Despite receiving one-third less pay and suffering mortality rates one-third higher than their white counterparts, approximately 186,000 Black men served as Union soldiers during the Civil War. Free Black people from the North and those who escaped slavery in the South also served as teamsters, moving supplies and burying dead soldiers. Their wagon lines were targeted by Confederate raiders who often killed captured teamsters or sent them into slavery. This scene of teamsters is one of Winslow Homer’s most enigmatic Civil War subjects. Its intended meaning and title have long been debated: perhaps these men look on the “bright side” of the future as they fight for the abolition of slavery. The title may also characterize the Union side in the Civil War, thus equating the Confederacy with darkness.