When the United States entered World War I in 1917, Flannagan quit school and joined the Merchant Marines.
"[5] Back in the United States by 1934, Flannagan found work with the PWAP, the Depression-era government program that sponsored American artists.
He received this position, his only means of support at the time, through the influence of Juliana Force, the first director of the Whitney Museum of American Art.
Force and Gertrude Vanderbilt Whitney had been longtime supporters of the sculptor, recognizing that he was a profoundly troubled man but also an exceptionally talented artist.
Flannagan's earlier work had been Gothic images of suffering, attenuated free-standing figures in wood handled like bas-relief with affinities to both German Expressionism and primitive Christian art.
In the next decade his style broadened, becoming more ample and rounded; in place of expressionist torment, he substituted an effective and personal motif...his subjects were almost exclusively drawn from the animal and insect kingdom, although he executed a number of sensitive portraits and figure compositions.
[11]Hunter compared Flannagan's sensibility to "the visionary, romantic art of Albert Pinkham Ryder and Morris Graves," adding that "the microscopic sensibilities of such American poets as Emily Dickinson and Marianne Moore support and confirm the native authenticity of Flannagan's touching, creatural realism.