George H. O'Connor: Georgetown's Troubadour to the Presidents

When George H. O’Connor (1873-1946) died at the age of 72, the Washington Post wrote simply “he was almost beyond a doubt the most popular man in Washington.” A lifelong Washingtonian, he had attended St. John’s Academy in Alexandria (1888-91) and earned an LL.B. from the National University Law School in 1894.
This photograph shows members of Georgetown Law—where O’Connor became a “special student” in 1895—standing in front of Healy Hall. O’Connor is in the first row at the far right. 

O’Connor was by day a successful lawyer and businessman. He was admitted to the DC bar in 1895 and to the bar of the Supreme Court in 1918. His major employment was with the District Title Insurance Company, first as vice-president (1907-41) and later president (1941-1946). As distinguished alum, O’Connor was congratulated by Georgetown President William Coleman Nevils, SJ when he was made a “Kentucky Colonel” in 1934.

What made O’Connor “the most popular man in Washington” was not his work as a lawyer or title officer; rather it was his long career on the stage. O’Connor first appeared in the Washington press in 1883 (at the age of nine) as a member in a “juvenile masque carnival” at Professor Sheldon’s Dancing Academy. His interest in theater and music continued while at Georgetown where he was a frequent soloist with the Glee Club. This 1900 program of the Glee, Banjo and Mandolin Clubs shows O’Connor performing a hymn in the new and fashionable “Rag-Time” style.

Sometime around 1900 O’Connor and three friends formed the Birenomore Quartette, and O’Connor soon became a regular entertainer at events hosted by the Gridiron Club, the National Press Club, the Alfalfa Club, the Knights of Columbus, the Bar Association, and various other men’s organizations. But his greatest claim to fame was as the “Troubadour to the Presidents.” He was also a major recording artist for the Columbia Graphophone Company in the mid-1910s. 

The photographs above (5) are publicity shots, one showing O’Connor enjoying his own recording. George O’Connor has been described as one of the first musicians to record “blues-like” music.
O’Connor’s professional and entertainment lives were thoroughly intertwined.

Here we see (7) a letter informing O’Connor that happy memories of his performances aided in the admission of a friend to the New York bar. In 1938 O’Connor accompanied President Roosevelt to Warm Springs, GA (probably as an entertainer). 

(8) O’Connor prepared a telegram to his wife describing the trip and(9) a postcard home to his son showing the “Little White House.” By the time of his death O’Connor had entertained seven sitting Presidents, starting with William Taft.

(10) Harry Truman sent this letter of condolence to O’Connor’s widow.