This is a biographical sketch that marshals previously unexamined primary sources to tell the story of Henry Dana, member of the Boston elite and grandson of both Richard Dana and Henry Wadsworth Longfellow. Despite his wealth, privilege, and lineage, Dana stuck up for unpopular causes throughout his life including the defense of Sacco and Vanzetti, Pacifism in WWI, and the Soviet project. In an effort to establish the forgotten Dana among the constellation of early 20th century Soviet sympathizers, this paper provides some educated guesses about how Dana came to acquire such unpopular sympathies and examines the consequences Dana faced in his lifetime for doing so.