"Six feet, four inches tall, splendidly proportioned, with a magnificent suit of brown hair and whiskers, graceful as any man who ever rode to war, as brave as the bravest, calm, cool, fierce in danger, his presence was always an inspiration to his followers."
Cluke is best known for the stunning Kentucky raid he led in 1863, which Young described in his book Confederate Wizards of the Saddle. From McMinnville in central Tennessee, Cluke took a small handpicked brigade of 750 men over 800 miles on a dangerous mission deep into Union occupied Kentucky. With haversacks filled with six days' rations, they began their march on Feb. 14 amid showers of rain, sleet and snow. They rode 110 miles to the Cumberland River near Somerset, pushed on to Mount Vernon and Richmond in a blinding snowstorm, then drove a Federal cavalry unit back across the Kentucky River at Combs Ferry. At that point, Cluke furloughed nearly half his men, allowing them to visit their families in the neighborhood in hopes they could obtain fresh mounts, clothing and food. Eighteen-year-old Mattie Wheeler of Winchester wrote in her diary that many of Cluke's men came into town on Monday, Feb. 23.
By Feb. 24, Cluke had captured Mount Sterling and established his base there. Though under strength and camped in the midst of superior forces, he had Union commanders convinced that his was the advance unit of a 10,000-man Confederate army. This ruse was soon discovered, and Col. Ben Runkle's 45th Ohio Regiment drove Cluke from Mount Sterling. After the furloughed men rejoined Cluke, he recaptured the town, but was driven off again and retreated to Hazel Green, and from there to Salyersville, where freezing rains poured from the sky and many of his men took sick. On March 19, with only 500 effectives in camp, Cluke's scouts reported that he was completely surrounded. More than 3,000 Union troops were said to be advancing on his position.
Knowing he was facing a desperate situation, Cluke responded with a daring move that saved his command from certain capture. He wheeled around, slipped through the line of troops pressing his rear, and made a forced march in the rain and snow to Mount Sterling, which he recaptured on March 21. There he took nearly 300 prisoners and seized 220 wagons, 500 mules and 1,000 rifles. Before beginning the return trip to Tennessee, he sent a dispatch to Gen. Morgan stating, "My command is elegantly mounted and clothed, in fact in better condition than they ever have been."
Cluke's unit was actively engaged in the war until his capture in July 1863 during Morgan's Great Ohio Raid. Roy S. Cluke died, probably of diphtheria, at the Union prison on Johnson's Island, Ohio, on Dec. 31, 1863. He asked to be buried beside his mother in the old Stuart graveyard in Clark County. Cluke was later reinterred in the Lexington Cemetery, where he lies close to John Hunt Morgan, Roger Hanson, and John C. Breckinridge.
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