 In 1989 he began working as curator of European Painting and Sculpture at the Kimbell Art Museum and he was appointed to senior curator there in 1990.In 1995 Bailey began working as chief curator of the National Gallery of Canada, Ottawa, and was appointed Deputy Director and Chief Curator in 1998.In 2000 he became the Chief Curator of The Frick Collection where he would later be promoted to Deputy Director and Peter Jay Sharp Chief Curator.