September 1991, a large private yacht cruised towards the Statue of Liberty. It was a clear, breezy evening, and from the upper deck of the Spirit of New York, a golden sunset could be seen glinting off the Manhattan skyline. Downstairs, a party was in flow. Scores of teenage girls in evening dresses and miniskirts, some as young as 14, danced under disco lights. It could have been a high school prom, were it not for the crowd of older men surrounding them. As the evening wore on, some of the men – many old enough to be the girls’ fathers, or even grandfathers – joined them on the dancefloor, pressing themselves against the girls. One balding man in a suit wrapped his arms around two young models, leering into a film camera that was documenting the evening: “Can you get some beautiful women around me, please?” the party aboard the Spirit of New York was one of several events that Donald Trump, then 45, attended with a group of 58 aspiring young models that September. They had travelled from around the world to compete in Elite’s Look of the Year competition, an annual event that had been running since 1983 and was already credited with launching the careers of Cindy Crawford, Helena Christensen and Stephanie Seymour. At stake was a life-changing prize: a $150,000 contract with the world’s then leading modelling agency, Elite Model Management, run by John Casablancas. Trump was closely involved in Casablancas’s competition. In 1991, he was a headline sponsor, throwing open the Plaza, his lavish, chateau-style hotel overlooking Central Park, transforming it into the main venue and accommodating the young models. He was also one of its 10 judges. In 1992, Trump hosted the competition again. On a similarly golden evening in early September that year, another group of contestants boarded the Spirit of New York, chartered for another Elite cruise. One of the girls on the boat was Shawna Lee, then a 14-year-old from a small town outside Toronto. She recalls how the contestants were encouraged to parade downstairs, one by one, and dance for Trump, Casablancas and others. Lee, an introverted teenager who loved to draw but hated school, was in New York for the first time. “A woman at the agency was pushing me,” she recalls. “I said to her, ‘I don’t see why me going down the stairs and dancing in front of those two has anything to do with me becoming a model. And she said, ‘No, you look great, take off your blazer and go and do it.’ So I walked down the stairs. I didn’t dance – I blew a kiss at them, spun around and walked away.” unearthed Video of Donald Trump at Look of the Year Competition - 14 Year Old Girls #trending #viral #2025