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Triple H may be more famous as a heel during his wrestling career, but he emerged as a baby face during his early career after dropping the Hunter Hurst Helmsley character. He was a big part of the DX faction, and after it turned fan favourite in 1998 during its feud with Nation of Domination, he was the biggest part of it since Shawn Michaels was already out with an injury.
He went on to become one of the most famous stars of WWE during the early Attitude Era, but despite his popularity, WWE decided to turn him heel in early 1999. It all started at WrestleMania XV, when he helped Shane McMahon retain his European title against X Pac, who was his DX teammate.

Why Triple H turned heel in 1999
Slowly, he moved away from DX and emerged as a main event star, and he regularly started to challenge for the world championship. One of his early memorable title challenges was at SummerSlam 1999. Triple H recently spoke about his 1999 heel turn while speaking on the “Flagrant” podcast, where he explained why Vince McMahon turned him heel despite immense popularity. He said,
Triple H was one of the top baby face throughout 1998 and early 1999
“So when we get to the end of DX, the run as babyfaces. There’s a moment where I go to Vince and I’m like, ‘I want out of the group.’ And he was like, ‘Why?’ I said, ‘I want to turn heel. Austin is white hot. Rock is on his way up, but he’s going to be a babyface, a white meat baby face.
"Like there’s no — he’s so charismatic There’s no way he doesn’t become that baby face. We need the Darth Vader in this, right? You got two good guys, you need the bad guy. I’m confident enough in myself, I can be that bad guy. But I got to get out of this group and I’ve got to make the shift now.

He won his first WWE Championship on the night after SummerSlam by defeating Mankind
“And the other guys were like, ‘What are you doing. Don’t — ride this into the ground. We’re making a fortune on merch and everything else. Don’t do this, don’t do it. And I was like, ‘But this is not what I want to do.” explained the present WWE Chief Content Officer.
Check out what Shotzi has to say about a potential return here
Triple H won his first WWE World Championship on the RAW after SummerSlam 1999 when he defeated Mankind, who won the title just the night before at SummerSlam. It was the beginning of the ultimate rise of The King of Kings. He remained a heel until 2001, but he missed the invasion angle due to an injury.