 He was one of a dozen sculptors invited to compete in the Pioneer Woman statue competition in 1927, which he failed to win.In 1927 he was elected into the National Academy of Design as an Associate member and became a full Academician in 1934.In 1932 Gregory produced 9 marble bas reliefs for Paul Cret's Folger Shakespeare Library in Washington, D.C. Each panel depicted a scene from a different play by Shakespeare.