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High-stakes gamesmanship put Confederate and Union POWs on notice for execution following the Battle of Brandy Station.

CAPTAIN HENRY W. Sawyer spurred his horse forward, leading Company K of the 1st New Jersey Cavalry into the melee with Major General J.E.B. Stuart’s vaunted cavaliers on Fleetwood Hill at the June 9, 1863, Battle of Brandy Station. Sawyer wasn’t in the fight for long. A bullet passed through his thigh, and another round struck his right cheek and then passed out the back of his neck. Despite his wounds, Sawyer, a powerfully built carpenter from Pennsylvania, remained in the saddle until his horse was shot, pitching him to the ground. When he regained consciousness, killed and wounded cavalrymen were lying all around him. Among the dead were Lieutenant Colonel Virgil Brodrick, the 1st New Jersey’s commanding officer, and battalion commander Major John H. Shellmire. After two Rebels took the captain prisoner, his wounds were treated at a house in nearby Culpeper. He later recovered sufficiently to be transported to Richmond’s notorious Libby Prison. There Sawyer found himself at the center of a drama that had begun in Kentucky two months earlier—and would come close to ending his life.

On April 9, 1863, Federals had arrested Confederate Captains William F. Corbin and T.G. McGraw near Rouse’s Mills, Ky. Major General Ambrose E. Burnside, commander of the Department of the Ohio, convened a military commission that convicted the men of spying and recruiting within Federal lines. On May 15, Corbin and McGraw were executed at the prisoner of war camp at Johnson’s Island on Lake Erie, near Sandusky, Ohio.

When Colonel Robert Ould, the Confederate agent for the exchange of POWs, learned of those executions, he notified his Union counterpart, Lt. Col. William H. Ludlow, that two Union captains in Southern custody would be selected for retaliatory execution. On May 25, Ludlow informed Ould that Captains Corbin and McGraw had been executed as spies, and “that if he proposed to select brave and honorable officers who had been captured in fair open fight on the battlefield” the Union Army would select two more men to execute, continuing the bloodshed. Confederate President Jefferson Davis intervened to stay the execution.

The matter of retaliatory executions was reopened, however, when Rebel Brig. Gen. John H. Winder, who commanded the Department of Henrico, Va., issued Special Orders No. 160 on July 6, 1863, ordering Captain Thomas P. Turner, Libby Prison commandant, to select by lot two captains to be shot in retaliation for the deaths of Corbin and McGraw. Turner summoned the 75 captains in the prison. The Richmond Daily Whig reported, “When the Captains were first ordered to proceed to a lower room, they were in high glee, thinking, doubtless, that they were to be sent off by the flag of truce that goes today; but their joy received an instantaneous check when they heard the order of General Winder read.”

Turner had the men formed into a hollow square around a table. The names of all the captains were written on slips of paper, folded up and placed in a box. The prisoners were then told that the first two men whose names were drawn would be shot. Reverend Joseph T. Brown of the 6th Maryland Infantry drew the first name— Henry Sawyer. Captain John M. Flinn of the 51st Indiana Infantry, the second man selected, had been captured by Brig. Gen. Nathan B. Forrest when his brigade, mounted on mules, had conducted an ill-fated raid in northern Alabama in April. Sawyer showed little emotion during the name-drawing, according to the Whig, but Flinn was “very white and depressed.”

Sawyer and Flinn were taken to General Winder’s headquarters. The historian of the 51st Indiana later claimed that Winder “shamefully cursed and abused them, and [told them] that they would be executed within ten days.” He then ordered them to the dungeon, telling them that they would wait for their sentences to be carried out in solitary confinement.

Sawyer thought that if he could bring his plight to the attention of the Federal government, something might be done to save his life. He penned a lengthy letter to his wife on July 6, explaining that he was resigned to his fate, but also entreating her to visit him: “I cannot think of dying without seeing you and the children….My dear wife, the fortune of war has put me in this position. If I must die, a sacrifice to my country, with God’s will I must submit; only let me see you once more….I wish the ball that passed through my head in the last battle would have done its work; but it was not to be so.”

Sawyer and Flinn were held in a dank dungeon that measured about 6 feet wide, and fed only cornbread and water. The sentry who stood in front of their cell was to challenge them once every half hour and receive a reply via a small hole in the door—so it was impossible for both men to sleep at one time. Sleep was difficult anyway, due to the rats that shared their cell.

On July 11, the two prisoners penned a letter to Winder, pleading for their lives: “No crime is charged against us, nor have we been guilty of any. It seems our lives are demanded as a measure of retaliation on our Government for the execution of two persons in Burnside’s department of our army….” They concluded by pleading, “Innocent as we are of any offense against the rules of war, in the name of humanity we ask you if our lives are to be exacted for the alleged offense of other men in other departments of the army than that in which we served?”

Colonel Ludlow, meanwhile, was trying to save Sawyer and Flinn by selecting two Confederate officers “for execution in retaliation for the threatened one of Sawyer and Flinn.” Ludlow had two officers in mind: Brig. Gen. William H.F. “Rooney” Lee, Robert E. Lee’s son, and Captain William S. Winder, the son of General John H. Winder.

Sawyer’s wife also pleaded their case directly to President Abraham Lincoln, visiting him with a friend, Captain W. Whelden, and New Jersey Representative John T. Nixon on July 14.

Lincoln ordered General in Chief Henry W. Halleck to have Ludlow “place General W.H.F. Lee and another officer selected by you not below the rank of captain, prisoners of war, in close confinement and under strong guard,” and to notify Ould that if Sawyer or Flinn, or “any other officers or men in the service of the United States not guilty of crimes punishable with death by the laws of war, shall be executed by the enemy, the aforementioned prisoners will be immediately hung in retaliation.”

Rooney Lee, like Sawyer, had received two wounds at Brandy Station, a saber cut and, far more serious, a gunshot wound to the leg that narrowly missed the tibia and main artery. The brigadier general had been taken to the home of his father-in-law, Colonel Williams Wickham of the 4th Virginia Cavalry, in Hanover County to recuperate. A force of more than 1,000 Federal cavalrymen captured Lee there on June 26.

Ludlow had Rooney Lee placed in close confinement in a Fort Monroe dungeon with Captains Winder and 26-year-old Robert H.

Tyler of the 8th Virginia Infantry, who had been incarcerated in the Old Capitol Prison in Washington, D.C. Echoing Sawyer and Flinn’s ordeal, Tyler’s fate was sealed after lots were drawn; Tyler joined Lee in Fort Monroe’s dungeon the following day. As for Captain Winder, the Federals apparently changed their minds about executing him, opting for Tyler instead because they surmised he was a higher-profile target, believing he was related to former President John Tyler.

Tyler, a farmer from Prince William County, Va., was married to Sallie Sophia Chinn Tyler, whose father owned a substantial portion of the land upon which the First and Second Battles of Bull Run had been fought. Although Tyler was not related to former President Tyler, his father, William Bailey Tyler, was actually a second cousin of President James Monroe—though Federal authorities had no way of knowing that.

Tyler had moved to Memphis, Tenn., at 18, becoming a teacher at Armstrong’s Academy. During the secession crisis he returned home to Prince William County and helped his friend, Captain Edmund Berkeley, raise Company C of the 8th Virginia Infantry. Tyler fought bravely in several battles, playing such a conspicuous role in the October 1861 Battle of Ball’s Bluff, for example, that Berkeley wrote, “No more gallant officer served during the war or one who performed his duty more cheerfully and faithfully than Capt. Robert H. Tyler.” Tyler had been at home on leave when he was captured in May 1863.

Colonel Ludlow informed Ould what had occurred, and what the U.S. government’s new policy would be regarding retaliatory executions. A Union officer later commented that the Federal high command had rightly surmised “that the influential connection of these two officers in the Confederacy would prevent the threatened execution of the Union captains who had drawn their death warrants in the dreadful lottery in which they had been compelled to take tickets.”

For Lee and Tyler, waiting to hear what their fate would be, it was a harrowing time. “For weeks they lived in hourly expectation of being led out to execution,” wrote Tyler’s former commander, Berkeley, “and when any noise was heard outside their cell they thought it was the guards coming for them. So trying was this on them that although Captain Tyler weighed when taken prisoner 160 pounds, he only weighed 120 pounds when liberated having lost exactly one-fourth of his weight.” Tyler later recalled in an 1886 letter to Henry Sawyer: “Oh, Captain, that was a dread ordeal through which we passed. It is so impressed on me, that cold chills creep over me, while I recall it. I have thought of you thousands of times, in connection with it. As soon as I reached Richmond I went to the Libby and inquired for the cell, in which Flynn [sic] and yourself were placed. I could enter fully into your mental sufferings while there.”

The final player to enter the Libby Prison drama, Brig. Gen. Neal Dow of Maine, was a 59-year-old fire-and-brimstone supporter of temperance and abolition, who had been sent to Libby Prison in May 1863 after he was wounded and captured at the Battle of Port Hudson. The highest-ranking Union officer then in captivity at Libby, Dow would receive special attention from Confederate authorities due to his rank.

Shortly after arriving at Libby, Dow met Captains Sawyer and Flinn. “When I met them they were naturally very depressed by what they believed to be their impending fate,” Dow recalled, “but, with others, I did everything possible to rekindle their hope, assuring them that the Confederates would not dare to carry out their threat.”

Dow was a close friend of Vice President Hannibal Hamlin and several influential senators, who he contacted hoping they could arrange for a prisoner exchange. Ultimately their efforts would succeed, but the wheels of bureaucracy turned very slowly.

Flinn and Sawyer remained in the dungeon until August 16, 1863, when they were allowed to rejoin the general prisoner population. But the Richmond newspapers were still anticipating that the two Yankee captains would be executed. The Philadelphia Inquirer later reported, “About the 10th of August the prisoners were removed from this vault to the upper rooms among the other prisoners, where 1100 men were confined in six rooms, averaging about 37 by 100 feet each.” Relieved, Ludlow wrote on August 20, 1863, “I am satisfied, as I have been from the first, that Sawyer and Flinn will not be executed. This was settled by the prompt and significant selections of Lee and Winder.”

That fall Tyler wrote to Colonel Ould to complain that Colonel William Hoffman, the Union officer who was in charge of POW camps, was still holding him in close confinement as of October 8, 1863:

Colonel: On the 16th of July I was taken from our Confederate officers in the Old Capitol and placed in close confinement, as Superintendent Wood supposed, as a hostage for Captains Sawyer and Flinn. Since the release of Sawyer and Flinn from close confinement, Mr. Wood has endeavored to have me released, but Colonel Hoffman, Commissary-General of Prisoners, will not order my release, nor will he state why or for what purpose I am still held in close confinement. The superintendent is unable to find out why I am held. I was placed in close confinement the same day that General Lee and Captain Winder were, and it was believed by all the officers of the prison that I was a hostage for Sawyer and Flinn. I would be extremely obliged to you if you represent my case to [Brig. Gen. Solomon Meredith, who has replaced Ludlow as Federal commissioner], and have me exchanged when our officers are and placed on the same footing with them until an arrangement for an exchange is effected. I am extremely anxious to know why I am held. Superintendent Wood has tried in vain to find out. I trust you will attend to my case at your earliest convenience.

On December 15, Hoffman ordered that Tyler be treated like any other prisoner, and the Virginia captain was at last released from close confinement.

On November 13, Rooney Lee had been transferred to Fort Lafayette, located on an island in New York Harbor. Tyler joined him a month later. In the interim, Lee had his own trials. His wife Charlotte, always in fragile health, became desperately ill a few days before Christmas and died on December 26. Rooney’s mother, Mary Lee, had the unhappy task of informing her son that he was now a widower.

General Dow finally learned through an unidentified Confederate officer who visited him that Ould supported the idea of a prisoner exchange. The same officer suggested that Dow should point out that the U.S. government had made the proposition, and the Confederate authorities would agree—but the Rebel warned Dow that the Southern authorities would not take the initiative in the effort. On January 28, 1864, Dow composed two letters to his son, one written in ink and the other a secret missive penned in lemon juice on the back of the paper. In the letter in ink he wrote:

I have reason to believe that if the government will propose to exchange General Lee for myself, the only Federal general here, and equivalent officers for Captains Sawyer and Flynn [sic], who were selected by lot for execution in retaliation for the execution by Burnside of two officers alleged to be recruiting within his lines in Kentucky for the Confederate service, the proposition will be favorably entertained and the exchange effected. General Lee was captured at a private house, sick, as I was at a private house, wounded.

If our friend [Charles A. Stackpole, of Portland] will kindly consent, the best thing will be for him to go immediately to Washington and see my friends there. There should be no delay about it. I have no reason to doubt that the government will consent to the measure, since no question of public policy is involved in it. Several special exchanges have already been effected.

His secret message in lemon juice (which would become legible when the writing was exposed to heat) was as follows :

The information comes to me through the commissioner, Judge Ould. The Confederate government will not propose the exchange, as they refuse to exchange generally man for man and rank for rank. They will exchange me for General Lee, without regard to Sawyer and Flynn, but not them, leaving on our hands General Lee. Our government may possibly think it desirable to hold Lee. If so, I am content to remain. Our government must not yield a hair’s breadth in relation to the status of the negro in our armies and its duty to protect him in every respect as if he were the most honored white. To recede will be to forfeit honor and merit defeat. We should be utterly disgraced before the world.

Dow’s son and Stackpole went to Washington to see what could be done. With help from Vice President Hamlin and the two senators from Maine, the exchange was then put into motion.

Major General Ethan A. Hitchcock, who had replaced Solomon Meredith as the Union negotiator, wrote on February 8, 1864: “It has been intimated from Richmond that if we will consent to exchange General Lee and two officers of the grade of captain the rebel authorities will give us General Dow and Captains Sawyer and Flinn. If you can obtain the assent of the rebel authorities to this exchange, making sure that we shall receive Captains Sawyer and Flinn, the exchange can be made, and General Lee will be sent to you for the purpose.”

On February 23, 1864, Dow received letters from Hamlin and Senator Lott M. Morrill of Maine saying the U.S. government had proposed to exchange Rooney Lee for Dow. Tyler would be exchanged for Sawyer and Flinn. Lee and Tyler were sent back to Fort Monroe in anticipation of their exchange. Finally, on March 14, the exchange was completed, with the prisoners returning to their respective commands. Sawyer’s biographer, C.E. Godfrey, wrote: “The satisfaction with which Captain Sawyer once more walked forth a free man, and found shelter under the Old Flag, was such as only a man coming from death unto life— from dismal bondage into joyous and perfect liberty—can ever experience, and none other, certainly, can appreciate.”

Rooney Lee had been promoted to major general while in captivity, and after his release he assumed command of a division of cavalry created specifically for him. He ended the war at that rank. After the war, Lee became a gentleman farmer and involved himself in veterans affairs and politics. He was elected to the Virginia State Senate in 1875, then appointed the president of the state agricultural society in 1878. Beginning in 1887, he was elected to three terms in Congress, serving from 1888 until his death on October 15, 1891.

John Flinn never recovered from his time in Libby Prison. Already in ill health when he was liberated, he died at age 39, six months after his release.

Robert H. Tyler returned to the 8th Virginia Infantry, but he was captured by the enemy once again at the Battle of Sailor’s Creek on April 6, 1865, just three days before Robert E. Lee’s Army of Northern Virginia surrendered. “My reg’t, 8th Va. Inf., numbered only 80 men in the ten companies,” he wrote to Henry Sawyer in 1886. “We had fought the whole war through together, and I tell you ‘the Iron entered my soul when I had to surrender them’ I surrendered in good faith and I will stand by the ‘Old Flag,’ the red, white and blue, as devotedly as we followed that of ‘The Lost Cause,’ which will never be unfurled.” Tyler would later claim that “Sailors creek has so ruined me, that I have not even time to put anything on paper, wither for my own reference in after life or for the perusal of my boys but still I keep thinking and my conclusions are never favorable to the Yankees.”

In his second stint as a POW, Tyler was sent to Johnson’s Island. He was released after taking the oath of loyalty to the U.S. government on June 20, 1865, and then returned to his Virginia farm, known as “The Shelter.”

In 1871 he wrote, “The fact is that every moment of my time, has of necessity to be devoted toward building up income and support for my little brats and whenever I can find nothing to pay me better, I have of necessity to take the plough.” Tyler served two terms in the Virginia General Assembly’s House of Delegates, and also became a trustee of the Manassas Industrial School for Colored Youth. He died on January 23, 1902.

Neal Dow’s health was wrecked in prison, leaving him unfit for further duty in the field. In November 1863, he returned to Maine, where he resumed his temperance activism. In 1880 he ran for president on the Prohibition ticket, receiving 10,305 votes. He lived to 93, dying in Portland on October 2, 1897. Dow’s memoirs were published in 1898.

Henry Sawyer was promoted to major of the 1st New Jersey Cavalry on March 22, 1864, to date from October 12, 1863. He rejoined his regiment after leaving prison. By the time he received his honorable discharge on July 24, 1865, he had been wounded twice more, at the Second Battle of Kernstown in July 1864. After the war he was breveted a lieutenant colonel.

Secretary of War Edwin M. Stanton offered Sawyer a lieutenancy in the Regular Army at the war’s close, but Sawyer declined. He settled in Cape May, N.J., where he became active in local politics. He also owned a hotel and resort, the Chalfonte, that is still in business today. Sawyer died on October 16, 1893.

Through no fault of their own, the POWs profiled here had all become pawns in a much larger game during their incarceration. Fortunately none was hanged, and all but one man prospered in civilian life after the war.

Only the unfortunate John Flinn can be seen as a direct casualty of high-stakes gamesmanship engendered by sectional warfare. The Indiana captain’s jet-black hair had reportedly turned completely white within a day of his being condemned to death and thrown into Libby’s dungeon. For poor Flinn, memories of his seven weeks under the constant threat of execution could never be erased.


Eric J. Wittenberg is the author of The Battle of Brandy Station: North America’s Largest Cavalry Battle, among other books. He wishes to thank Ellie Ivancic for her assistance in finding additional information on Captain Robert H. Tyler.

Originally published in the August 2012 issue of Civil War Times. To subscribe, click here.