The case traces the path followed by Theaster Gates, an independent philanthropist and artist, to transform the South Side, Chicago. Gates pursued the “creative placemaking” to develop the neighborhood that was mainly comprised of African American. The leading cause of Gates’ increasing efforts was the powerful belief in the life-changing power of art and a personal responsibility to revitalize his neighborhood where he wants to stay and live even when he can afford to leave. Gates’ belief on the artists’ power of highly creative and could change the entire world, becomes trustworthy because of his competency to straddle different worlds. The case asks students to evaluate and discuss the future approach for Gates and what could be the effective strategies that could lead his efforts and organizations towards expansion.