Family Stories

John Calhoun Singleton Mystery Man No Longer – Mercer County

In commemoration of her many virtues, this monument is dedicated to Amanda Singleton, wife of Dr. J. A. Thompson, February 4, 1819 – March 9, 1878.  J. Addison Thompson, A.B., M.D., Fellow of the Ohio Medical Society, July 4, 1805 – April 2, 1881.  Spring Hill Cemetery, Harrodsburg, Mercer County, Kentucky.

About seven years ago I first visited Spring Hill Cemetery in my hometown of Harrodsburg, Mercer County.  I couldn’t imagine the delight in my own back yard.  Spring Hill is beautiful any time of year.  There are large and small stones, many old families represented, as well as new.  One stone toward the back of the cemetery caught my eye.  It is a large, imposing stone, dedicated to the deceased wife of Dr. Joseph Addison Thompson – Amanda Singleton Thompson.  Three stones are behind the large one, one each for Dr. Thompson and wife, and one for John Calhoun Singleton – 1843-1863.  Try as I may I could find nothing about this young man.  It was quite likely, due to the date of his death and his age, he was a casualty of the Civil War.  This has bothered me for years.

Now that I have Fold3 and several other resources I tried my luck again – and met with success this time.

John’s father, Richard Singleton, was born March 26, 1817, in Wilkinson County, Mississippi, the son of Hiram Singleton and Susan Richardson.  In May of 1836, in Mercer County, Kentucky, he married Mary Ann McAfee, daughter of John Armstrong McAfee and Mary Dicey Caldwell.  How did Richard and Mary meet?  Perhaps we will never know.  Mississippi seems a long way from Kentucky – especially in 1836.

It was a short marriage, Richard and Mary had two sons before his death in 1842 – William Francis born about 1839 and John Calhoun born May 8, 1843 – possibly after the death of his father?  Mary married Joel Price Williams, in Mercer County, September 22, 1848, and with him had one son, Joel P., Jr., all listed in the 1850 census of Mercer County.

After Joel’s death in 1855, Mary McAfee Singleton Williams married Dr. Benjamin King.  Another question about how Mary met Dr. King – he was a resident of Anne Arundel County, Maryland, until his death in 1888 at the age of 91, one year after Mary died.  Dr. King was an army surgeon most of his life, having entered as surgeon’s mate of the seventh infantry, October 14, 1818, and after 45 years of service was placed on the retired list November 9, 1863.

Now let’s return to John Calhoun Singleton.  In 1859 J. G. Brown, of the 5th Congressional District of Kentucky wrote a letter to James Buchanan, President of the United States at that time, requesting John Calhoun Singleton be given the vacancy available at the Military Academy at West Point.  Brown commends young Singleton as ‘the best person for the appointment,’ stating he is a ‘youth of great sprightliness and will reflect credit about his district and himself if the place shall be given him.  It will be very gratifying to his relatives – a numerous and influential family and among the oldest and first citizens of our state.’  He is speaking of Mary McAfee, John’s mother, since her grandfather was Samuel McAfee, one of the original McAfee brothers in Mercer County long before it became a state.

John Singleton was sent to West Point to fill the vacancy, named as such March 1, 1861, and arrived there June 1st of that year.

Life was not to give John his dream of being a cadet in the military academy.  The Civil War was to change all lives.

Due to refusing to take the oath of allegiance to the Union, John C. Singleton wrote the following letter:

Harrodsburg, Mercer County, Kentucky

September 23rd, 1862


I write to ask an appointment as Cadet in the National Military Academy to be established by the Confederate States.

I base my claim to the appointment on the fact that I was Cadet at West Point and dismissed for refusing to take an oath of allegiance to the Northern Government.  I was appointed ‘at large’ on the 1st of March 1861 by (then) President Buchannan; I accepted at the Point early in June and left it about the 1st of September ’61, when the oath was offered to the Corps, all of whom took it with the exception of Mr. Dunlap (now Captain in Gen. Kirby Smith’s staff) and myself who were dismissed.

It may seem strange that I should have permitted a whole year to have passed without having either thrown myself

into the throng or made this application.  When I left West Point, it was with the intention to make my way to the Confederate Army; but when I reached my home in Washington City, I found my mother bitterly opposed to my making the attempt.  I was the only one of four boys not in the C.S. Army, my father was threatened with arrest and he once in prison, I was the only one left to take care of my mother and sister.

Such considerations kept me with my mother for a year, but when I found that my native state was to be occupied and have a chance to redeem herself, I could stay no longer but hastened out and got to Lexington on the night of day on which the battle at Richmond was fought.


J. C. Singleton.

I have on brother and two step-brothers in the army or had two – one of whom fell at Shiloh – Ben King.

                         Respectfully your obedient servant,

J. C. Singleton

John stopped to see his mother and step-father in Washington, D. C., on his trip from the Military Academy.  His mother must have been horrified to think he would enter the war, since his brother and two step-brothers were already in the thick of the fight, and one fallen at Shiloh.

After a year, he returned to Kentucky to hopefully be appointed to the military academy to be formed by the Confederate States.  As this did not occur, John C. Singleton joined the 6th Regiment of the Confederate States that was mustered into Confederate service in September 1862.  For a time, the unit skirmished in Kentucky attached to Buford’s Brigade, then it fought with J. H. Morgan.  Its commanders were Colonel J. Warren Grigsby, Lieutenant Colonel Thomas W. Napier and Major William G. Bullitt.

A letter was sent by Col. J. Warren Grigsby April 3, 1863, which gave recommendation for John Singleton to be ‘be appointed Second Lieutenant of Co. G of my regiment in conformity with Sec. 10 of An Act to further provide for the Public Defense, approved April 16th, 1862. 

Sergeant Singleton has been distinguished for his seriously braving and general good conduct since he first joined my command and in the fight near Milton, Tennessee, on the 29th bore himself with great gallantry.

Co. G is now without a Commissioned officer as I have heretofore required their resignations for inefficiency and with the exception of the appointment herein respectfully recommended, I do not propose to have their places filled up until the Co., which has been assigned for duty temporarily with Co. D has been remixed up.

I respectfully recommend

that the appointment of Sergeant Singleton as Second Lieutenant be dated from March 20th, 1863.’

At first the 6th Regiment, Kentucky Cavalry, Confederate States, was attached to Buford’s Brigade, then it fought with General John Hunt Morgan.  Therefore, I believe that John C. Singleton was with Morgan when he burned the courthouse at Lebanon, Marion County, Kentucky, July 5, 1863.  They didn’t consider what travesty that would be for the fervent genealogists to come in later years!

Morgan headed north to try to invade Ohio, crossing at Harrison on July 13, pursued by several columns of Union cavalry.  It was on this day that John Calhoun Singleton died.  I could find nothing in his Civil War records that indicated where or how he died, but with the information I found about the regiment, this must be true.  Such a sorrowful end for a young man who ‘bore himself with great gallantry.’

John Calhoun Singleton, Captain C. S. A., born May 8, 1843, died July 13, 1863.

Now to the question of why his body was returned to Kentucky?  Perhaps his mother wanted him buried in his native soil.  Amanda Singleton Thompson was his aunt – sister to his father Richard.  I think it very fitting he is buried with Aunt Amanda and Uncle Joseph.  They never had children, so this nephew was treated as a child in death.

What made this young man so eager to join in the war?  Perhaps it was the blood running in his veins from his great-grandfathers who fought in the Revolutionary War – Captain Richard Singleton of South Carolina, Captain Arthur Richardson of North Carolina, Major David Caldwell and Samuel McAfee defending Kentucky lands attached by the British and Indians.

After seven years I am happy to know more about this young, courageous man who gave his life during the war.

The sunshine of his native sky,

Smiles sadly on him here,

And kindred eyes and hearts watch by

The hero’s sepulcher.

1 reply »

  1. Thanks for the great article. I recently ran across Singleton at Spring Hill and wondered about his story. Turns out, not only was (then) Lt. Singleton with Morgan at Lebanon, he was wounded in action there on July 5th. According to an article in the July 15, 1863, edition of the Louisville Daily Journal (page 1), Lt. Singleton sustained a flesh wound of the right thigh during that engagement.

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