In 1911, Bailey married the former Alice Chase, and the two would have four children. In Portland he continued practicing law through 1915 with the firm Platt and Platt. Beginning that year he was a deputy attorney general, serving until 1920. In that role he handled a variety of land fraud cases and helped to draft legislation that helped the state of Oregon better protect its state-owned land holdings. From 1920 to 1933 he returned to private practice at the firm Perkins and Bailey.