William Smith ( Virginia governor ) William " Extra Billy " Smith ( September 6 , 1797May 18 , 1887 ) was a lawyer , congressman , the 30th and 35th Governor of Virginia , and a Major General in the Confederate States Army during the American Civil War . On his appointment in January 1863 , at the age of 65 , Smith was the oldest Confederate general to hold field command in the war . Early life and politics . Smith was born in Marengo , King George County , Virginia . He attended private schools in Virginia and Plainfield Academy in Connecticut . He then studied law and was admitted to the bar and commenced practice in Culpeper , Culpeper County , Virginia , in 1818 . Two years later , he married Elizabeth Hansbrough Bell . They would have eleven children , several of which died in infancy or as young adults . He established a line of United States mail and passenger post coaches through Virginia in 1827 and then expanded the business into the Carolinas and Georgia in 1831 . It was in this role that he received his nickname . Given a contract by the administration of President Andrew Jackson to deliver mail between Washington , D . C . , and Milledgeville , Georgia ( then the state capital ) , Smith extended it with numerous spur routes , all generating extra fees . During an investigation of the Post Office department , Smith ' s extra fees were publicized by U . S . Senator Benjamin W . Leigh , and he became known as " Extra Billy " in both the North and South . Smith served as a member of the Senate of Virginia from 1836 to 1841 , when he resigned during his second term . Smith successfully contested as a Democrat the election of Linn Banks to the Twenty - seventh Congress and served from March 4 , 1841 , to March 3 , 1843 . He failed to be reelected in 1842 to the Twenty - eighth Congress . He then moved to Fauquier County . Smith served during the Mexican - American War as Governor of Virginia from 1846 to 1849 and was an unsuccessful candidate for election to the United States Senate during that period . He moved to California in April 1849 and was president of the first Democratic State convention in 1850 . He returned to Virginia in December 1852 and was elected to the Thirty - third Congress and to the three succeeding Congresses ( March 4 , 1853 – March 3 , 1861 ) . His brother - in - law Peter Hansbrough Bell was a Texas Revolutionary and Mexican War veteran who served as the third Governor of Texas from 1849 through 1853 . Electoral History . 1853 Smith was elected to the U . S . House of Representatives with 51 . 79 % of the vote , defeating Whig Edgar Snowden . 1855 Smith was re - elected with 78 . 01 % of the vote , defeating Independents P . Johnson Barbour and David Funsten . 1857 Smith was re - elected with 57 . 5 % of the vote , defeating now - American Snowden . 1859 Smith was re - elected with 49 . 36 % of the vote , defeating Independent Democrats Henry Wirtz Thomas and Henry Shackleford . 1863 Smith was elected Governor of Virginia with 47 . 77 % of the vote , defeating fellow Conservative Democrats Thomas Stanhope Flournoy and George W . Munford . Civil War . When Virginia seceded from the Union , Smith declined to accept a commission as a brigadier general because he rightly admitted he was " wholly ignorant of drill and tactics " . A few weeks after the war started , he was present during a Union cavalry charge at the Battle of Fairfax Court House ( June 1861 ) . He took command of the Confederate troops after the death of their commander John Quincy Marr , and found he enjoyed the experience . He requested a commission and was appointed colonel of the 49th Virginia Infantry regiment just three days before the First Battle of Bull Run , where the regiment and new commander performed well . Smith served in the Confederate Congress in 1862 , but returned to the 49th Virginia at the start of the Peninsula Campaign . He was wounded at the Battle of Seven Pines and his regiment received favorable notice in his commander ' s report . During the Seven Days Battles the regiment was lightly engaged , but he and his command again were described as having " characteristic coolness " and " fearlessness . " He was known for expressing contempt for West Point graduates ( " West P ' inters " ) and their formal tactics , recommending common sense to his men instead of a military education , and distinguished himself with his unorthodox field uniform , including a tall beaver hat and a blue cotton umbrella . At the Battle of Antietam , Smith temporarily commanded a brigade in Maj . Gen . Jubal Early ' s division . He was wounded three times , but continued to command , and Maj . Gen . J . E . B . Stuart wrote that he was " conspicuously brave and self - possessed . " By the end of the battle he had to be carried from the field . In recognition of his performance , he was promoted to brigadier general as of January 31 , 1863 . He commanded a brigade in the Battle of Chancellorsville , but achieved no distinction in this role . By the time of the Gettysburg Campaign , Smith ' s superiors were leery of his performance , but had to provide subtle influence because he was the former governor and at the time the governor - elect of Virginia . Early directed Brig . Gen . John B . Gordon to keep close contact with Smith and effectively exercise a joint command over their two brigades . During the Battle of Gettysburg , Smith refused to pursue retreating Union XI Corps troops , concerned that a Union force was approaching from his left , which was a significant reason that the Confederates failed to attack and take Cemetery Hill on July 1 , 1863 . Smith was the oldest general on the field and fought ( unsuccessfully ) the oldest Union general , Brig . Gen . George S . Greene , at Culp ' s Hill on July 3 , 1863 . He was the only general not commended in Early ' s official report and , as a result , decided to resign his commission on July 10 . He nevertheless received an essentially honorary promotion to major general and Assistant Inspector General on August 12 and performed recruiting duty in Virginia . Postbellum career . Before the Gettysburg Campaign , Smith was elected again as Governor of Virginia and served from January 1 , 1864 , to the end of the war . He was among the first Southern governors to advocate arming blacks to provide manpower for the Confederacy , and he occasionally returned to the field to command troops in the defense of Richmond . He was removed from office and arrested on May 9 , 1865 , but was paroled on June 8 . He returned to his estate , " Monte Rosa , " ( Later renamed " Neptune Lodge " ) near Warrenton , Virginia , where he engaged in agricultural pursuits . At the age of eighty , he became a member of the Virginia House of Delegates ( 1877 – 79 ) . He died in Warrenton and was buried in Hollywood Cemetery , Richmond , Virginia .