Most 19th century wills start something like this: “I, John Smith, of the County of Clark and State of Kentucky, do make this my last will and testament . . .”
James W. Craddock’s will began a little differently — “Dear Sweet, The mails are stopped for the present . . .” This was the beginning of a letter to his sweetheart, Margaret Nicholas, in Winchester.
The letter was written on March 23, 1863, during the Civil War, while Craddock was serving in the Union army as commander of 16th Kentucky Infantry regiment at Lebanon. At the time he wrote the letter, his unit was aiding in the effort to repel Gen. John Pegram’s Confederate invasion of Kentucky. Craddock’s letter went on to state, “The rebels are now at Somerset, about seven thousand strong, advancing toward Danville. They will be in your County shortly.”
He concluded the letter with the following paragraph: “If I fall, D. A. Sayre & Co. in Lexington are my Bankers. Mr. Buckner also owes me. Whatever they say about it will be right. I want you to have whatever I may leave and to this extent this is my will.”
James Wesley Craddock was born in 1830 in Hart County. At the age of 18, he joined the Army during the Mexican War. He was assigned to Company D, 8th Infantry, but he enlisted too late to join the fighting in Mexico.
By 1860 Craddock had made his way to Winchester. That July he was residing at the National House, predecessor of the Rees House and Brown-Proctoria. At that time the hotel was residence to a dozen or so of the city’s unmarried businessmen. When war broke out, three of them would don Union blue and three Confederate grey.
In January 1862, James W. Craddock mustered in as captain of Company A, 20th Kentucky Volunteer Infantry. He joined a number of local men, including Col. Charles S. Hanson — a brother of Confederate Gen. Roger Hanson — who was in command of the regiment.
That April his regiment was in the bloody battle at Shiloh. They fought at the Peach Orchard, where Albert Sidney Johnston—a Kentuckian and Confederate general—was killed. The shocking number of casualties at Shiloh—more than 23,000—far exceeded any other battle of the war up to that time.
A few weeks later, while still at Shiloh, Craddock was promoted to colonel and placed in command of the 16th Kentucky Volunteer Infantry. Craddock’s regiment would serve in Kentucky. His first post was Munfordville, his hometown. That winter Gen. John Hunt Morgan launched his second Kentucky raid—the so-called “Christmas Raid.” In late October Union Gen. Jeremiah Boyle sent the 20th Kentucky to Bowling Green and Russellville. With the 16th still at Munfordville, Boyle hoped to drive Morgan into a trap, but the plan did not succeed. In December Craddock’s regiment, strengthened by the addition of the 7th Tennessee, was in pursuit near Lebanon, but Morgan slipped away again. The new year found the 16th still chasing Morgan; however, the infantrymen were unable to catch up to his fast-moving cavalry.
The day before Craddock wrote his March letter to Margaret, General Pegram had crossed the Cumberland River with his Confederate cavalry brigade. Craddock’s Union regiment was at Lebanon anticipating the path Pegram would take, but Gen. Quincy Gilmore’s forces stopped and defeated Pegram at Somerset on March 31.
As Craddock warned Margaret, the rebels did reach Winchester that month. Col. Roy Cluke led a small raid into Kentucky terrorizing the countryside—including his home county of Clark—before withdrawing safely to Tennessee.
Craddock’s letter to Margaret proved prophetic. He died at the Officer’s Hospital in Louisville on June 2. His cause of death was listed as “Haemorrhage from Bowels.” He was 33 years old. The officers of his regiment resolved to honor him as “a true gentleman, an earnest patriot, and a brave soldier . . . untimely called to fill an honored grave.”
Upon learning of Craddock’s death, Margaret took his letter to Clark County Court in June 1863. After Benjamin F. Buckner and Samuel G. Stuart testified that they recognized Craddock’s handwriting, the court accepted the letter as his will and admitted it to probate. No further mention appears in the probate records, perhaps because he left no estate here. The Army provided an inventory of the effects found at his death — clothing, a pistol, gold watch and $347 in treasury notes — which they sent to his brother, G. W. Craddock, a Frankfort attorney. Presumably, his brother sent it on to Margaret.
A few years later Margaret married Jesse T. Williams. He and Craddock had been two of the founders and charter members of the Winchester Independent Order of Odd Fellows — Hickman Lodge, No. 72 — in April 1861. This is the lodge that later erected the handsome building at 66 South Main Street.* In the 1860s Williams was the owner of a wool carding factory on East Broadway that later became Clark Chapel AME, then Jordan Electric, and has now been repurposed and as the Regeneration Distillery Company.
James W. Craddock was interred in Frankfort Cemetery. His sweetheart died 37 years later, in 1900. Margaret is buried beside her husband in Winchester Cemetery.
*After a disastrous fire in 2019, the Odd Fellows sold the building to 66 South Main, LLC. The owner, Perry Williams, DC, DACBSP, is a local chiropractor who is restoring this valuable downtown landmark.