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Stephanie McMahon was presented as the Billion Dollar Princess ever since she made her WWE debut, and in late 1999, she was already a familiar face among the WWE universe. The fans used to pity her for whatever she went through and how Triple H used to make her life miserable. Things got heated up even more at the Survivor Series event of the mentioned year, where Triple H defended the WWE World title against The Big Show and The Rock.
Vince McMahon interfered during this match and cost Triple H the title. After this event, Triple H kept on making Vince McMahon's life miserable by attacking him again and again, and even his son, Shane McMahon. A No Holds Barred match was announced between the two at Armageddon, where Triple H completely destroyed Vince in front of Stephanie McMahon, Vince's daughter.

Stephanie McMahon remembers her heel turn from 1999
Stehanie kept on begging for her father's life, but Triple H was completely merciless. After Triple H pinned Vince, Stephanie shocked the entire world with an evil smile and by hugging Triple H. It was the first time she turned heel, and he kept on working as a heel until the end of the Attitude Era.
Stephanie McMahon turned heel for the first time at Armageddon 1999
Stephanie McMahon was one of the most hated heels during the time, and the fans even threw abusive words towards her, which was quite common during the Attitude Era. Stephanie recently remembered the time she turned heel for the first time, and she also expressed that getting the hatred was amazing. Speaking on her “What’s Your Story?” podcast, she said the following;

She allied with Triple H after her heel turn
“The things they say sometimes, it’s really funny. My most horrifying [chant] was, ‘she’s got side meat.’ I hate that one, it’s mean. Chicago with ‘she’s a crack w*.’ Most everywhere else, it was ‘s.’ They chanted ‘s*’ as soon as I turned heel, and it was so great.”
“It was at Armageddon which was December of 1999. It was the night that I did the heel turn and got with Paul [Triple H] in storyline, not in reality. The next day, we were in Florida, they came with the ‘s*’ chant and it was the greatest thing I had ever heard cause nobody else got chanted at that way. It’s fantastic! Arenas of people, 1000s of people chanting ‘s*’ at me. It’s the best. That’s the greatest. I mean, who could say that? Not many people.” said The Billion Dollar Princess.