Silverstein, a real estate developer and philanthropist, has an extensive record of leadership both within and beyond Chicago's Jewish community. He chaired the Jewish United Fund/Federation Board from 2014 to 2016, the JUF Annual Campaign in 2011. Silverstein is a Trustee of the Museum of Contemporary Art and a Board Member of the Ann & Robert H. Lurie Children's Hospital. He also has long served on the board of Solomon Schechter Day School, which both he and his children attended. Silverstein and his wife, Karyn, live in Highland Park with their three children.