Dr. Kean reportedly declined Thomas Jefferson's offer of a professor's chair at the newly established University of Virginia (from which his grandson would receive both undergraduate and legal degrees), and started a medical tradition which would include Robert G.H.

Airy by his maternal aunt, Miss Elizabeth Hill, until his father, John Vaughan Kean (1803-1876) remarried in 1837 and brought his son back to his own Caroline County plantation, "Olney".

After the Battle of Gettysburg, on July 7, 1863, Kean wrote that Lee had captured 40,000 of the enemy, but remained skeptical because of the lack of official news.

The following day, he received those reports, and wrote "The week just ended has been one of unexampled disaster since the war began.

[10] During the Confederate evacuation of Richmond in April 1865, Kean took the War Department's papers to South Carolina.

He noticed devastation, which he attributed to the abolition of slavery, characterizing manumission as "the greatest social crime ever committed on Earth.

"[12] Particularly after the death of General Robert E. Lee, Kean became active in the Lost Cause, as most prominently espoused by former Gen. Jubal Early, who also maintained a residence in Lynchburg and published the Southern Historical Society Papers, to which Kean contributed in 1876 (one paper using the military or honorific title "Colonel).

Kean also served on the vestry of St. Paul's Church, and on the Standing Committee of the Episcopal Diocese of Southern Virginia after its creation.

At the time of his death, only former Confederate Postmaster-General Reagan of Texas was living and held a higher civil office in the Confederacy bureaucracy.