Colonel James Hillyer Holloway

by Edmund Starling, 1886


The subject of this brief biographical sketch, so well known in Henderson County, and so universally esteemed for his purity of character and many social qualities, was born in the then town of Henderson the first day of February, 1835. His eyes first beheld the light of the world in the old frame building yet standing on the corner of Fourth and Main streets. At the time of his birth his father, William S. Holloway, was associated with Samuel Stites as merchant in the general dry goods business. When at the age of two years his father purchased what is now known as the Adams farm, one mile west of the Owensboro road, and adjourning the farms of William S. and Samuel Elam. While on this farm, and before he was large enough, or old enough to do labor, it became a part of his daily duties to martial the young negroes, and, with them, driver a large flock of turkeys to the tobacco field, for the purpose of destroying the army of worms which prey with such wanton gluttonness upon the broad leaves of that valuable plant. It was here, while marching and counter-marching the little negroes, and moving the turkeys by the right and left flank, charging the worms in one section of the field, and then in another, that he first inherited a taste to command This taste grew upon him, as we shall see, until it eventuated in producing a most worthy and brave commander in defense of his country during the war between the North and the South. While a small boy upon his father's farm, he first learned the value of the alphabet and multiplication table. His aunt, Miss Eliza Hillyer, who possessed a strong taste for teaching and a peculiar charm of imparting knowledge to the young, organized a country school in a rude log cabin upon this farm, and was patronized by the surrounding neighborhood, numbering at that time only three for four families. He continued under the educational guidance of his aunt for a year, when his father, observing his rapid progress, brought him into the town that he might receive advantages beyong those offered at a small country school. He was placed to board at the residence of his aunt, Mrs. Lucy Ann Gayle, then living in the old two-story log building on the corner of Elm and Third streets, known as Blackberry Hall, where he remained during the school week, going home Friday evenings and returning to town Monday mornings. At Mrs. Gayle's he roomed with John and William J. Marshall and William and Charles T. Starling, all boys, his senior in years. His education was placed under the supervising care of Rev. John McCullagh, who was at that time teaching in the old town Seminary lot, opposite the Cumberland Presbyterian Church, on Fourth street. After boarding in town for a year, his father concluded to test his power of guiding a mule, so he placed at his disposal a favorite animal, which he was appointed to ride into town each morning and to return in the evening. Many a time the young soldier was dumped on the roadside, and almost as frequently thrown into a mud-puddle; fortunately, at no time, however, was he ever disabled. He, like almost all boys, was fond at times of riding fast, and, upon more than two or three occasions, while in a sweeping gallop, his mule was known to stop, hump his back and stand to witness young Holloway's passage through midair and final lodgment upon terra firma. Young Holloway continued to live with his father upon the farm until he had arrived at the age of thirteen years, riding to town during school days and working on Saturday in the tobacco patch.

Mr. Samuel Stites, his father's former partner, laving been a most successful merchant, and having amassed a large fortune for those days, sold his entire interest in the dry goods business to the father of young Holloway. Mr. Holloway then sold his farm and removed to town, taking charge of his new purchase. He continued his son at school until he was eighteen years of age, when he was taken as a clerk in the firm name of Evans & Holloway. He continued to clerk for this firm for five years, when he resigned to accept a similar position in the book and stationary business with his uncle, Philo H. Hillyer. January, 1860, the firm of Evans & Holloway was dissolved, Thomas Evans retiring. Mr. Holloway thereupon proffered Wm. A. Hopkins, a young man of splendid business capacity and high moral culture, and who had been in the employ of the old firm for several years, and his son, James, the subject of this sketch, a partnership. The proposition was accepted, and the new firm organized under the name and style of Wm. S. Holloway & Co. In 1860, under and by the authority of an Act of the Kentucky Legislature, a State Guard or military organization was established in Kentucky, to be under the command of General Simon Boliver Buckner. Just why this organization was brought to life at that time, what were the necessities for it, and what the objects to be obtained, is a matter of historical conjecture. It is enough to know, that, that inflated military ardour and love for brass buttons and gold lace, which so attracts the variety of younge men, broke out with violence of a prairie fire in many places in the State, and none more so than Henderson. January 15th of this year, a company of State Guards was organized in Henderson, with Wm. P. Fisher, an old soldier of the Mexican Way, and a man of handsome appearance and military bearing, Captain; Hon. Ed. G. Hall, First Lieutenant, and Hon. Robert T. Glass, Second Lieutenant. Colonel Holloway, who was now twenty-five years of age, found his first opportunity to indulge his military taste, and was one among the first to enroll his name as member of this company. In a very short time the company was regularly equipped with splendid guns and accoutrements and uniformed in cadet gray.

IN the fall of 1860, owing to some irregularity, Captain W. P. Fisher resigned his office, whereupon at a company meeting First Lieutenant Ed. G. Hall was promoted to First Lieutenant, and the subject of this sketch elected Second Lieutenant. From the beginning there was a secret dissatisfaction manifest in the company and, ultimately, and not a very long time after its organization, upon the second election, a large number of the men in line resigned. In the early spring of 1861 it was apparent to all thinking men, that the breach between the North and South could not be healed, and that war was to be the inevitable result. Then it was that a division of opinion manifested itself on unmistakable utterances in the rank and file of the Henderson company. Some denied the right of the Federal Government to call upon Kentucky for her enrolled soldiery to aid in suppressing the rebellion brought on by the Confederate States, while others accorded to the Government that right. Lieutenant Holloway was among the latter number who believed in the Governor's right to suppress the Rebellion, and if necessary to that end, to call upon Kentucky for her enrolled militia, in order to hold the Union of States in tact. He believed the South should seek redress for her grievances (if she had any) in the Union and not out of it by the force of arms. This division of sentiment grew stronger day by day, when a number of those who held loyalty to the Government finding themselves outnumbered, withdrew from the company. Lieutenant Holloway tendered his resignation as third officer of the company, and, on the eleventh day of June, 1861, the same was accepted by General Simon Bolivar Buckner. Immediately upon the reception of his resignation, Lieutenant Holloway commenced recruiting what was then styled a "Home Guard" company, and so successful was he that, on the twenty-fourth day of June, only thirteen days, a company with a full complement of men was organized, with James H. Holloway as Captain; Louis W. Danforth, First Lieutenant; William R. Lancaster, Second Lieutenant, and Andy Rowdin, Third Lieutenant.

At that time there was great difficulty in procuring arms from the State. A great many people of Kentucky believed that there was a secret determination on the part of the Governor and other Kentucky officials to place the arms in possession of the State in some way, so that they could be seized at the proper time by the Confederates, and not let them cut to what was vulgarly styled the "Home Guards," a recognized Union organization. be this as it may, the writer was detailed, and appointed to visit the Governor, not in the interest of Captain Holloway's company particularly, but to secure arms for a company organized prior to Holloway's. Arriving at Frankfort, an early interview was had with his excellency and others, and the matter brought to their attention. Ludicrous as it may seem, this delegate was informed that in order to protect the arms of the State from seizure by the Confederate authorities, they had all been safely packed and shipped to Paducah for safe keeping; but, if there was a sufficiency to equip two companies, and no requisitions held precedence, then the arms would be issued to the Henderson companies. Subsequently a requisition was issued to the officer in charge at Paducah, to deliver what arms Henderson had applied for, and as soon as possible after this, Mr. William S. Johnson, a member of the company organized prior to the one commanded by Captain Holloway, was detailed to go to Paducah, present the requisition and return with the arms. Upon his arrival, he found to his astonishment that the State arms had been removed to Mayfield, in the interior of the State, and the heart of rebeldom "for safe keeping." He proceeded to Mayfield, and there learned that only a few days before Kentucky's arms sent for safe keeping had simply passed through the town on to Dixie's land. It was the day of the first battle of "Bull Run," and this place selected too, as a safe repository for the arms of the State, was politically as hot as a pepper box with all of the heat on the sunny side. It was so warm that a "Home Guard" took his medicine with ice in it, and thus kept cool. Mr. Johnson returned without any arms. Captain Holloway determined not to be outdone, and, through his indomitable energy, a full complement of guns and accoutrements were obtained from General Lovell H. Rouseau, then recruiting a regiment for the Government service at Jeffersonville, Indiana. Captain Holloway drilled his company on the streets of Henderson night after night. His men being un-uniformed, presented a sorry appearance to the glittering epauletted squad of the Buckner State Guards. September 20th, 1861, he received, through General James S. Jackson, who was then recruiting a regiment of cavalry at Owensboro, from the State Military Board at Frankfort, an order to proceed with fifty men to lock and dam No. 1 at Spottsville, on Green River, and protect the same, the order stating that lock Nos. 3 and 4 had been destroyed, and Nos. 1 and 2 were threatened. In obedience to this order he, with a detail of about forty men of his own company, and Company "A," Lieutenant Charles T. Starling, commanding, left Henderson late in the afternoon, marching over rough roads through a heavy sleet and rain, arriving at the lock about ten o'clock in the night. Here the command remained until October 5th, 1861, when it was relieved by a detachment of Federal troops sent up from Evansville. Captain Holloway returned to Henderson and commenced recruiting a company for the Federal service. On the fifteenth day of October, he established Camp Holloway, on the grounds of the Henderson Fair Company, where General James M. Shackelford and General Ben. H. Bristow were engaged recruiting the Twenty-fifth Kentucky Infantry Regiment. On November the twenty-fifth, 1861, Captain Holloway and company were regularly mustered into the United States service at Ashbysburg, on Green River. The company was mustered into the Twenty-fifth Regiment was assigned to General Thomas L. Crittenden's division, then organizing at Calhoon, on Green River, and brigaded under the command of Colonel Charles Cruft, of the Thirty-first Indiana Regiment, acting Brigadier General.

On the second of December, 1861, the Twenty-fifth Regiment was attached to General Thomas L. Crittenden's Division, then at Calboun, on Green River, and assigned to General Charles Cruft's Brigade. On the ninth day of February, 1862, General Cruft, under orders, embarked his division on board a fleet of transports and proceeded down Green and the Ohio Rivers to Paducah, where he received orders to proceed to Fort Henry, on the Tennessee River. Arriving there, it was soon found that the fort had surrendered to General Grant. General Cruft was then directed to return to Paducah, which he immediately did, and there received orders to proceed to Fort Donnelson and reinforce Grant. The brigade was hurried up Cumberland River and disembarked a few miles below the fort and assigned to General Lew Wallace's Divison. Captain Holloway and his company fought nobly at the battle of Donelson and, to his credit, be it said, made the regimental report of the part taken by the regiment to his Brigade Commander. He was then sent to Fort Henry, and from thence to Shiloh, where he was taken ill with typhoid fever, and returned home under sick furlough. During his illness, the great battle of Shiloh was fought, and after the fight his regiment was consolidated with the Seventeenth Kentucky, Colonel John H. McHenry, commanding. Captain Holloway, although offered promotion, declined and tendered his resignation, which was accepted. At Donelson, Cyrus Steele, a brother of Captain O. B. Steele, of the Confederate Army, and who was engaged in the same fight, was mortally wounded. Lieutenant John G. Holloway was also severely wounded--in fact, his company and regiment were literally cut to pieces. On the twenty-sixth day of July, 1862, Captain Holloway received a commission as First Major of the Eighth Kentucky Cavalry, then organizing at Henderson by Colonel James M Shackelford and Lieutenant Colonel Benjamin H. Bristow. Twenty days afterwards, Major Holloway had in camp nine hundred men, when he received orders to recruit no more, and to consolidate his men into companies of one hundred and four men each. During this time he was constantly engaged in scouting the country and was engaged a number of times with the rebels. It was upon one of his raids into Union County that Owen Glass, a Confederate and native of Henderson, was killed. He frequently met in combat, his old friend and school mate, Colonel Adam Johnson; his old friend and one time commander, Colonel Ed. G. Hall, and Bob Martin, whose name was a terror throughout the country. On November 4th, 1862, he was ordered with his command, to Bowling Green. This trip he made overland, and, at Summer's store, in McLean County, was attacked by Captain Fowler's company, of Johnson's Command. Fowler was repulsed by Lieutenant Peter P. Brown, now if Cairo, and Fowler killed.

Major Holloway was then actively engaged in scouring the country from Russellville to the Cumberland River, where he removed an immense pile of rock from the channel of the river that had been placed there by the Confederates. He was, for a long time, engaged in gathering and forwarding supplies to Rosencranz's Army, at Nashville. On the first day of May, 1863, Major Holloway was mustered in as Lieutenant Colonel of the Eighth Kentucky, to date from January 1st, 1863. June 27th he was ordered forward to Burksville, to intercept General John H. Morgan, who was at that time moving into Kentucky. Morgan had crossed the river ahead of him, and then it was a whip and spur race to the Ohio at Brandenburg, where Morgan crossed into Indiana. Major Holloway was along in all of that terrible chase. At Buffington's Island he overtook and charged a portion of Morgan's men, capturing three hundred and ninety seven prisoners. After several days spent in the locality of Buffington Island, his regiment was ordered back to Russellville, via Louisville.

The chase after Morgan was a terrible one, the soldiers remaining in their saddles most of the time from June 27th to July 22d. September 23d, Colonel Holloway's term of enlistment having expired, he was mustered out of the service, and, although tendered a regiment, respectfully declined the offer. After being mustered out, he remained with his cousin, Lieutenant John G. Holloway, who was suffering from an aggravated attack of typhoid fever, and from which he died on the twenty-seventh day of September, 1863.

April 19th, 1864, Colonel Holloway married, in Fayette County, Miss Mollie E. Williams, the accomplished daughter of General John S. Williams, of the Confederate Army, and who, in the War with Mexico, earned the sobriquet of "Cerro Gordo," for distinguished services, in storming and capturing the Mexican heights bearing that name. General Williams served as United States Senator from Kentucky.

Mrs. Holloway was born in Clark County, July 24th, 1843, and is the mother of five children, Mary Ann Holloway, born in Henderson; Pattie Harrison, Lizzie Hillyer, John Williams and James Hillyer Holloway, born in Clark County. Here the Colonel has followed farming, raising Shorthorn and high grade cattle, horses, mules, and other stock, besides cultivating all of the cereals and hemp until January, 1878, when he removed to Winchester, the county seat, and engaged in the general grocery and hardware business, and has so continued up to the present time. He has frequently been importuned to offer for political office, but has steadfastly declined, preferring the peace and comforts of the home circle to the turbulent uncertainties and vexations of official political life. Since 1868 he had held the honorable position of Elder in the Presbyterian Church. He is also, at this time, President of the Clark & Bourbon Turnpike Road Company; a member of the Winchester City Council; a director of the Grange Mutual Benefit Insurance Company, Georgetown, Kentucky. The Colonel is greatly esteemed by all who know him, and he enjoys life with his charming wife and family to its fullest latitude.

The History of Henderson County, Kentucky by Starling 1887 page 742-49;

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