“You must roll your hoop,” said Class Dean John O’Keefe at the starting line of the 119th annual Hooprolling on May 3. “It’s not called the race where I wear my hoop around my waist and Hula-Hoop my way.” But a Hula-Hoop played a role in this year’s victory after all—winner Alex Poon ’14 may have had a bit of a competitive advantage because of the toy. His mom, Helen Mar Poon ’82, won Hooprolling her senior year and started training her kids in the intricacies of the skill with a Hula-Hoop almost as soon as they could stand up. (Alex’s sister, Cathy, came in second in 2011.) Alex is the first transgender student to win the traditional event. Biologically female, he identifies as a straight man. Poon is from McLean, Va., and majored in computer science. He rolled the Poon family hoop, which has been passed down to each member who has attended the College and is emblazoned with their names. “There are blue stars around my mom’s name for winning,” Poon told the Wellesley News. “I’m looking forward to adding blue stars around mine.”