Now on Wikipedia -
The first judge of the W.D. Va was John G. Jackson, who married a sister of Dolley Madison, got shot in a duel while he was in Congress, and served on the commission that met at Rockfish Gap to decide where to locate the University of Virginia. He was appointed by James Monroe in 1819.
The second judge of the W.D. Va. - Philip Pendleton - was also on the Rockfish Gap commission - and voted for Lexington. Pendleton and his successor Alexander Caldwell were both recess appointments of John Quincy Adams. Jackson, Pendleton, and Caldwell were all from counties that are now part of West Virginia.
The fourth judge of the W.D. Va., Isaac Pennybacker, got a recess appointment from Martin Van Buren at age 34, resigned from the bench and became a U.S. Senator, and was named by James K. Polk to the very first Board of Regents of the Smithsonian Institution.
The fifth judge of the W.D. Va. was John White Brockenbrough, who started the law school at Lexington, and who opposed secession but quit his judgeship to join the Confederacy. After the war, Brockenbrough was the one who put to Robert E. Lee the idea of joining up with Washington College. Brockenbrough's successor, John Jay Jackson, Jr., the grandson of John G. Jackson, was appointed by Abraham Lincoln and held court in the western Union counties until they became West Virginia, then served on as district court judge in West Virginia for another forty years, becoming known as the "Iron Judge."
During the Civil War and after, there was no Western District of Virginia. The federal courts were consolidated into the District of Virginia, and the only judge was the abolitionist John C. Underwood. When the Western District was recreated, the next judge was Alexander Rives, who became a federal judge after he was not re-elected to the Virginia Supreme Court and lost an election for Congress. In the Congressional race, Rives got his opponent's civil rights restored without charging the usual fee, and bragged about it until the opponent paid the fee to shut him up on that issue.
After Rives retired, Judge Robert W. Hughes of the Eastern District, who had a home in Abingdon, came and heard cases in the Western District for a while. Hughes had gone over from being a rabid secessionist to becoming a Republican, a transformation that led to a duel with the writer of a newspaper editorial against him. Unlike Judge Jackson, Hughes walked away from his duel, having shot the newspaperman.
Rives was eventually succeeded by Judge John Paul. Judge Paul resigned his seat in Congress to take his judgeship, during the pendency of what would become a successful challenge to the outcome of the election.
To replace Judge Paul, Theodore Roosevelt gave a recess appointment to Henry Clay McDowell, a great-grandson of Henry Clay.
Of Judge McDowell, Judge Emory Widener told this story:
"Judge Henry Clay McDowell was presiding and, after a strenuous trial of several days, directed a verdict in favor of the defendant. The lawyer representing the plaintiff was Dan Trigg, a giant of the bar and the leading lawyer in Western Virginia. Judge McDowell bent over to tie his shoe, and the bench, at that time being elevated some two feet above the floor of the courtroom, screened him from the sight of everyone in the room. “Damn a federal judge anyhow,” Mr. Trigg exclaimed, being audible to all. Judge McDowell, of course, heard the remark, but remained stooped over and left the courtroom by a door just behind the judge's chair so that no one knew he was in the room. He later summoned all the other lawyers in the courtroom to his chambers and said that he had heard Mr. Trigg's remark. He asked the lawyers if anyone in the room knew that he had heard it. When the lawyers advised him that no one had, he stated the rule that lawyers had a constitutional right to cuss the judge and, since Mr. Trigg didn't know he had been heard, he was not going to be fined." "Remembering the Fourth Circuit Judges: A History from 1941 to 1998," 55 Wash. & Lee L. Rev. 471, 473 (Spring 1998).
McDowell practiced law for a while in Big Stone Gap and made the acquaintance of the author John Fox, Jr., who included him as a character in one of his books. McDowell served for thirty years, and his replacement, John Paul, Jr., was the son of his predecessor.
The second Judge Paul graduated from VMI, soldiered in Europe in World War I, and attended the Republican National Conventions in 1912, 1916, 1920, and 1924, before he was made U.S. Attorney in 1929 and District Judge in 1932. He was the last of the W.D. Va. judges to work alone. A second position on the W.D. Va. was created, but the first nominee didn't last long - the Senate rejected Floyd Roberts from Bristol, another recess appointee, by a vote of 72-9.
Roberts' nomination became a point of contention between Franklin Roosevelt and Senator Carter Glass from Virginia, about whether Roosevelt should consult with the Senators on federal positions in the Commonwealth. When Glass complained about reports that Roosevelt had promised veto power to Virginia's Governor James Price, and that Glass had not been consulted over the nomination of Roberts, Roosevelt responded that "Senator Glass that he had not been consulted over Roberts' selection, Roosevelt responded "that he was happy to consult Glass, but reserved the right to consult others, including, if he wished, 'Nancy Astor, the Duchess of Windsor, the WPA, a Virginia moonshiner, Governor Price or Charlie McCarthy.'" Glass and the Senate were unamused.
Roberts was succeeded by Armistead Dobie, who went on to the Fourth Circuit shortly thereafter, and among other things, wrote his own history of the judges of the District. Hon. Armistead M. Dobie, "Federal District Judges in Virginia before the Civil War," 12 F.R.D. 451 (1951,1952).