2 Nov. 1827–29 May 1894
Thomas Webb, lawyer and railroad executive, was born in Hillsborough, the youngest son of Dr. James and Annie Alves Huske Webb. His father, Dr. James Webb, practiced medicine in Hillsborough for fifty years. Numerous students read medicine with Webb, who also initiated and underwrote two famed Presbyterian schools in Hillsborough, Miss Mary W. (Polly) Burke's School and the Burwell Female School. Thomas Webb's mother, Annie Alves Huske Webb, was a granddaughter of the Scotsman James Hogg, a University of Edinburgh graduate, merchant, and realtor who immigrated to North Carolina in 1774 setting out with a shipload of 280 persons. Hogg was on the committee to establish The University of North Carolina, served as president of the board of trustees, and was a large land donor to the university, where Thomas Webb was graduated in 1847.
On 16 Nov. 1854 Thomas married his second cousin, Robina Norwood (18 July 1835–24 Dec. 1919), the second daughter of John Wall and Anna Bella Giles Norwood. The Webbs lived at Norwood's Grove (later known as Poplar Hill and now known as Oconeechee Farm) with Robina's parents in the ancestral home built by James Hogg. For several years Webb was a clerk and master-in-equity before going into partnership with his father-in-law in the firm of Norwood and Webb, which did a large business in Orange and adjoining counties. In Hillsborough Presbyterian Church he was ordained an elder in 1855 and served as clerk of session in 1861.
About 1858, after two children were born, Thomas and Robina gathered material for a new home to be built on the knoll between the Hogg-Norwood house and the mineral spring. In the meantime, they moved to the Webb house on Queen Street, the one originally built by James Webb for his children's schoolroom. Due, however, to the Civil War, their new house was never constructed.
At a meeting of the Union party in Orange County for the purpose of nominating delegates to the proposed state convention, Thomas Webb served on the committee of nineteen representing the different sections of the county. After the Civil War began the president of the North Carolina Railroad, Charles S. Fisher, who had raised and equipped the North Carolina Sixth Regiment, was killed leading his unit on Rickett's Battery at Manassas during the first major encounter of the war on 21 July. The state nominated Webb president of the North Carolina Railroad, which he managed through the years of strife.
The Hillsborough Soldiers Aid Society, a group of ladies, gave food and aid to wounded soldiers traveling on the North Carolina Railroad. In 1861 the Orange County Court assumed responsibility for the support of the destitute families of its soldiers and managed this by dividing the county into districts, with an appointed commissioner for each district who assisted these needy families and reported all disbursements to Thomas Webb, who was treasurer of the soldiers' fund. In 1862 the wife of a Confederate soldier received $1.50 a month.
Federal forces failed to capture the North Carolina Railroad during the conflict, but the line suffered from both enemy attacks and the state's inability to provide adequate maintenance, including the replacement of wornout rails and crossties.
In the 1870s, after managing to endure the havoc and ruin of the war, the Webb family suffered an even more dreadful time as Robina lay in bed with inflammatory rheumatism and Thomas was brought home paralyzed. For about eighteen years before his death, this handsome and learned man was an invalid. He was buried in the Old Town Cemetery in the family plot, where his wife also was interred in 1919. Of the Webbs' nine children, seven survived to adulthood: Margaret Taylor (22 Sept. 1855–1939), John Norwood (25 May 1858–1934), Anna Bella Giles (10 Sept. 1860–8 Feb. 1935), Alves (24 Dec. 1865–1924), James (23 Aug. 1868–23 May 1927), Thomas (5 Mar. 1871–1939), and Robin (24 May 1874–27 Mar. 1941). The two who died young were Benjamin Huske (6 July 1863–7 July 1866) and Eliza Plumer (29 Oct. 1876–26 Mar. 1877).