More surprising, and more likely to make waves in the art world, is the choice of Sherald to paint Mrs. Obama’s portrait. Sherald, a Baltimore-based artist, won the $25,000 2016 Outwin Boochever Portrait Competition, hosted by the National Portrait Gallery, last year. The triennial competition helped bring Sherald’s work to a larger audience, and Sherald’s winning work, “Miss Everything (Unsuppressed Deliverance),” dominated an exhibition of finalists and other winners.