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- Letter from James B. Heyward to an unknown recipient carried by one of his overseers, C. R. Hains, who is reporting for duty. In his letter, James protests the conscription of plantation overseers into the Confederate army claiming they "have large numbers of negroes under their charge" and that "in his absence the timid become panic struck and the bold mischievous." He also argues that the overseers "by means of espionage know every thing that is going on" and that well run plantations can better provide supplies to the war cause. 4p. November 12, 1861.
- Letter from E.C. DuBose, writing for Captain Chambers, to James B. Heyward concerning Nathaniel Heyward's body servant. Lt. DuBose writes to James that "your Boy John is with us" but that it wouldn't be safe to send him on "without some white person as the whole country is over run by straglers (sic) and he may be taken up." 1p. October 7, 1862.
- Letter from Daniel Heyward Hamilton to James B. Heyward about the loss of James' son, Nathaniel, and the plans to return Nathaniel's body servant to James. Daniel writes that his own son was wounded by his side in a previous engagement. 3p. October 25, 1862.
- Letter from John W. Chambers to James B. Heyward concerning his slave, John, the body servant of James' deceased son Nathaniel. Captain Chambers writes that sending James' servant to Richmond is problematic because of the heavy travel on the rail route and that "it is with difficulty a white person can engage a passage and any servant would be compelled to walk." 1p. November 1, 1862.
- Letter from James B. Heyward in Columbia to Dr. D.W. Ray, trustee for the late owner whose land James had verbally agreed to rent. James is anxious to move his slaves there for safekeeping but is worried the trustee had no knowledge of the agreement between James and the recently departed owner. James also mentions that he must hasten back to the low country "as my property there is in peril from the proximity of the enemy." 2p. December 19, 1864.