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In November 2014, Emanuel named Bennett as Chicago’s Outstanding Youth of the Year for his activism. Bennett’s work to support Chicago youth includes hosting Open Mike nights for Chicago-area high school students in collaboration with Chicago Public Library, which drew the attendance of fellow Chicago natives and celebrities like Hannibal Buress and Kanye West. In December 2015, Bennett joined with Detroit-based nonprofit group Empowerment Plan to start an initiative called Warmest Winter 2016. The initiative raised money to give 1,000 specially manufactured coats, which doubled as sleeping bags and shoulder bags, and were manufactured by homeless citizens of Detroit, to homeless citizens of Chicago. In June 2016, he hosted the Teens in the Park event, a free youth festival on Chicago’s Northerly Island that drew an attendance of 3,300.