Pleasants enlisted as a private in Co. F of the 14th VA Infantry on May 12, 1861, joining at Lombardy Grove in Mecklenburg County, VA that day along with several other young men from Randolph-Macon College. He is listed as absent without leave, or desertion, on June 15, 1861. Although no further information on this enlistment exists, it's possible his father, a wealthy farmer in Amherst County, VA may have intervened as his two older brothers had died in 1847 while enrolled at Virginia Military Institute.
He enlisted again on March 26, 1862, this time joining the Amherst Light Artillery (VA) as a private. He was detailed as a clerk from August 15-October 1, 1862. Pleasants was transferred on April 8, 1863 to the 2nd VA Cavalry, but the transfer never occurred as he continued on the muster rolls of the artillery battalion. He was wounded and taken prisoner on September 19, 1864 at Winchester, VA, and Union surgeons amputated his leg. He was hospitalized in Martinsburg, WV until December and then sent to a hospital in Baltimore, MD, where he remained until January, 1865 when he was sent to the prisoner of war camp at Point Lookout, MD. Pleasants was released on June 2, 1865 after taking the oath of allegiance.
Pleasants returned home after the war. In 1870, he was living with his parents in Pedlar, Amherst County, VA and is listed as a "farm hand" in the census. He married Betty Nelson Davis and had 4 children between 1872 and 1878, but had died by the time of the 1880 census.
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