Dead Man Riding

Jonathan Prince Cilley was a Thomaston lawyer who joined the 1st Maine Cavalry Regiment in autumn 1861. Severely wounded by a Confederate cannonball during late May 1862, he returned to action later that year. Confederates made so many attempts to kill him that Cilley could be described as “Dead Man Riding.” He commanded the 1st Maine Cavalry late in the war and lived well into the 20th century. (Maine State Archives Photo)

So what could Jonathan Cilley do after catching a cannon ball?

Die? Yup — or so thought everyone back home in Thomaston.

Born on Dec. 29, 1835 to Jonathan Longfellow Cilley and his wife, Deborah, the boy who became a Maine cavalry officer graduated from Bowdoin College (’58) and gained admittance to the Knox County bar in 1860. With the middle name of Prince, he should have settled into a princely existence as a successful Midcoast attorney.

Then a war beckoned, and Cilley recruited troopers for Co. B, 1st Maine Cavalry Regiment in autumn 1861. Capt. Jonathan Cilley had an old score to settle.

Elected to the 25th Congress in 1836, Jonathan Longfellow Cilley lambasted Southern congressmen during a speech delivered in the House of Representatives. The highly offended Kentucky Rep. William J. Graves challenged Cilley to a duel and mortally wounded him on a Blandensburg, Md. dueling ground on Feb. 24, 1838. Cilley died later that day.

His son and namesake evidently promised revenge on anything Confederate when the 1st Maine Cavalry headed to Washington, D.C. in March 1862. Absolutely nothing would stop Jonathan Prince Cilley as he battled Confederates all over Virginia for the next 37 months.

As Lt. Col. Calvin Douty and five 1st Maine Cavalry companies retreated into Middletown, Va. on May 24, 1862, Confederate Brig. Gen. Turner Ashby, two artillery batteries, and about 300 Louisiana infantrymen — the vaunted Wheat’s Tigers — debouched onto high ground north of town. Confederate gunners soon opened fire.

Leading his Co. B troopers across an orchard where shot and shell screamed and crashed, Capt. Jonathan P. Cilley of Thomaston shouted encouragement to his nervous men.

Then Cilley “was struck by a shell which nearly severed his right arm, leaving only a partial connection of skin” and bone, Archibald Spalding informed Maine Gov. Israel Washburn. After the 1st Maine’s debacle at Middletown, Washburn had sent Spalding to investigate the circumstances.

The explosion hurled Cilley from his horse “in much the deliberate manner in which a squirrel falls to the ground when shot,” recalled trooper Edward Tobie, who later wrote “History of the First Maine Cavalry, 1861-165.” Lieutenant Frank Cutler and other troopers carried Cilley into a nearby house owned by John Wright, a Middletown businessman.

Assisted by Cilley’s orderly, Isaac Harris, Assistant Surgeon George Haley cared for Cilley, who awoke “two or three days later” to discover that he lay immobile “on a lounge … and that he could now and then hear the steps of a woman crossing the room,” Tobie wrote.

The woman, Mrs. Wright, helped care for Cilley, too, even after Confederate soldiers arrived at her home and informed Cilley, Haley, and Harris that they were prisoners of war.
Believing that Cilley would die, Haley implored Mrs. Wright to deliver the bad news. She demurred, so Harris told Cilley, “Captain, do you know that you are mortally wounded and cannot recover?”

“Thunder!” Cilley exclaimed, displaying a stubborn streak that would serve him well throughout the war. “I am not going to die. What do you mean?”

“The, the doctor told me so,” Harris responded.

“Well, the doctor doesn’t know as much about it as I do. I intend to see the war finished,” Cilley growled.

Equipped with “a common handsaw and a butcher knife,” a captured 1st Vermont Cavalry surgeon soon darkened the Wrights’ door and offered to amputate Cilley’s smashed arm because he “had not seen a single amputation performed,” Tobie noted. Cilley, who had by now learned that he was a brevet major, declined the offer.

Meanwhile, Spalding confirmed from eyewitnesses the terrible wound suffered by Cilley. Troopers described the captain as “mortally wounded,” according to Tobie, and Spalding reported to Washburn that Cilley had “died immediately after being taken prisoner.” His body now occupied a Virginia grave.

The obligatory obituary appeared in Maine newspapers. Reading one particular obit months later, Cilley could agree with Mark Twain that “reports of my death were premature.”

In fact, Jonathan Cilley was just getting started.

He spent almost three months convalescing in Middletown, where he received “motherly care and nursing” from Mrs. Wright, Tobie wrote. Afterwards “his comrades attributed his chivalrous esteem of the women of Virginia to Mrs. Wright’s kindness, as he was inclined to damn the men of that state.”

Repatriated to Union lines at Winchester, Cilley traveled to Washington, D.C. and obtained a medical leave so he could go home to recover. Itching to fight, he returned to Washington in December “with his wound still unhealed” and seeping, Tobie wrote.

Soon admitted to Armory Square Hospital in D.C., Cilley underwent serious — and recurring — surgery and remained hospitalized until April 1863. Among his nurses was Caroline Abigail Lazell, with whom Cilley “formed the acquaintance and won the friendship,” according to Tobie. Lazell became “the lady who, after the war,” married Jonathan Cilley.

Enduring several surgeries that collectively removed “more than forty pieces of bone … from his arm,” Cilley clamored for action after he was discharged from the hospital. He petitioned for reinstatement with the 1st Maine Cavalry — and got it on Aug. 1.

Dismounted troopers of the 1st Maine Cavalry Regiment skirmish with Confederate cavalry in central Virginia on June 19, 1863. A Union artillery battery is located atop the distant hill. (Library of Congress Photo)

By now a staff officer — majors did not command companies — Cilley became a “dead man riding” in late 1863 and early 1864, participating in multiple battles and skirmishes where Confederates tried to kill him as they had in the Shenandoah Valley.

They almost got lucky.

On May 28, 1864, the 1st Maine Cavalry deployed to support a Union artillery battery “keeping up a heavy fire” and “drawing a smart fire” from enemy cannons during the Battle of Haws Shop in Virginia, according to Tobie. Troopers and horses stood in long lines “watching the shell and shot strike the ground in their front” as the Confederate gunners zeroed in on “a tall chimney supported by a large brick oven — all that the war had left of some mansion.

“Shells never scream so fiercely or sound so wickedly as under those conditions,” Tobie recalled.

Just before the Maine boys were allowed to dismount, “a shell came bounding along the line from right to left, taking off the legs of three horses in its course, and rolling along directly under the horse rode by Maj. Cilley, just in rear of Co. I,” Tobie wrote. “There was a general shudder … by all who saw it, in anticipation of the explosion, for the fuse was smoking …”

Cilley likely shouted at his horse to “move” or “run” or “charge” or “do something,” but the animal “was so thoroughly frightened” by the sputtering cannonball that the horse “could not be induced by the most vigorous application of the spur to leave the dangerous locality,” Tobie wrote.

But the fuse burned out, and “the explosion resulted harmlessly” to Cilley and his horse, Tobie noted.

On June 2, several officers “were sitting on the ground, in shade of a small tree” behind breastworks erected earlier that day by Maine troopers involved in yet another fight, Tobie wrote. Claiming that Confederate artillery had the range, one officer stood up and walked away; “sure enough, a moment later a shell passed between the bodies of Col. Smith and Maj. Cilley” and convinced everyone to vacate the premises.

Then, during the savage fight at St. Mary’s Church on June 24, Cilley commanded the regiment’s left flank. Seeking a vantage point, he rode up an open knoll and “was surprised to find that I offered a fair target to the rebel line.” Cilley “became vexed, and began to cuss myself for such a foolish … manoeuvre (sic),” as bullets hummed “by my ears.”

He escaped harm, rejoined the regiment, and monitored its fighting withdrawal “until the enemy interfered with the motion of one of my legs … I took a rest by going to the rear, and about sunset enjoyed the hospitalities of Surg.[eon] Stevens,” Cilley recalled. An ambulance later evacuated him from the field hospital.

The Confederate bullet put Cilley out of action until Sept. 26, when he rejoined the 1st Maine Cavalry as a lieutenant colonel and as its commander. Cilley held that position until the war ended — and Confederate sharpshooters were not done with him yet.

During the knock-down brawl fought at Five Forks on March 31, 1865, “suddenly I heard and felt a bullet — whew! And it hurt,” Cilley recalled. “Oh! Ough! Confound it!

“Sergt. Major Tobie, seeing my contortions, hurried to me and asked: ‘Are you wounded, Colonel? Will you go to the rear?’

“My indignation burst out with: ‘D—n the rear, I am wounded in the — rear,” Cilley replied.

He rode the lines as his Maine troopers battled advancing Confederate infantry at Appomattox Court House early on April 9; the 1st Maine boys killed just hours before Lee threw in the towel were among the last Maine lads to die in action during the Civil War.

Breveted to brigadier general, Cilley brought the 1st Maine Cavalry home and married Caroline on Oct. 10, 1866. Cilley resumed his law practice and later served in the Maine Legislature; he and Caroline had two children, Jonathan and Grace, before Caroline died in April 1871.

Twenty-six years later, Cilley married Mary Butler — and outlived her, too. His health failing, the elderly widower moved to Alameda, Calif. to live with Grace and her husband.

There, on April 6, 1920, death claimed Jonathan Prince Cilley 55 years after Confederates gave up trying to do so. He lies buried in the Cilley Cemetery in Thomaston.

If you enjoy reading the adventures of Mainers caught up in the Civil War, be sure to like Maine at War on Facebook and get a copy of the new Maine at War Volume 1: Bladensburg to Sharpsburg, available online at Amazon and all major book retailers, including Books-A-Million and Barnes & Noble


Brian Swartz can be reached at

Brian Swartz

About Brian Swartz

Welcome to "Maine at War," the blog about the roles played by Maine and her sons and daughters in the Civil War. I am a Civil War buff and a newspaper editor recently retired from the Bangor Daily News. Maine sent hero upon hero — soldiers, nurses, sailors, chaplains, physicians — south to preserve their country in the 1860s. “Maine at War” introduces these heroes and heroines, who, for the most part, upheld the state's honor during that terrible conflict. We tour the battlefields where they fought, and we learn about the Civil War by focusing on Maine’s involvement with it. Be prepared: As I discover to this very day, the facts taught in American classrooms don’t always jibe with Civil War reality. I can be reached at