A company must hold someone in high regard if they allow them to train the chairman and CEO’s daughter, and in the case of former WWE star Dakota Kai (Charlie), she was presented such an opportunity in 2018. Ahead of WWE WrestleMania 34, Kai was chosen to train recent 2026 WWE Hall of Famer Stephanie McMahon for her match against Ronda Rousey. When Kai was released from the Stamford-based promotion last May, McMahon had nothing but generous remarks to say about the former Damage CTRL Superstar, which still puts a smile on her face today.

“She’s the sweetest person in the world, and always said hello to me. But the fact that she remembers that is insane to me,” the former two-time WWE Women’s and NXT Women’s Tag Team Champion said on “Insight with Chris Van Vliet.” “I was just so grateful to be able to be in the ring with, like, training her, and Ronda, and Kurt [Angle], and Hunter [Triple H], as well. Yeah, she got to DDT me. I was like yes, beat me up, Stephanie…’ And I think that was our first ever meeting. Every time after that, backstage or whatever, she would always make a point to come up to me.”

Unable to beat “The Rowdy One,” McMahon did hold her own at “The Showcase of the Immortals.” As for Kai, she chose not to renew her contract with WWE, leading to her first departure in April of 2022. A few months later, she made her epic comeback with Bayley and  IYO SKY at SummerSlam. Departing again last year, Kai promised her time within the squared circle is far from over, after speculation ran wild that she had retired from pro wrestling.

If you use any of the quotes in this article, please credit “Insight with Chris Van Vliet” with a h/t to Wrestling Inc. for the transcription.