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Woodruff's best-known work is the three-panel Amistad Mutiny mural (1938), which he completed for the Savery Library at Talladega College. The first of the mural's three panels, entitled The Mutiny Aboard the Amistad, 1839, depicts a revolt in which Mende slaves took over the Spanish ship Amistad. The second panel, The Amistad Slaves on Trial at New Haven, Connecticut, 1840, depicts the ensuing United Supreme Court Case, United States v. The Amistad. The third panel, The Return to Africa, 1842, shows the former slaves' later repatriation to Africa.

The murals are an example of Woodruff's mastery of composition. For example, in the first panel:

"The power of the combat is accentuated by the figure groups which give the composition its balance and visual stability. The circular motion of the bodies increases the drama of the struggle...The figures are designed in an overlay fashion so that they are seen as one complete unit moving from the left bringing the eye around to the escaping sailor, who reappears in the second panel as the accuser."

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In the Spring of 1938, Woodruff was commissioned to work on a series of murals for the lobby of the Savery Library at Talledega College in Alabama. These works would commemorate the Amistad Mutiny of 1839 and the founding of the college in 1867.