Masters struggled to hold on to literature, his heart's aim, as did the figures in the Spoon River cemetery. Masters dutifully read law with his father because his father, disdainful of poetry, insisted that his son study law; he achieved bar certification in 1891. He joined a Chicago law firm allied with attorney Clarence Darrow and specialized in labor and industrial casework. After his marriage to Helen Jenkins, mother of their three children, he often visited Spring Lake, Wisconsin, where he established a sizable farm and he escaped his life as a lawyer.
While successfully pursuing legal work and supporting populist political candidates in Chicago, Masters submitted unoriginal poems to Chicago newspapers. He also published A Book of Verses (1889), a derivative work of belles lettres, and an anti-war pamphlet, The Constitution and Our Insular Possessions (1900), later collected in The New Star Chamber and Other Essays (1904). For a decade, he worked on a series of plays, including Maximilian (1902), Althea (1907), The Trifler (1908), The Leaves of the Tree (1909), Eileen (1910), The Locket (1910), and The Bread of Idleness (1911). During this time, Masters was acquainted with novelist Theodore Dreiser, editor Harriet Monroe, and poets Amy Lowell, John Masefield, Vachel Lindsay, and Carl Sandburg.
