Thomas Ragland (ca. 1798–1825), soldier and attorney, was a native of Virginia. He enlisted in the United States Army as a private in 1813 and rose to the rank of third lieutenant by 1815. That same year Ragland entered the United States Military Academy at West Point. Even as a cadet, he was made an assistant mathematics instructor, but he became dissatisfied with condititons there and left West Point and the army in 1819. During his time at the Military Academy, Ragland formed a friendship with Nicholas P. Trist, TJ’s family friend and future grandson-in-law. In March 1820 Ragland visited TJ at Monticello and was hired immediately thereafter to teach mathematics in Gerard E. Stack’s Charlottesville Academy. While in Charlottesville he boarded with Hore Browse Trist and Francis Eppes and studied law under Valentine W. Southall. In September 1820 Ragland left the Charlottesville Academy and went to Hanover County to continue his legal studies near his family. By 1821 he was living in what is now West Virginia, first near the town of Cameron and settling by 1823 in Romney, where he practiced law and joined the Romney Literary Society. Ragland died in Romney (Hu Maxwell and Howard L. Swisher, History of Hampshire County West Virginia From Its Earliest Settlement to the Present [1897], 427, 433; Heitman, U.S. Army description begins Francis B. Heitman, comp., Historical Register and Dictionary of the United States Army, 1903, repr. 1994, 2 vols. description ends , 1:812; Patrick G. Wardell, Genealogical Data from United States Military Academy Application Papers, 1805–1866 [2002], 1:12; ASP, Military Affairs, 2:24; Ragland to Nicholas P. Trist, 18 Mar. 1820 [NcU: NPT]; Hore Browse Trist to Nicholas P. Trist, 23 Mar. 1820 [NcU: NPT], and 14 Apr., 3 Aug., 13 Oct. 1820 [DLC: NPT]; Elizabeth Trist to Nicholas P. Trist, 28 Mar. 1820 [DLC: NPT]; Wilson M. C. Fairfax to Nicholas P. Trist, 17 May 1821 and 21 Oct. 1823 [NcU: NPT]; Washington Daily National Intelligencer, 16 Sept. 1825).

The committee of (5) cadets that led a protest in 1818 against a commandant of cadets at the United States Military Academy at West Point consisted of Ragland, Charles Rutledge Holmes, Nathaniel H. Loring, Charles R. Vining, and Fairfax’s son Wilson M. C. Fairfax. They were ordered out of the academy and tried by a court-martial in 1819. After it concluded that it lacked jurisdiction, they resigned from the army. Later that year the five petitioned the United States Congress for relief, “complaining of manifold acts of tyranny and oppression on the part of the Superintendent” at West Point and “praying that an enquiry may be had into its state, management, laws, regulations, and transactions.” The following April the House of Representatives declined to act on their behalf and gave them leave to withdraw their petition (Stephen E. Ambrose, Duty, Honor, Country: A History of West Point [1966], 77–9; Ragland, Defence before a General Court-Martial, held at West-Point, in the state of New-York, in the month of May, eighteen hundred and nineteen [Newburgh, N.Y., 1819; possibly Poor, Jefferson’s Library description begins Nathaniel P. Poor, Catalogue. President Jefferson’s Library, 1829 description ends , 11 (no. 689)]; ASP, Military Affairs, 2:5–30, 138–9; JHR description begins Journal of the House of Representatives of the United States description ends , 13:79, 396, 405 [27 Dec. 1819, 11, 14 Apr. 1820]; Louise Pecquet du Bellet, Some Prominent Virginia Families [1907], 2:178–9).