Hilary Clinton recently took on a legal knowledge quiz against the one-and-only Kim Kardashian and lost. In Hillary and Chelsea Clinton’s new documentary series Gutsy, the former secretary of state who was previously a practicing lawyer and law firm partner went on head to head in contest with Kim Kardashian who is also a law student.

Hilary admitted in the episode preview, “I think Kim has an unfair advantage,” per People when Chealsea aka the quizmaster reasoned, “Kim has studied more recently than you.” Following a rigorous run of questions about deadly force, variability between extortion and robbery and more, Kim wins with a big majority of 11-4 against the political figure. Talking about the loss, Clinton revealed her thoughts on the quiz to the outlet, “Oh, it was heartbreaking!”

As for Kardashian, she opened up about giving the baby bar in the episode and shared, “My kids were there every time I opened my results, and so they’d see me cry. And the last time, they saw me cry the best tears of happiness that I did it.” Clinton praised the KKW founder for her hard work afterwards, “She worked so hard (on the bar) and persevered.”

Chelsea then talked about supporting Kardashian’s cause of working for prison reform, “She’s very self-aware that her celebrity can make a difference positively, and where it may make a negative difference. She never wants to make a negative difference, so being judicious and thoughtful about when and where and how she engages was really impressive to us. I want, even beyond this series, to do whatever I can to help her in that work.”

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