getting more popular every week, which likely contributed to the alleged change of plans.
In a memorable segment, Evolution turned on Orton on the post-SummerSlam RAW and began his face run, and it would almost immediately go crashing down. Triple H would surprisingly defeat Randy for the World Championship at Unforgiven, ending the Legend Killer's reign at just 28 days. The loss killed almost all of Orton's momentum instantly. Fans just seemed to have lost interest after this and Orton would lose to Triple H two more times on pay-per-view before his planned redemption at WrestleMania 21.
It would be 3 years later before Orton would be a World Champion in WWE again, this time trading victories with Triple H in several Championships pay-per-views over the next 2 years.
#4 Triple H vs Chris Jericho- Fully Loaded 2000
A mini-feud with Triple H in 2000 helped Chris Jericho rise up the WWE card, for a little while at least.
Chris Jericho would surprisingly upset Triple H in a WWF Championship match on the April 17 episode of RAW. Referee Earl Hebner made a fast count when Jericho pinned Triple H, causing Jericho to win the title, but later reversed the decision due to pressure from Triple H, and WWE does not recognize Jericho's reign as Champion. The feud ended just after but helped Jericho maintain a good position on TV. The two would have an official feud in July, which resulted in a Last Man Standing match at Fully Loaded.
This was easily one of the best matches of the year and Jericho looked like a star. However, Triple H would pick up the win, despite Jericho being planned to originally, and Jericho would then shift down the card back to Intercontinental Championship pursuit for another year. Jericho gave one of the best performances of his career here, defiantly the best up until that point, so it is a shame Triple H didn't see anything more in him at the time.
#3 Triple H vs Rob Van Dam- Unforgiven 2002
Think of the popularity that Daniel Bryan had in late 2013. Rob Van Dam was actually in a similar situation in 2001, only it is not as well remembered as this was when the like of The Rock and Stone Cold Steve Austin were full-time, so popularity like Van Dam's could easily have been set aside, which it was. RVD was so popular, that he actually entered WWE as a heel, but was so popular, he even ended up winning the PWI Award for Most Popular Superstar of The Year.
RVD was climbing the ladder for most of 2002. Having several Intercontinental Championship reigns during the year, he picked up big victories over the like of Eddie Guerrero and Brock Lesnar. RVD would pin Triple H in a tag team match on RAW, leading to him winning a number one contenders match the following week. For those 2 weeks, Van Dam was presented as a legit challenger but went down shortly after. On the go-home edition of RAW for Unforgiven, Triple H cost Rob the Intercontinental Title and gave him a post-match beating. This made it seem like Rob would be coming out on top the following Sunday, but instead, Ric Flair swerved turned on him, costing him the match and title. The match itself was decent but it came off like Triple H wasn't giving RVD much effort.
RVD didn't recover as a main event player until he would actually win the WWE Championship in 2006.
#2 Triple H vs Sting- WrestleMania 31
It happened! It finally happened! After 13 years of the closing of WCW, the Icon Sting finally joined WWE. We would finally get to see the dream match of he and The Undertaker, and possibly more!.... Well actually no.
Instead Sting debuted costing Team Authority at Survivor Series 2014, obviously leading to a match between he and Triple H. We didn't really know where this would lead to after WrestleMania but the popular opinion was Sting would defeat Triple H in what was to be his first ever WWE match and then stick around for a while, possibly in a different role. Instead the night of WrestleMania 31, the feud took more of WWE vs. WCW tone when DX and the NWO got involved, and as awesome of a moment, as that was, it soon became clear that Sting was no longer the favorite. Triple H pinned him and that was that. In what Sting thought might have been his only WWE match, he lost to Triple H to feed his ego.
What a waste.
#1 Triple H vs. Booker T - WrestleMania XIX
I don't think Triple H thinks very highly of Booker T. After one year of the mid-card, former 5-time WCW Champion Booker T was finally getting the big push. The build-up to his match with Triple H for the World Heavyweight Championship at WrestleMania, complete with racism, making Booker's WCW career look like a joke and bringing up his young criminal record, was designed to give Booker T the WrestleMania moment he deserved. This was, in fact, true, Booker T was planned to beat Triple H for the World title, but The Game had different plans.
Just like with Rob Van Dam at Unforgiven 2002, WWE was ready to pull the trigger with one of the most popular stars in the company, but same as Rob, Triple H didn't see that in Booker T, so he pulled his creative control card. The match itself was decent, but it's ending was designed to make Triple H look like the best in all of WWE. Where it took The Rock three Rock Bottoms to defeat Steve Austin, Brock Lesnar three F-5's to defeat Kurt Angle and Hulk Hogan 3 Atomic Leg Drops to pin Vince McMahon, Triple H hot Booker T with one pedigree, then laid in the ring for a full 19 seconds, before pinning him. Booker T wouldn't see the main event scene again until late 2004 and wouldn't be a World Champion in WWE until 2006.
The next time Triple H faced Booker T on pay-per-view was when he returned from his torn right quadriceps at SummerSlam 2007. Triple H squashed him in 8 minutes. The Game gave him nothing to work with.
What makes Sting special? His first AEW opponent opens up RIGHT HERE.
