Mosby's Confederacy Tours

About John Singleton Mosby

John Singleton Mosby was one of the great characters of his era. He, like many fellow citizens, was drawn reluctantly into the War Between the States; and, like some others from that period, became famous — or infamous, depending on your point of view — as a result his wartime activities.

Born December 6, 1833 in Powahatan County, Virginia, John S. Mosby was a sickly child — so frail, in fact, that he was relieved of most chores and other household duties as a child. Young John’s small size and general weakness led other boys to bully him and, faced with constant humiliation or defending himself, he began learning how to use his smaller size and speed against larger and more formidable opponents.

The young Mosby also studied the law as a result of conflict.

As a student at the University of Virginia, he was harassed by a fellow student, George Turpin, who had invited the same violinist to play at his party on the same night as John had invited to play at his. Turpin, in typical fashion, sent Mosby a noted indicating he would “beat the tar” out of Mosby the next time they met. Not eager for a confrontation from this large and angry man, Mosby armed himself with a pepper pistol and shot Turpin in the jaw as he lunged at Mosby one evening soon thereafter.

Mosby was convicted of malicious wounding and sent to the Albemarle County Jail in Charlottesville for a year and slapped with a $500.00 fine. With plenty of time on his hands, John asked the prosecuting attorney if he could read some of his law books, and the two began a friendship. Mosby was released from prison early thanks to a three hundred-person petition, also signed by several physicians who indicated Mosby was in poor health and may not live through the term of his confinement. He served as a law clerk for the attorney, who mentored Mosby until he could pass the Virginia Bar, which he did.

John Mosby met Pauline Clarke, daughter of a Kentucky congressman, not long after he began practicing law in rural Howardsville, Virginia. They fell in love and married, moving to Bristol, Virginia, just across the border from Bristol, Tennessee.

Mosby was 27 years old when war broke out in April 1861.

He joined his mother state to defend against what he considered invaders. He joined William E. “Grumble” Jones’ cavalry unit as a private, becoming a lieutenant when he became Jones’ adjutant. Not accustomed to military drilling and camp life, however, Mosby preferred to be in the field rather than in camp; when Fitzhugh Lee was voted by the men to lead them, Mosby resigned his commission.

In the spring of 1862, Mosby took the opportunity to become a scout for Confederate cavalry general Jeb Stuart.

He showed great promise early in the Peninsula Campaign by finding weakness along Union General George McClellan’s right flank, leading to Stuart’s famous “Ride Around McClellan.” The maneuver convinced “Little Mac” that he needed to pull his army back rather than continue “on to Richmond.”

Restless and bored with camp life when the armies went into winter quarters that year, Mosby convinced Stuart to allow him to take nine men to probe Federal picket posts in Northern Virginia in January 1863. His successful efforts resulted in Stuart endorsing Mosby’s proposal for a 15-member detachment a few weeks later.

Called a “horse thief” by Union Colonel Percy Wyndham of the 1st New Jersey Cavalry for Mosby’s guerrilla-like activities, Mosby took 29 men into Fairfax Court House during the night of March 8 – 9 in an effort to “bag” the Yankee colonel. After cutting the telegraph wires and capturing the operators, Mosby learned that Wyndham had been called to Washington and was not in town.

Mosby learned that a young brigadier general, Edwin Stoughton, was in town, and managed to take General Stoughton from his bed and make him a prisoner.

Mosby and his men left Fairfax Court House with 29 prisoners, including Stoughton. The news electrified the South, and Northern newspapers criticized Federal brass for being made to look like fools. This one event launched Mosby’s partisan career, which lasted through the end of “the wah”.

Mosby is mentioned and earned the praise of General Robert E. Lee more than any other officer in the Confederate Army.

Mosby and his men used deception, fear and pure audacity to offend, out-smart and outwit the enemy on countless occasions. Mosby was wounded four times during the war, at least one of which was life-threatening.

Mosby and his men recorded countless stories of daring and escape, of honor and courage and pride. Numbering fewer than two thousand men, they kept Federal forces many times their number in check, wary and worried that at any minute they would be captured by the “Gray Ghost.” Mosby chose to disband his unit rather than surrender on April 21, 1865. He and his family lived near Warrenton, where John worked as an attorney. After repeated run-ins with occupation forces, Pauline Mosby was able to obtain a pardon for her husband personally written by General-of-the-Army Ulysses S. Grant.

Despite his wartime deeds, Mosby was very much in favor of reconciliation following the war.

He became a Republican and stumped for Ulysses S. Grant in the presidential election of 1872. Because of the feelings toward Grant in the South following the war, Mosby suffered the loss of much of his law practice, and was even shot at as he stepped from a train one night in the fall of 1877. His wife, Pauline, as well as a son, had died in 1876, and living in the Warrenton area became too dangerous. Through Grant’s intercession with President Rutherford B. Hayes, Mosby was appointed U.S. Consul to Hong Kong, a position he held for seven years, 1878-85. His children stayed with relatives during those years.

Upon his return to the U.S., Mosby accepted a job with the Southern Pacific Railway, working out of an office in San Francisco, California. During these years, Mosby met a boy of about 10 years named George S. Patton, Jr., and the old veteran shared some of the secrets of guerrilla warfare with the boy who would one day lead the 3rd U.S. Army into combat in Europe during World War II.

Mosby held other jobs in his later years, especially with the Department of the Interior, where he caused many problems for cattle barons who used federal land to graze their cattle. Mr. Mosby served as an assistant attorney with the Justice Department from 1904-10, when he retired at age 76.

Mosby was one of the very first Assistant Attorneys General under the Department of Justice.

He lived until age 82, mostly healthy until the last two years of his life. Oddly enough, he died nearly impoverished, and is buried in the Warrenton, Virginia cemetery next to his wife and several children.

John Singleton Mosby - 1863

John Singleton Mosby – 1863

Mosby's Mother

Mosby’s Mother

General Stoughton

General Stoughton

Mosby's Rangers

Mosby’s Rangers


Mosby – 1915