DS was the son of Susanna (Curfman) and William CALDWELL.
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Enlisted on August 16, 1862 as a private in Co. H, 123rd Ohio Volunteer Infantry Regiment, at the age of 41. He was appointed as a 1st Lieutenant on August 22, 1862. The regiment was mustered into the Federal Army on September 25, 1862, at Camp Monroeville, Huron Co., Ohio. He obtained promotion to captain on February 3, 1863.

The first major engagement for the 123rd Ohio was the second Battle of Winchester. The Union Army under Brigadier General Elliott engaged the Confederate forces under the command of General Jubal Early, who was in the process of moving north through the Shenandoah Valley to join up with Robert E. Lee for the invasion of Pennsylvania. The outcome was that the 123rd surrendered [except for Company D] and was sent to Richmond as prisoners of the Confederacy. The officers were incarcerated at Libby Prison at Richmond, Virginia on June 15, 1863. Capt CALDWELL was elected by the other prisoners to serve as unofficial chaplain.

The most famous prison of the Civil War was Libby Prison [as the officers called it RAT HELL], on the western half of a block bounded by Cary and Dock Streets at 20th. Colonel Thomas Ellwood ROSE and Major Andrew G. HAMILTON devised a plan calling for access to the basemment. After eight months of imprisonment, my GGGrandpa, DS CALDWELL, and at least two dozen Union POW officers worked in shifts digging through a tunnel in just 17 days. They used an old pocket knife, some chisels, a piece of rope, a rubber cloth and a wooden spittoon. On February 9, 1864, CALDWELL and 108 other officer POWs escaped to freedom through a shaft ending at a Richmond alley. 48 POWs were recaptured, including Col ROSE, and 2 drowned on the river – the remaining 59 made it to the Union lines. Many of the escapees managed to find the home of Elizabeth Van Lew, a Unionist spy in Virginia who was a regular visitor to the prisoners. She aided those who made it to the Union lines. D.S. CALDWELL rejoined his regiment on March 30, 1864. The regiment was present for the surrender on April 9, 1865.

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From the Richmond Examiner, 11 February 1864
ESCAPE OF ONE HUNDRED AND NINE COMMISSIONED YANKEE OFFICERS FROM THE LIBBY PRISON - A SCIENTIFIC TUNNEL - THEIR UNDERGROUND ROUTE TO LIBERTY. – One of those extraordinary escapades of prisoners of war which have been very frequent on both sides, occurred at the Libby Prison between the hours of darkness on Tuesday evening and daylight yesterday morning. The discovery was first made at the daily morning count, when the number of the prisoners fell alarmingly short. The roll was then resorted to, as it always is when the count does not correspond with the number booked. The calling of the roll consumed nearly four hours and out of the one thousand and fifty odd officers confined in the prison the day previous, one hundred and nine were found to be missing. At first it was suspicioned that the night sentinels had been bribed, and connived at the escape; and this suspicion received some credence from the statements of the Yankee officers, who said the guards had passed them out by their posts. The officer of the guard, and the sentinels on duty the night previous were accordingly placed under arrest by Major Turner, and after being searched for money or other evidences of their criminality, confined in Castle Thunder in order that further developments might either establish their innocence or fix their guilt upon them. In the meantime Lieutenant La Touche and Major Turner made a thorough inspection of the basement of the prison, which slopes downward from Cary street towards the river dock. This basement is very spacious and dark, and rarely opened except to receive commissary stores. A stairway leading down from the first floor, has long ago been boarded over and there was no communication from above. The wall masonry of the basement, near the front of the building, commences at least ten feet below the level of Cary street. At the base of the east wall, and about twenty feet from the Cary street front, was discovered a tunnel, the entrance to which was hidden by a large rock, which
fitted the aperture exactly. This stone, rolled away from the mouth of the sepulchre, revealed an avenue, which it was at once conjectured led to the outer world beyond. A small negro boy was sent into the tunnel on a tour of exploration, and by the time Major Turner and Lieutenant La Touche gained the outside of the building, a shout from the negro announced his arrival at the terminus if the subterranean route. Its passage lay directly beneath the tread of three sentinels, who walked the breadth of the east end of the prison, across a paved alley way, a distance of more than fifty feet, breaking up inside of the enclosure in the rear of Carr's warehouse. So nicely was the distance gauged, that the inside of the inclosure was struck precisely, which hints strongly of outside measurement and assistance. Through connection once opened, the prisoners were enabled to worm themselves through the tunnel, on by one, and emerging at least sixty feet distant from any sentinel post, to betake themselves off, singly, through an arched gateway, to some appointed rendezvous. To reach the entrance of the tunnel it was necessary for the prisoners to cut through the hospital room and the closed stairway leading into the basement. All the labour must have been performed at night, and all traces of the work accomplished at night was closed up or cleared away before the morning light. The tunnel itself is a work of several months, being about three feet in diameter and at least sixty feet in length, with carvatures worked around rock. Upon the testimony afforded by the revelation of the tunnel, the imprisoned guards were at once released and restored to duty, the manner of the escape being too evident.
The following is a list of the principal officers who escaped, and their rank. Among them we regret to have to class the notorious Straight.

Colonels: J.F. Boyd, Twentieth army crops; W.G. Ely, Eighteenth Connecticut; H.C. Hobart, Twenty-first Wisconsin; W.P. Kendrick, Third West Tennessee cavalry; W.B. McCreary, Twenty-first Michigan; Thomas E. Rose, Seventy-seventh Pennsylvania; J.P. Spofford, Ninety-seventh New York; C.W. Tilden, Sixteenth Maine; T. S. West, Twenty-fourth Wisconsin; A.D. Straight, Fifty-first Indiana; D. Miles, Seventy-ninth Pennsylvania.

Majors: J.P. Collins, Twenty-ninth Indiana; G.W. Fitzsimmons, Thirtieth Indiana; J.H. Hooper, Fifteenth Massachusetts; B.B. MacDonald, One Hundredth Ohio; A Von Witzel, Seventy-fourth Pennsylvania; J.N. Walker, seventy-third Indiana; J. Henry, Fifth Ohio.

There was Rev. Capt. D.S. Caldwell, besides thirty other captains and fifty-nine lieutenants, making one hundred and nine in all, who gained their liberty without the preliminaries of parole or exchange. Of this number four only had been returned to the prison up to last evening, re-captured. These were two captains and two lieutenants. Two were overtaken near Hanover Court House, and the others, about twenty miles below Richmond, on the Williamsburg route.

Couriers were early dispatched in every direction, and the pickets double posted on all the roads and bridges. It is quite evident that the escaping prisoners have scattered and are travelling singly or in pairs, or are laying up in the houses, or hiding-places, provided for by the disloyal element to be found in and about Richmond. Doubtless many will be re-captured, but we fear too many will escape for the credit of the Confederacy. We believe the largest number of them are yet in Richmond, and will seek to steal off one by one in various guises other than that of the Yankee. It is fortunate that the leak was discovered when it was, or the exodus would have been continued last night, and night after night, until there would have been no Yankees to guard.

Brigadier General Neal Dow did not attempt the passage of the tunnel, for the reason that he was afraid his strength would fail him in his flight to the embrace of Butler the Beast.
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After the Civil War he devoted himself entirely to his ministerial duties. He wrote a book about his Civil War imprisonment "Incidents of War and Southern Prison Life" by D. S. CALDWELL, 123rd Regiment Ohio Volunteer Infantry.