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For more than two years, George St. Leger Grenfel did everything he could to get out of prison legally. His lawyer barraged federal officials with arguments assailing his conviction and his sentencing to life in prison. Friends testified to his impeccable character. Diplomats from his native England put pressure on President Andrew Johnson to grant executive clemency. But time and time again, the appeals were rejected. The tall, 68-year-old former Confederate colonel with the long white hair remained a prisoner in the worst prison the United States could offer: Fort Jefferson, off Florida’s Gulf Coast.

Grenfel accepted the rejections stoically, like the lifelong soldier he was. But then something happened that gave him new hope that he would soon be set free. For three months in late 1867, he helped tend some 300 prisoners and guards at the prison who were stricken with potentially fatal yellow fever. Even the prison commandant and the U.S. Surgeon General’s office urged President Johnson to send Grenfel home. It was just a matter of time, he thought, before he would be on his way to England.

Then came the response from Washington, D.C. It was a terse letter written by order of the president. Its message was as quick and certain as a gunshot: “Your application for clemency has been denied.”

Reeling from this devastating blow, Grenfel decided he had only two choices: wither away in prison or escape. He chose the latter. On a stormy March 7, 1868, he and his cellmate, Johnny Adare, slid down a rope along the outside of the prison wall. For some unknown reason, a prison guard joined the two fleeing inmates, and the three men ran through a slicing wind and stinging downpour to a small fishing boat. Before they shoved off, two more inmates, one still chained to a heavy iron ball, joined in the escape.

The five men struggled to launch the boat into the boiling surf. Somehow they managed to shove off and row out into the Gulf of Mexico through the heavy rain and choppy water. And with that, Grenfel and his accomplices disappeared, never to be seen again.

For most people, it would have been an unfathomable way to go. But for Grenfel, it was a fitting end to a life of adventure. For 50 years he had traveled the globe in search of action, and he had found more than his share.

Grenfel embarked on his life of adventure in 1817, when he left England at age 17 to join the French Chasseurs d’Affrique and fight in the deserts of northwest Africa. Before moving on, he slashed and shot his way through four tribal wars and revolutions. Later, he received a commission from the British governor of Gibraltar to finish off pirates in Morocco. “He cleaned them out of this world,” wrote one of his friends. In true soldier-of-fortune fashion, Grenfel served in South America as a colonel in Italian hero Giuseppe Garibaldi’s South American legion. He eventually tired of the non-stop adventure and returned home to England.

The glory of war, however, soon called like a siren, luring this fated warrior back into action. First he joined the British army and fought in the Crimean War in 1854. Then he went to India in 1857 to help put down the Sepoy Rebellion, an armed revolt against British rule. By this time he was in his late 50s. The idea of sitting in a comfortable chair, warming his feet by the fireplace, sounded good to him.

But that was before the American Civil War. His perspective changed when the New World went to war with itself. Again, Grenfel heard the siren call. He left England and sailed through the Union blockade to Richmond, Virginia. In meetings there, he talked Confederate officials into sending him to Tennessee to join Brigadier General John Hunt Morgan’s cavalry. As a former leader of marauding tribes in the Moroccan desert, he convinced the officials he had much to teach Morgan’s men about guerrilla tactics and military discipline.

Grenfel arrived in the Volunteer State in June 1862. There he met Captain Thomas Hines, an astonishing young cavalry officer. Hines developed an admiration for Grenfel and probably learned cavalry tactics from him. In no time, the two men became friends.

Hines was one of Morgan’s ablest raiders. He went on to lead successful raids in Kentucky and Tennessee, his troops appearing out of a morning mist, burning and looting, and then riding away. In between these actions, he often disappeared into Union territory to make secret contacts with the underground anti-Union groups whose members were known as “Copperheads.” He was preparing the way for a revolt behind Northern lines.

Grenfel, at 63 years of age, was too old for active raiding. He stayed mostly in camp, training Morgan’s officers and troopers. Fortunately for him, he stayed behind in Tennessee in July 1863, when Morgan’s raiders went on their infamous 24-day ride through southern Indiana and Ohio. Union cavalry units chased Morgan’s exhausted men for more than 900 miles. Most of them were captured and thrown into prisoner-of-war camps in Indiana and Illinois, but Morgan and his officers were locked up in the Ohio Penitentiary in Columbus, Ohio. In late November, Morgan, Hines, and six other Confederate officers made a daring escape through a tunnel they had dug under the brick prison. Bold as brass, they climbed aboard a train for Cincinnati and returned to the South.

Morgan resumed his old command, but Hines traveled with Grenfel to Richmond to talk with President Jefferson Davis about plans for a Rebel uprising in the North. Hines remained in the capital city for much of the winter. It turned out that his excellent record as a bold cavalry officer and long experience as a secret contact man with Copperhead groups made him a logical choice for an important new assignment: to organize a major military uprising in states north of the Ohio River. The goal of the clandestine operation, later known as the Northwest Conspiracy, was to pull the Union apart piece by piece, forcing the Federal government to negotiate an end to the war. In April 1864, Hines slipped north through Union lines and into Canada, where he joined Rebel conspirators in Toronto.

Meanwhile, Grenfel wrote from Richmond to his daughter in London that he was going to resign his commission. No doubt he was feeling his age. He planned to sell his horse and other goods and return to England. Something changed his mind, though, and he returned to work as Morgan’s adjutant general. But on September 4, Morgan was shot and killed in a surprise Union cavalry attack at Greeneville, Tennessee. Grenfel was out of a job, and he again made plans to retire to England. Again, however, he changed his mind, deciding to join Hines and other Rebel operatives working north of the Mason-Dixon Line.

Grenfel ran the Union blockade to Bermuda and caught a ship to New York City. There, he went to see Major General John A. Dix, commander of the Department of the East, at Fort Lafayette. He told Dix he was no longer associated with the Confederacy. Receiving Dix’s blessing, he took a train to Washington and got an interview with Secretary of War Edwin Stanton in June 1864. They talked about the Confederate military, and Grenfel offered some false figures for the army’s manpower. He closed by saying he was finished with the Confederacy and by promising to remain neutral in the war. With that, he persuaded Stanton to give him a pass to travel through the North. He then took Stanton’s safe conduct and hot-footed it off to Canada to join the secret Confederate plotters there. But deceiving Stanton would have terrible consequences.

Before plunging into his new line of work, Grenfel set aside a few weeks to rest. “Two years and a half of excitement and hard work have told on me,” he wrote in a letter to his daughter in London. “I shall rusticate a month or so–I hope–before I again get into the saddle….”

When Grenfel caught up with Hines, he stepped right into place as one of his commander’s trusted subordinates. The two men frequently traveled together, including on trips to Niagara Falls for conferences. “…We are now on the eve of great events…,” Grenfel wrote to associates in England. “The Northwest is ready for revolt…. I have not heard from all of you in a long time; I was going to say from home, but I forget I have no home….” Included in this mailing were detailed instructions for disposing of his estate after his death.

As the Northwest Conspiracy shifted into high gear, the Confederate conspirators in Canada planned a string of surprise raids in Northern cities. The grandest of these schemes was an intricate operation to free thousands of Confederate prisoners from detention camps in Indiana and Illinois. Grenfel found himself at the core of the ambitious plot. He traveled to Chicago during the Democratic National Convention in August 1864 and met Hines in the city. Hines had spent the past few weeks in disguise in Indiana and Illinois, planning the prison breaks with leaders of the Sons of Liberty and other Copperhead groups. The leaders were in Chicago with thousands of their supporters, all presumably ready for action.

As the zero hour approached, the Copperhead leaders lost their nerve–despite savage urging by Hines, Grenfel, and others. One of the Confederates blew the whistle on the secret operation to Colonel B.J. Sweet, the Union commandant at Camp Douglas, near Chicago, where 5,000 Confederates were imprisoned. At Sweet’s request, 3,000 additional Federal troops were sent to the city, and the Confederates’ months of careful preparation went for naught. Federal troops arrested and imprisoned many of the Copperhead leaders. The prospect for further action seemed dim.

Hines was not yet ready to abandon the plan, however. Only 24 years old and full of fire, he refused to accept the fact that the Copperhead leaders were not military leaders but merely bombastic politicians, and that their so-called army was an undisciplined, aimless mob. He gathered together the shreds of the conspiracy and rescheduled the uprising. He chose November 8, 1864, national election day, a day when everyone would be preoccupied.

Grenfel was assigned to Carlyle, Illinois, “to drill the Copperheads,” but he was completely discouraged. The great events he had anticipated failed to materialize. He was living in a small city that was “a hovel of hogs and Hoosiers.” His letters to his daughter revealed his gloomy disposition. He was so downhearted that he even contemplated his own death. “It does not matter much; we all have got to live a certain time and when the time comes,” he wrote to his daughter. “What difference will it make whether I lived in London or Illinois? And whether I died in a four-post bed or whether I died in a ditch…?”

Perhaps Grenfel was heartened when he received a new assignment in October to gather information for the prison raid. Registered under his own name at the Richmond House in Chicago, he posed as a hunter, complete with shotgun and dog. Ostensibly hunting for birds, he gathered intelligence with an eye to how the camp might be taken. “The hunting was good,” he wrote to Hines.

In early November, Hines and other Rebel officers crossed the Canadian border and headed for Illinois, confident that this time there would actually be a revolt and the prisoners would be freed. Charles “General” Walsh, a Copperhead leader, had assured Hines of this. The Copperheads had large caches of arms hidden near the prison camp. They claimed nothing had been left to chance.

Again, however, word of the plot preceded the Confederates to their target. The Federal Secret Service had heard more than a hint of the conspiracy from Felix Stidger, an undercover agent working inside the Indiana Copperhead hierarchy. Security among the Confederate officers was far from perfect. At a boisterous party in Chicago, one of them had talked to an old friend about the abortive raid attempt on Camp Douglas. Another conspirator, his tongue loosened by peach brandy, mentioned the names and whereabouts of some of the raiders to a friend. This friend proved to be a turncoat Confederate officer who immediately informed Federal army officers about the plot. Patrols were sent out, and the conspirators were arrested.

Grenfel was the first man caught. Northern troops took him during the dark, early-morning hours of November 7. His cover had been perfect–a British aristocrat out hunting birds, a dog at his heels–and, indeed, his movements had not attracted undue attention. But a Union patrol found out where he was staying, picked him up at his hotel, put leg irons on him, and took him to jail. A month later, he was taken by train to McLean Barracks in Cincinnati for a court-martial along with seven other men accused of conspiracy. He was confined in a cold cell, where water dripped continually from the ceiling. Rheumatism began to bother him, but he said he could stand the pain. “I am a soldier,” Grenfel wrote. “I can bear my fate.”

Grenfel’s day in court was delayed while the army prosecutor questioned witnesses. “The president of the court martial described me as the white-haired leader of the conspirators, riding a white charger into Chicago,” Grenfel wrote to the editor of Harper’s Monthly Magazine. “Nothing can be further from the truth….” But the editor refused to publish Grenfel’s effort to set the record straight.

The trial began in January 1865. Some of the witnesses turned state’s evidence, but only one, ex-Confederate John T. Shanks, linked Grenfel with Hines. Robert Hervey, Grenfel’s young, determined lawyer, offered a vigorous defense, questioning the credibility of witness after witness. But in the end, the tribunal gave prison terms to all the convicts except Grenfel, who was sentenced to hang.

Hervey inundated every official in Washington with legal briefs exposing falsehoods in the testimony. He showed clearly that the trial record contained nary a scrap of unimpeachable evidence to link Grenfel with Hines or the conspiracy. He sent Stanton, Lincoln, and others scores of legal briefs that pointed out the prior criminal activity of the government’s witnesses, in an effort to discredit them. It was a sound tactic; the government’s case was based solely on the witnesses’ testimony, with no substantive corroboration or incriminating physical evidence.

Back in England, Grenfel’s family, which apparently had considerable influence in British politics, must have exerted some pressure; Parliament demanded action in the case, and the British ambassador to the United States tried to save Grenfel from the hangman. Finally, President Johnson gave in and commuted Grenfel’s sentence to life imprisonment in Fort Jefferson, a federal prison 50 miles west of Key West in Florida’s Dry Tortugas island chain.

It was a scorching day in June 1866 when the former slave ship Alice Carter ferried Grenfel and 16 other shackled prisoners from the Key West Naval Depot to Fort Jefferson. The fort stood on Garden Key, which at 15 acres was the largest island in the Dry Tortugas group. Garden Key rose just above sea level, barely enough to support the six-sided brick structure that shone yellow in the bright southern Florida sunshine. Prickly pear and sea grass covered the ground around the fort. Within a few miles there were three other islands. One of them, Logger Key, had a lighthouse.

Grenfel lumbered across the drawbridge over Fort Jefferson’s wide moat, his chains clanking with every move. Guards probably pointed out a shark or two in the water as he passed. In the courtyard beyond the drawbridge, listless inmates cleaned and polished the fort’s bricks. Each was bound at one ankle by a chain that led to a 30-pound iron ball. It was apparent that the prison commandant was a no-nonsense type. He refused to recognize Grenfel’s officer rank and had him chained to a ball in short order.

Hardship was nothing new for Grenfel, but he found prison life particularly brutal. Heavy work loading coal and bricks, combined with a spare diet and rheumatism, put a terrible strain on the 66-year-old man. In letters to his daughter, he described in detail some of the barbarities he and other inmates endured. When he was unable to load bricks due to stiff joints, he was beaten and kicked. At least once, he was bound and tossed into the sea repeatedly until he lost consciousness. Abuses were so frequent and violent that Grenfel lost his desire to live. “I am dying by inches…,” he wrote. “The sooner the better….”

His family in England apparently responded by putting more pressure on British officials, this time imploring the government to protest brutalities at the prison. The U.S. State Department did get involved, and so did the Florida legislature, sending a resolution to Stanton pleading for Grenfel’s release. But nothing happened.

Grenfel was bitter. Perhaps Stanton remembered the deceit Grenfel had practiced in his office in 1864. Perhaps he was responsible for the United States’ false reply to the British that Grenfel was in good health and was doing light work. Grenfel, however, saved his criticism for the British government. “The British Lion puts its tail between its legs when Jonathan gets mad,” he said. “Seward rules in Downing Street as much as in Washington…. Adieu, with love, too all those who once loved me….”

The old warrior’s condition continued to deteriorate. His health almost completely broken, he found himself confined to the dungeon. It was then that he began plotting an escape from the prison–about the same time a boatload of new prisoners was delivered to the island. One of those prisoners was Dr. Samuel Mudd, the physician who set the leg that John Wilkes Booth broke during his escape after assassinating President Abraham Lincoln on April 14. Three other people convicted of conspiring in the assassination were also among the new inmates. Mudd’s arrival was a blessing of sorts for Grenfel; the doctor wasted no time in insulting a guard and found himself taking Grenfel’s place in the dungeon. Grenfel got a much-needed return to fresh air and sunlight.

Then a dark cloud descended, silver lining leading the way. A boat delivered a load of much-needed supplies and a new commandant, a Major Stone. After surveying the situation, Stone had the provost of the guard arrested and sent away. He further endeared himself to the prisoners by relaxing the stringent rules and granting some freedoms. But along with the good came the bad, namely yellow fever, a highly contagious disease known more bluntly as the “black vomit.” No one in those days knew how to contain the disease, and it spread rapidly. Within days, the new commandant and his young son were dead. The prison surgeon died, and so did many prisoners.

Dr. Mudd was the man best suited to tend to the ill quarantined in the prison. He accepted the task that fate had handed him and reported to the pesthouse to treat the victims. At his side was Grenfel. For three months the two men worked together, in Grenfel’s words, as “Doctor Mudd, chief physician; Colonel Grenfel, chief nurse.” They labored in deplorable conditions, distributing medicine, washing and feeding desperately ill men, and comforting the dying.

Prison records show the disease struck 300 men and killed 40. Those who died were buried the same day on adjacent Bird Key. Mudd himself finally came down with the fever, but survived thanks to the efforts of Grenfel and two other men convicted in the Lincoln assassination.

Finally the epidemic abated. Completely exhausted by the ordeal, Grenfel left the stinking gunroom where he and Mudd had been stuck for three months. He was given light work to do. In spare time, he planted a large garden and his letters to his daughter mentioned the quality of the vegetables. He boasted of his “radishes, tomatoes and pepper in bloom, and peas and beans at maturity.”

A few months later, he learned that his last, best hope for freedom had been dashed. Federal authorities overlooked his samaritanism and reaffirmed their ruling for him to die in prison. If they had their way, he would meet his demise as a far different man than he had been all his life. “They have turned my sword into a shovel and rake,” he wrote, “and I am at the head of my profession.” But it was not his chosen profession. So rather than die a gardener, Grenfel took his fate into his own hands, as he always had, and died an adventurer.

Walter Haefele of Camino, California, wrote an article about Reuel Gridley, a U.S. Sanitary Commission auctioneer, for the March 1988 issue of Civil War Times.