Photos from 2012 show 66-year-old Trump chatting with 20-year-old Olivia Culpo, while 17-year-old Kendall Jenner makes her first runway appearance. At the fashion show held at Trump Tower on September 7, 2012, Culpo, who was crowned Miss USA, and former owner of the competition, Trump, were sitting in the front row. Jenner walked for Sherri Hill as part of Mercedes-Benz Fashion Week. While Trump wore a suit, Culpo wore a conservative dress and the Miss USA sash. In one photo, Trump can be seen whispering something in Culpo's ear. Turbulent Relationship This fashion show was one of the recent occasions where Trump had a positive view of Jenner. Jenner later openly expressed her thoughts about the former president. In 2018, Jenner participated in a protest wearing an anti-Trump jacket. The jacket had the words "God save us... he's not my president" written on it. In the same year, during a TV program, when asked "Who wouldn't you want to come to a crazy party?" she answered "Donald Trump," making everyone laugh. Jenner also made social media posts criticizing Trump's border policies.
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