Henry enlisted in March of 1864; the war had been raging for three long years. During that time Henry had been a student at both Harvard and Yale as well as traveling in Europe. Henry was commissioned as a 2nd Lt. in the Massachusetts 5th Calvary. This unit consisted of volunteer Black soldiers and white officers. Coincidently, this is also the same regiment as Fredrick Douglas' son, Charles, who was the first sergeant, though he was in a different company than Henry. I read twenty-nine of Henry's letters to his parents during his time with the 5th Calvary. It is apparent that Henry had had little interaction with Black Americans prior to his service. His first letters are peppered with comments such as, "There is nothing like getting used to things. When I first joined the regiment, I rather shrank from contact with a negro, and could not look them in the face without breaking into a broad grin. Now I look on them as a matter of course. I have messed with them out of the same pork barrel, drank out of their canteens, lent them my blankets, borrowed their overcoats without a particle of  the fastidiousness which I used to feel towards my best friends before coming into the army."  While it is clear from comments made by his father in their letters that Henry held a more progressive view than his father, his experience was still one of the privileged white upper classes. As such he had never had the opportunity to put his principles to the test before. By the time of the Battle at Baylor's farm which Henry recounts in the letter above it is clear he has gained a new appreciation for the soldiers.