These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
To elaborate: during 1999 to 2001, Hunter was an astonishing worker and in-ring talent; his 2000 street fight with Mick Foley at the Royal Rumble has to be seen to be believed. However, he was never the same after his first quad injury. About the same time, Stephanie McMahon became the chief creative authority for WWE...which was also the point that Trips went from simply being an already over-hyped (though talented) wrestler and champion to a physical god who simply could not be defeated under any circumstances by anyone, no matter how talented or capable. Combined with the widespread (and insider-confirmed) rumors about his backstage obsessions with winning at all times, he's come across as as a viciously self-centered individual. The final issue is that he is clearly responsible for the burial of several wrestlers' careers, sometimes defeating credible opponents (like Booker T at WrestleMania XIX) in appallingly one-sided squash matches (he waited a full 23 seconds to make the pin to ram home to the crowd just how inferior a wrestler Booker was). Basically, Trips has actual talent, and he could have been a huge force to elevate others and make wrestling truly great, but he is often just too self-serving to do the industry much good.
He eventually mellowed out some. The next few WrestleManias saw him getting beat by Chris Benoit (via submission), Batista, John Cena (again by submission), and Randy Orton respectively. It'd take him six years to win at WrestleMania again (against Orton). Also, after losing to Batista, Triple H wouldn't win another world title for two and a half years.
Let's play Devil's Advocate. During the first couple of years of his "Reign of Terror", Trips was one of the few stars WWE had who could deliver the goods fairly consistently. This wasn't a great period for WWE in terms of star power: Austin walked out after disagreements about how he was booked, The Rock was making movies half the time, Hulk Hogan's nostalgia run didn't give business the expected boost, and Chris Jericho wasn't getting as over as WWE hoped. When old WCW stars like Scott Steiner and Kevin Nash were brought in, fan response was lukewarm at best, and Triple H definitely did much better than them in terms of in-ring work. Though we can't quite excuse him for all that he was involved in (most notably Katie Vick and the aforementioned Booker T match), he did help the company to stabilize a bit until Benoit, Eddie Guerrero, Orton, Cena, and even Brock Lesnar were ready for bigger pushes.
There's also the rumor that when he was about to win his first World Title at SummerSlam 1999, Stone Cold Steve Austin refused to lose the belt to him. They had to make a 3 way dance with Austin, HHH and Mick Foley, with Foley beating Austin and HHH beating Foley the next night on Raw. Between that and taking the sole punishment for the incident where The Kliq broke kayfabe as Scot tHall and Kevin Nash were leaving, it's understandable why he might want to be in a politically powerful position.
A new factor has come with reports that TV tapings headed by HHH are said to be lessstressful than ones ran under Vince. Taking into account Helmsley's affinity for southern-style angles and concepts (he's pushed for a War Games match for years), and wanting the product to be focused on the workers and not sideshows (he was vocal in his disdain for the Diva Search), many are starting to welcome the idea of Triple H taking over for Vince and being a counter-point for his wife (said to be exactly like Vince). Much to their horror.
Especially against Kevin Dunn, the brains behind the Diva Search and Katie Vick.
Also interestingly enough, Triple H has, in-universe, become the very guy his detractors have accused him of being in real life - although he's yet to crank the self-parody up to Vince McMahon levels.
Creator's Pet: Those who consider him overrated and accuse him of using his influence to bolster his legacy often point to the fact that nearly everyone on WWE TV is sure to eventually mention what an awesome wrestler Triple H is. Whether it's legends and veterans talking about the most special wrestlers of the generation, or his hated rivals constantly praising his in-ring ability, the neverending public praise (both in and out of Kayfabe) for Trips tends to rub some fans the wrong way.
He is married to the HEAD WRITER who is also the BOSS'S DAUGHTER! If that doesn't qualify someone for Creator's Pet, what does?
Well, since he's backstage now and all but assured to be handed (at least partially) the reins to the WWE empire once Vince passes or steps aside, is he more a Creator's Pet or a 'Creator' himself?
Crowning Moment Of Awesome: His 2002 return in Madison Square Garden, which earned him arguably one of the single loudest pops in the history of the industry.
While the pop for his return on 2-21-11 wasn't as loud, he gets bonus points for also interrupting the return of the freaking Undertaker]]
His 2000 run is considered to be the pinnacle of his career.
Either of his major quadricep injuries. You can see the muscle seperate and he insists on finishing out the match. Even led to an interesting moment where one of his opponents (I think Edge?) looks visibly concerned as they try to finish the match. Say what you will about the guy, he plays through the pain.
Dork Age: Triple H's career took a hit during the Katie Vick debacle. Then, in 2003, he kept having mediocre to outright bad feuds with the likes of Goldberg, Kevin Nash, and (most infamously) Scott Steiner. This run, right off the heels of his quad tear and when he was most shamelessly hogging the World Heavyweight Championship for himself, is considered the worst of his career.
Foe Yay: Has it with The Undertaker, most notably, as well as Shawn Michaels when they were feuding from '02-'05 and boatloads of it with Randy Orton in their 2009 feud.
Fridge Brilliance comes in when taking into account that his heel runs has him play a massive dick.
"Funny Aneurysm" Moment / Hilarious in Hindsight, depending on your POV: Triple H and Stephanie McMahon were "married" (and later divorced) in a story line. During this very storyline, Triple H and McMahon actually began dating in real life, meaning Steph stole him from Chyna, and later married and had children. After the "McMahon-Helmsley" storyline, their relationship - on-screen or off - was never mentioned until the "Randy Orton attacks the McMahon family" angle in 2009, which led to the real-life relationship being acknowledged on a few occasions; oddly enough, these moments are usually hilarious.
Of course when DX reunited in 2006 there were several references to the real life relationship, from H musing the guy who got Steph pregnant must have a bazooka to Shawn accusing him of knowing who the father was to mocking the McMahons with a photo of Vince, Shane, and a photoshop of Stephanie's baby: of course it was a terrible job of Triple H.
He began his career as a rich New England blue-blood, Kayfabe of course, now while he's at the height of his career he is a rich New England blue-blood, in Real Life this time. He was born in New Hampshire, is one of the most successful wrestlers ever, and has married into the royalty of Wrestling, the McMahons.
Triple H's comments to CM Punk while the latter was running the Straight Edge Society.
"You don't drink, you don't do drugs, you don't smoke...okay, neither do I, but then again, I don't look like I've been on a week-long crack binge with Amy Winehouse."
Hilarious in Hindsight: When Triple H and Shawn Michaels as D-Generation X parodied Vince and Shane McMahon, Triple H came out wearing a full suit and tie. That was in 2006. In 2011, Triple H is the Kayfabe boss, and suits and ties are exactly what he wears to the ring.
Ho Yay: Hilariously subverts it with Edge and Orton: "You want to do WHAT to my ass?!". Plays it straight and then some with Shawn Michaels.
"I'm Bi- a lot of things, but lingual isn't one of them."
Internet Backdraft: Does Triple H deserve his top billing? How much influence does Stephanie have over his pushes? Is he responsible for the changes in WWE?
Magnificent Bastard: In-character, he took over WWE by marrying the boss's daughter on the night before her wedding to Test, retroactively tried to murder Stone Cold Steve Austin, tried to end his best friend's career, and can always be counted on for whenever the plot calls for Chronic Backstabbing Disorder. In Real Life, he really did marry the boss's daughter and, as part of that and The Kliq, more or less is the most powerful active wrestler in the business, with significant influence over his own storylines. He is also legitimately one of the company's best wrestlers. His two most influential career moments are probably his Face-Heel Turn at WrestleMania XV, which cemented him in this trope, and his brutal match with Mick Foley at Royal Rumble 2000, which was his first great match as champion, a position fans at that time thought he'd cheated his way to in both Kayfabe and in real life.
Memetic Mutation: Triple H would like to inform you that HE. IS. THE GAME! AND HE IS THAT. DAMN. GOOD!!!
He would also like to ask you if you are ready. NO, TV TROPES, HE SAID AAAAAAARE YOOOOU READDDDDDYYYY?!
AH HOO HOO HUH HUH HUH HUH HUH!
LLLLLLLLEEEET'S GET READY TO SUCK IT!
Triple H vs. Broomstick in the Wrestlemania main event!
Narm Charm: Hunter's entrance at Wrestlemania 30 had him come out on stage sitting atop an Iron Throne like chair, surrounded by concubines while wearing a cape and iron cross collar, and a chainmail coif and skull mask that would not look out of place on Shao Khan's head all to the theme of "O Verona". It is so over-the-top and ridiculous, but so fitting for Triple H's character that it still comes off as awesome.
Triple H's tendency to bury younger talents in the days of Evolution was so bad that when Shelton Benjamin & Gregory Helms saw that Benjamin's first match on the Raw roster after his move from SmackDown was against Triple H, Helms reportedly turned to Benjamin & told him how to take the Pedigree, and that was all he needed to know about working with Triple H. Ironically, that was the beginning of the multiple upset victories Shelton got over HHH that legitimized him as a singles star.
Older Than They Think: The "Reign Of Terror" between 2002-2005 is what most fans point to when they talk about Triple H's backstage politics to get out of jobbing but according to Konnan, Triple H had well been doing this since at least 2001. In Triple H's defense, Konnan only brought it up to compare how mild Triple H was compared to what he had to deal with in WCW.
Protection from Editors/Wag the Director: So very much. To elaborate, during the press rounds for SmackDown Vs RAW 2011, a memo was leaked where WWE HQ asked everyone who was covering the game to not use any screenshots in which Triple H was in a vulnerable or losing position.
Rescued from the Scrappy Heap: 2003 was a very bad year for Triple H in terms of fan appeal, although he closed out out with a great title defense against Shawn Michaels on RAW that was PPV quality.. He then kicked off 2004 with a Last Man Standing match against Shawn Michaels at the Royal Rumble that got a standing ovation. Then WrestleMania of that year saw an excellent triple threat match between him, Shawn, and Chris Benoit and an equally awesome rematch at Backlash. This trilogy of matches (as well as his long period of jobbing to Batista the next year) redeemed Triple H in many fans' eyes.
Many members of the IWC who still held a grudge against him for his shovel period, found themselves approving of most of his behind-the-scenes executive decisions and eagerly awaiting the day Triple H takes over the WWE from Vince, thanks to his old-school NWA-style mindset.
Playing a great heel opposite Daniel Bryan leading into WrestleMania XXX, then putting him over like a million bucks on Bryan's way to a memorable title run that night also had a lot of the IWC applauding HHH playing the perfect foil that made the triumph all the sweeter.
Tearjerker: The end of the 10/3/11 RAW, when all of the other superstars,referees,cameramen, and divas walked out on Triple H and he turned and saw one man left, his friend Jim Ross... who promptly got up and left him, leaving him all alone.
Troll: A big part of his recent heel character. From "Aww, did someone not get what they wanted?" on the Raw after the Royal Rumble to saying he should vent his frustrations with angry tweets and then vow to never watch again (along with his friend Mark).
Unfortunate Implications: The WMXIX feud with Booker T, going a very racist route by telling Booker to dance for him, noting his "nappy hair", telling him to fetch him a towel, saying "your kind of people" are simply not champions. In most sane worlds of booking, this would lead to Booker T triumphing over the despicable enemy at 'Mania...only for HHH to beat him (and sending Booker T back down to the midcard), topped with hitting a Pedigree and letting Booker lay there for over a minute before covering him. Apparently, the moral of that story is that "nappy-haired" people like Booker are not champions, indeed.