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The Vice President Flees

May 2024
23min read

Branded a traitor by the government he once served, John C. Breckinridge ran a perilous race for freedom rather than risk capture by the North

The weather in the Straits of Florida was turbulent in June of 1865. Throughout that spring the Caribbean boiled from one storm after another, but this latest one was particularly severe. Ocean-going steamers delayed their departures because of it, yet, in its very center, six desperate men bailed and prayed in a sailboat barely seventeen feet long. One of them in particular, a tall, handsome man, might have looked back, if his fevered labors had allowed time for reflection, to a June five years before when, as both senator-elect from Kentucky and Vice President of the United States, he had accepted the nomination of the Democratic party for the Presidency. Now, despised and indicted as a traitor, he was trying to escape the country, certain of imprisonment if captured and fearful of execution.

Before the Civil War, John Cabell Breckinridge’s friends were sure that his was a charmed life. Born in 1821 to a family already prominent in Bluegrass politics, he early assumed a leadership that came naturally to him. After serving in the state legislature, Breckinridge won a seat in Congress in 1851 and held it for two terms, meanwhile revitalizing the ailing Democratic party in his state and winning for himself a meteoric rise in national politics. It came as no great surprise when in the spring of 1856 the Democratic National Convention nominated him to be James Buchanan’s running mate in the coining Presidential contest. Breckinridge, just turned thirty-five, had been constitutionally eligible for the office for only five months. That November he was elected—the youngest Vice President in United States history.

Buchanan’s was a singularly undistinguished administration, and by 1860 his party was fragmented beyond repair. In the growing sectional crisis, most influential Southern politicians favored nominating Breckinridge for the Presidency. Many who actually desired disunion hoped that, if nominated, he would be defeated by the Republican candidate, Abraham Lincoln. This, they felt, would provide an excuse for secession and the setting up of a separate Southern nation. In June, 1860. the Democratic party split, and the Southern faction gave Breckinridge its nomination, pitting him in a four-way battle with Lincoln, the Northern Democrat Stephen A. Douglas, and John Bell, a tired old Whig. Breckinridge, who was so opposed to slavery that he once declared in private that it should be abolished by force if necessary, was no friend of secession, and had not wanted the nomination. But he felt obliged to accept it, and with it took defeat in November. In a matter of days South Carolina withdrew from the Union and war became inevitable.

Late in 1859, when United States Senator John J. Crittenden announced that he would retire from the Senate at the expiration of his term in 1861, the Kentucky legislature set about selecting his successor. Senators were elected then, not by the public, but by their state legislators, and the Bluegrass lawmakers had chosen Breckinridge to take over the Senate seat. Consequently the former Vice President sat in the special session of Congress called by President Lincoln in July, 1861.

Breckinridge took his seat hill of misgivings. He disagreed completely with Lincoln’s war measures, felt that they were responsible for bringing on the first great battle at Bull Run in July, and accused the Republicans of subverting his beloved Constitution. His attacks on the administration became increasingly frequent and bitter. Though he had committed no disloyal acts, the authorities believed him to be dangerous. Finally, while he worked at organizing a series of “peace” picnics in Kentucky that September, the Union military command in his district gave orders for his arrest. Outraged that a citizen and a United States Senator could not freely voice his opposition without fear of arbitrary arrest, Breckinridge made his escape from his home in Lexington and took the step that many had expected him to make for months. He rode to the Confederate capital in Richmond, Virginia, and offered his services to President Jefferson Davis.

Confederates had hoped Breckinridge would join their cause, because they believed his influence could sway the important border state of Kentucky to join them. Davis considered appointing him Secretary of War in his Cabinet but then decided that Breckinridge would be more useful as a brigadier general with the Confederate army quartered at Bowling Green, Kentucky. The new general failed to lure the Bluegrass away from the Union, but his performance in the Battle of Shiloh in early April, 1862, won for him a promotion to major general, and thereafter his star rose as rapidly in war as it had in politics. Breckinridge fought at Corinth, Vicksburg, Baton Rouge, Stone’s River, Chickamauga, Lookout Mountain, Missionary Ridge, Cold Harbor, and Winchester, commanded his own military department in southwest Virginia, and on May 15, 1864, won what has been termed the most important secondary battle of the war at New Market, Virginia.

By February, 1865, Breckinridge had seen wider service in more areas of the Confederacy than any other general officer in the army. His popularity was at its height, and now Davis gave him the appointment as Secretary of War, hoping that this might quell some of the outcry against Davis’ unsuccessful, and now unpopular, administration.

Breckinridge took his Cabinet portfolio convinced that the Confederacy was dying. During his brief service he directed his every action toward seeing that its demise was an honorable one. When Petersburg and Richmond fell to Grant in April, he organized the escape of Davis and the Cabinet to Danville, Virginia, while he himself rode out of the capital to join Robert E. Lee’s army in its retreat toward Appomattox. After consulting with Lee, the Secretary set out to join the fleeing government and reached Danville on April 11, only to find that Davis had gone on to Greensboro, North Carolina. Upon finally joining the president, Breckinridge repeatedly advised capitulation, later taking part in the surrender negotiations between General Joseph E. Johnston, commander of the only remaining Confederate army in the East, and General William T. Sherman. After the discussions were concluded, Sherman took Breckinridge aside and quietly advised him that the people of the North were particularly bitter toward him.

The North was bitter indeed. Some officials were incensed that a man who had been Vice President and a Presidential candidate should have gone over to the Rebels. The Senate had declared him a traitor in December, 1861, and several Federal courts now held indictments against him for high treason. In 1863, when his death in battle was erroneously reported, the New York Times rejoiced, declaring, “Of all the accursed traitors of the land there has been none more heinously false than he—none whose memory will live in darker ignominy.” Breckinridge, Sherman urged, would be well advised to escape the country.

At the same time that he planned for his own flight, the Secretary was also making plans to get Davis out of the country, and the best route seemed to be through Florida. On April 26 they set out, the president and his Cabinet accompanied by a cavalry escort of two to three thousand men, with Breckinridge in command. They rode across the Catawba and into South Carolina, through Unionville, and on to Abbeville, arriving on May 2. There Davis called his last Cabinet meeting, still with the faint hope of continuing the war. It was a wasted effort. His ministers had lost their heart and were resigning almost daily. General Basil Duke, leading part of the escort, felt that of the government leaders only Breckinridge “knew what was going on, what was going to be done, or what ought to he done.”


That night intelligence came that the enemy’s patrols were in the vicinity, already on their trail, and at eleven o’clock they rode off again into the night. The next morning Breckinridge was faced with a near-mutiny when men of the escort refused to go farther without receiving some of their back pay. It took until late in the evening to distribute among them some of the Confederate funds. It was precious time lost. Davis, unable to wait, had gone on ahead with a small party, and now Breckinridge hastened to rejoin him. He arrived in Washington, Georgia, on the morning of May 4, barely an hour after Davis had left.

Here Breckinridge transacted his last business. He put the remaining Confederate monies, about twentyfive thousand dollars, into responsible hands, drew a thousand dollars to help in his escape, and then disbanded the War Department. He also accepted the last official resignation of a Confederate officer, that of Lieutenant James B. Clay, Jr., grandson of Henry Clay, the compromiser who had fought so long and hard to prevent the tragedy that was now in its last act. The next morning Breckinridge dismissed most of the escort, unpacked his valise, and divided his shirts and tobacco among the couriers who had so faithfully followed him this far. Then he set off with about forty-five volunteers as a decoy to lure Federal troops away from the path of the fleeing Davis.

By the next day Breckinridge had gone only eleven miles, waiting for the enemy to find him in hopes that he could delay their pursuit of the president. He had just taken up quarters in a farmhouse when word came that 250 Union cavalrymen were approaching. The Secretary mounted his escort to face the enemy but gave orders that a fight should be avoided. He wished only to win time. There was a parley, with the Federals demanding surrender, and while the talking went on Breckinridge quietly slipped away into the woods, accompanied by his sons Cabell, twenty, and Clifton, eighteen; young Lieutenant Clay; his adjutant, Lieutenant Colonel James Wilson; a black slave named Tom Ferguson, who belonged to a former staff officer; and a handful of friends. He shortly sent back instructions that his escort surrender and go home. “I will not have one of these young men to encounter one hazard more for my sake,” he said, and then rode off to the south.

Breckinridge hoped to rejoin Davis to aid the president’s attempt at escape. First, however, he had to take precautions against being recognized. His years in national politics had made his face well known even in the remote backwoods of Georgia. To combat this the Secretary cut short the long flowing mustache which had become his trademark during the war, put on a black broadcloth suit and his “battle coat”—an old hunting shirt—in place of his uniform, and assumed an alias, “Colonel Cabell.” He rode eleven miles this first day and forty miles on the next, and decided that henceforth he would head for Madison, Florida, a refuge for a number of Confederate fugitives. Before setting out again, however, he sent Clifton and young Clay back to Kentucky. From here on the journey would be too rugged, its outcome too uncertain.

Heavy rains slowed his progress on Monday, May 8, and it was late when his little party finally reached Dublin, Georgia, on the Oconee River. They badly needed food for the ride ahead, and Breckinridge decided to take a chance and send a scout into town for provisions. The Confederates made the necessary purchases without mishap, but at midnight, as Breckinridge and his party were encamped, a patrol of Federal cavalry swooped out of the night and narrowly missed them, riding by so close that the Secretary could make out every detail of their uniforms in the moonlight.

Spurred by this close call, Breckinridge pushed on nearly sixty miles the next day, all of it through rains that turned the country roads into sticky mires. At least the water washed away all sign of his passing. Thus, it was well after midnight when the party, chilled and exhausted, reined up a few miles north of the Ocmulgee River crossing at Jacksonville, Georgia. The Secretary made camp in a dense thicket. When morning came, they were all in a sorry state, the horses utterly broken down. Their only comfort lay in their belief that they were momentarily safe from Federal patrols. They could not know that at that very moment, just forty miles west of them at Irwinville, President Jefferson Davis and his escort were being captured by Union cavalry.

The fugitives needed rest, and Breckinridge stopped for most of the day at a nearby farmhouse, where he was hospitably received, in part because he looked strangely familiar to his hosts. Word got out that important people were here, and soon neighbors “happened” by to visit. They kept staring at him and then at a portrait of Davis on the wall, but no one revealed his true identity. After passing the night the Secretary set out the next morning to cross the Ocmulgee.

They failed to find the expected boat awaiting them at the crossing, and Breckinridge’s guide set out in search of it. The day was pleasant for a change, and the party unsaddled their horses, Ferguson spreading a blanket for the Secretary under the shade of a tree. Then, with the Confederacy—and with it his own career and all hopes for his future—collapsing all around him, Breckinridge lay down to read. The book was, of all things, Plutarch’s Decline and Fall of Athens .


Finally the boat was found, and slowly the Confederates ferried themselves across until only Breckinridge remained on the north bank. Bringing the boat back to get him, Wilson found the Secretary standing on the bank, lost in thought, his eyes looking to the west. He seemed not to hear Wilson’s calls, and when finally he did, he motioned him to wait. Then he spoke softly the words of a popular poem, “Oh! Come to the South,” its last stanza tragically appropriate as he prepared to fly ever farther from his native and beloved land:

Oh! here would thy beauty most brilliantly beam, And life pass away like some delicate dream; Each wish of thy heart should realized be, And this beautiful land seem an Eden to thee.

Those in the boat found themselves “spell-bound by the grandeur of the occasion”; one later noted that “not a word was spoken until after we had crossed, when Breckinridge, springing to his saddled horse, called for us to ‘mount and away.’”


Now the Secretary was deep into Georgia, and on May 11 he stopped at Milltown, just short of the Florida border. He intended to wait here for President Davis, but when word came three days later of the president’s capture, there was nothing to keep him longer, especially with news of a Federal patrol just a few miles north of him. The next day he crossed into Florida, to Madison.

With the aid of General Joseph Finegan, Confederate commander in Florida for over three years, Breckinridge planned his flight through the state. While at Finegan’s home he was joined by Captain John Taylor Wood, grandson of President Zachary Taylor and commander of the Tallahassee , a fugitive Confederate privateer whose captures were second only to the Alabama ’s. Wood had been taken with Davis but managed to get away, and now he would be a great asset to Breckinridge. Together they decided to pass down the Atlantic coast and try to reach the Bahamas.

Breckinridge left his son Cabell and all others but Wood, Wilson, and Ferguson in Madison, for the danger seemed to be increasing. Crossing the Suwannee River, he rode southeast into Gaines ville on May 18, with one Federal patrol moving ahead of him on the same road and another one behind him. A lifeboat captured from the Federal gunboat Columbine was placed at his disposal for the trip down the St. Johns River, and lodgings were arranged ahead for his party as they journeyed to meet it.

The Secretary and his party finally reached the St. Johns on May 26, and their boat was waiting for them. “It was a small, open craft, about 17 or 18 feet long …” wrote Breckinridge. “I thought it might do for the river, but it seemed a very frail thing to go on the ocean in.”

Before embarking down the river, the Kentuckian performed his last official act as Secretary of War, indeed the last official act of the Confederate government. He helped play a joke. Seeking to reward a lieutenant who had acted as guide during the past week, he told him: “You shall be a major; I will make out your commission now.” But the lieutenant seemed unimpressed.

“Well, my friend,”said Breckinridge.

“Well, you see, gineral, thar’s a feller in our regiment what hain’t done nothin', and he is a major and a quartermaster; and if its all the same to you, I would just like to rank him for onst.”

Without delay the Secretary of War wrote out a commission for a lieutenant colonelcy.

With this last act out of the way, Breckinridge’s party boarded the lifeboat and pushed out into the stream. Friends had sent along three recently paroled Confederates, Sergeant Joseph O’Toole, Corporal Richard Russell, and Private P. Murphy, to assist in the escape attempt, so now the fugitive band numbered seven.

It was four o’clock in the afternoon when they began rowing down the St. Johns, and Breckinridge soon discovered that leaving his pursuers behind did not end his troubles. A heavy storm came up in the evening. He anchored the craft in midstream to ride it out but found that there was no room in the boat for anyone to lie down. They passed the night sleeping as they sat, drenched by the downpour, only to discover by morning’s light that the rain had ruined most of the two weeks’ supplies they had purchased. Just as unfortunate was the loss of much of their gunpowder. Breakfast that morning was gloomy: cornmeal mush, with rum and water.

New discomforts presented themselves daily. The mosquitoes were so thick on the banks that the Confederates were forced to anchor in midstream, while in the water itself there were other, more menacing foes. Breckinridge saw “great numbers of crocodiles [actually alligators] who sunned themselves on the bank, and slid into the river with a sullen plunge on our approach. Sometimes they would swim just across our bow with their black scaly backs just visible, like a gun boat low in the water.” The Secretary shot one with his pistol, and it took three more bullets “through the place where his brains should have been” to kill it. And here it was indeed fortunate for the fugitives that Colonel Wilson was along. He seemed inevitably to possess more enthusiasm than good sense, a failing that kept the company in good spirits even in the worst situations. Now, having found a bag of aromatic musk under the alligator’s throat, the enterprising colonel declared that he would put it in a smelling bottle to present to a lady friend whom he proposed to marry. He soon lost the intended gift, but it may not have mattered. He also discovered that he could not remember his beloved’s name.

Private Murphy left the party on the morning of May 29, while the rest rowed on down to Cooke’s Ferry. Here, by prearrangement, a man was ready to haul their boat overland to the Indian River, on which they would continue their flight. Breckinridge spent the night at the Cooke home, and here he was introduced to two of his host’s daughters. They were old friends of Sergeant O’Toole’s, and it did not escape the Secretary’s attention that the swelling middle of one of them indicated a more than casual relationship.


The portage to the Indian was torturous, thanks largely to the indolent wagon driver, his lazy oxen, and the broken-down wagon. “It would have been less labor,” declared Captain Wood, “to have tied the beasts, put them into the boat, and hauled it across” themselves. And now the mosquitoes became so bad at night that they were forced to sit up around a fire in the protection of its smoke. There was no rest.

When Breckinridge reached Carlisle’s Landing on May 31, he discovered that the Indian was no river at all, but a three-hundred-mile arm of the Atlantic separated from the ocean by a slender spit of land, in places no more than a quarter mile wide. Its water was salt, and from now on the fugitives would have to dig in the sand on shore to find the putrid “fresh” water that they needed to survive.

Their first day on the Indian they covered fifty miles, only to battle literally for their lives that night against the mosquitoes. “I cannot give you any adequate idea of these insects,” Breckinridge would write a few weeks later. “They attacked us, not two or three at a time, but in swarms incessantly the whole night long. Both hands were kept going and still they bit us. With his arms tied and his face exposed, I am sure they would kill a man in two nights.” Their only relief was in wrapping themselves in the boat’s sail or in going ashore and burying themselves in the sand.

The rains began again, but the Confederates could rejoice in a minor victory when, on the night of June 2, they approached a Federal guard post at Indian River Inlet. They muffled their oars and stayed in the middle of the river, gliding slowly in the darkness. To their left, on the shore barely one hundred yards away, glimmered the campfire of the guards. It was with intense relief that they passed it unchallenged, unseen, and slid on into the night.

The next morning they went ashore some ten miles below the inlet to find breakfast. All of their provisions were gone now, and they dug in the sand both for water and for turtle eggs, finishing their meal with sour wild limes. Then the fugitives set off again down the river. Spirits rose briefly at the hope of fresh meat when they passed a deer watching them from the bank. For some reason they entrusted the all-important shot to Wilson. “From the manner in which it bounded off, stopping occassionally to look back at us,” Breckinridge reported, “the Col thinks it possible he may have missed the animal.”

Wood and the Secretary had hoped to pass over to the Atlantic side of the sand spit at Jupiter Inlet, but somehow they discovered that it, too, was under Federal guard. As a result, they stopped twenty miles above it at a place where the strip of beach was only a few yards wide, and here they got out and hauled the boat across and into the ocean. Breckinridge and the others suffered quite a start when a steamer passed within a mile of them, but fortunately they went unnoticed. After another day of sailing they tried to head out for the Bahamas on the evening of June 4, but unfavorable winds blew them back on the Florida coast, so that by the next morning they still had not gotten out of sight of land. And then near-disaster struck.


By now the Confederates were somewhat accustomed to dodging the occasional steamers that passed down the coast. This morning, when they saw one coming, it was a matter of routine for them to put in to shore, turn over the boat to make it look like flotsam, and then hide in the chaparral. But when this ship had passed, they returned to the boat too soon. They were seen, and the enemy steamer turned around and made straight for them.

“I thought we were gone,” Breckinridge wrote. He suggested that they all take to the brush in the hope that the Federal ship would leave their boat unmolested, but Wood knew better. The craft would be taken off or destroyed, a move that would be fatal to the fleeing Confederates.

As the steamer lowered a boat full of men armed with cutlasses and pistols, Wood had the Secretary go into the brush, revolvers in his hands, while he, Russell, and O’Toole sailed out to meet the Union sailors. They tried to look as stupid as possible, and said they had come back from getting fresh water inland and were scavenging along the coast looking for wrecks. After some time the Federals finally accepted Wood’s story and rowed off, “much to our relief.”

All that night the head winds continued to blow them back against the coast, and by morning, June 6, they were still sailing along the shore. Soon they hailed a small band of Seminoles camped on the bank, smoked a pipe with them, and were given some “kuntee,” a sort of mush that Breckinridge found “when cooked was a little thicker than a pancake and ten times as tough.” Still, it was the first nourishment they had enjoyed in several days, besides their now constant diet of turtle eggs. Thus fortified, they shoved off again and unwittingly sailed back two hundred years to the age of romance.

That afternoon Breckinridge saw a sail approaching. Immediately their fears told them it was a Federal patrol boat. But then the boat changed course as though to avoid them. Seeing this, Wood suspected that perhaps its occupants were also fugitives, probably Union deserters. And seeing that their boat was much more seaworthy than his, Wood decided to give chase. The Confederates brought in their sail in the light breeze and leaned on the oars. Slowly they overhauled the fleeing boat, and Wood’s pistol shot across her bow ended the chase.

Her three occupants, Federal deserters, seemed terrified at first. After a month of hardship Breckinridge and his companions, unshaven and browned by the sun, looked every bit like buccaneers. The Secretary, in an old blue flannel shirt, wore a gigantic straw hat with a brim so huge that it “flapped over his head like the ears of an elephant,” noted one observer.

The deserters were silent, sullen, when Wood and Breckinridge told them they were prisoners and their boat a prize of war. The renegades were well armed and, though outnumbered, Wood saw that “they were desperate and not disposed to surrender their boat without a tussle.” The Confederates wasted no time. The captain and the Secretary stepped into their boat. When one of the deserters hesitated to step forward as ordered, Breckinridge drew his pistol and pointed it in his face. Wood did the same, and they held him at gunpoint while Wilson disarmed all three. Thoroughly subdued, the deserters made no further resistance.

Wood, the old seaman, could appreciate the situation better than the other Confederates and now acted the part of a buccaneer. He set his vivid imagination to concocting aloud all manner of tortures to inflict upon the captives but finally gave in at letting them off with an exchange of boats. Breckinridge joined in the macabre speculation, and the deserters must have been vastly relieved when the two groups switched boats and they were on their way with their lives. They must have been surprised, too, when at the last minute the Secretary gave them a twenty-dollar gold piece for their boat. As for the Confederates, they rejoiced at their good fortune and decided now to make for Cuba in their new, and much better, craft. Breckinridge himself may have mulled with amusement over his new accomplishment—becoming the first Vice President in history to turn pirate. Only the irrepressible Colonel Wilson was disappointed. He expressed considerable sorrow that they had not made their captives “walk the plank.”


If the Secretary thought his adventures had ended with piracy, though, the next morning proved him dreadfully wrong. Needing supplies for their voyage to Cuba, they moved on down the coast toward a small trading post said to be at Fort Dallas (now Miami). It was daylight when they approached the wharf, only to see twenty or thirty renegades—deserters from both armies and navies, outlaws, and Caribbean cutthroats—awaiting them. “A more motley and villainouslooking crew never trod the deck of one of Captain Kidd’s ships,” Wood later recalled. One ruffian hailed the Confederates and was told that they were wreckers who had left their ship a few miles to the north. Wood hoped to intimidate them with the thought that he had more men back at this fictitious vessel.

The renegades ordered the Confederates to land, but Wood and Breckinridge remained suspicious. A canoe put out from the wharf, but the fugitives refused to be persuaded to trust their boat close in to shore. Finally they told the cutthroats that they would buy their supplies elsewhere and started off down the river. Minutes later they saw five canoes loaded with twenty or more of the desperadoes bearing down on them.

Outnumbered three to one, the Confederates decided to make a stand, and Breckinridge prepared to direct their fire. As soon as the lead canoe came into range, Russell fired a shot that broke two paddles and hit one man. That canoe dropped back, but then the men in the others opened fire, shooting wild. Breckinridge and Ferguson tried shots but missed, and then the Secretary ordered that they conserve their powder for sure shots. Soon Russell and Wilson fired together and hit the lead man in the nearest canoe, nearly tipping it over. Their pursuers now paddled their canoes together and spoke briefly, soon sending one boat forward with a white flag. The Confederates could come and buy whatever they wanted.

After some discussion it was decided that O’Toole would go ashore with one hundred dollars. If he didn’t return safely with provisions within two hours, Wood and Breckinridge threatened to leave and come back with the first Union gunboat they could find, their emptiest threat yet. Time was short now, for they could see a column of black smoke rising near Fort Dallas. The Confederates felt certain it was a signal to bring in more of the cutthroats to overwhelm them.

Breckinridge and Wood waited their two hours, and a half hour more, but still O’Toole did not return. They were forced to conclude that he had been robbed and murdered. Sadly they began to row off down the river. Then a canoe appeared astern. It was the sergeant, bringing with him bread, pork, fresh fruit, water, and a small keg of rum. The famished but relieved Confederates ate their first real meal in weeks while O’Toole recounted his experiences and confirmed their suspicions that the renegades had signalled to friends, who fortunately did not arrive in time.

An already eventful day proved more so when, just after passing Cape Florida, they were chased again, this time by a Federal patrol launch. The pursuit lasted for a grueling four hours, and the fugitives only escaped by discarding almost everything in the boat except their food and rum. With lightened load, they slipped over shallow reefs that the heavier launch could not cross. Late afternoon found them on Key Elliot, hungry, exhausted, and tortured by mosquitoes more than ever before.

With an ocean voyage ahead of them, the Confederates gathered more turtle eggs, coconuts, mollusks, and some waterfowl that, when Breckinridge tried them, proved painfully inedible. Then they were off again, but now the twisting waterways played games with them. With only Breckinridge’s small pocket compass as a guide they wandered back and forth, lost, for hours. It was well after nightfall, near midnight, when finally they passed the Carysfort light and, putting up their sail, ventured out into the dark, lonely sea.

They had a good wind behind them and hoped to pass through the numerous reefs without difficulty. Three miles out, however, Colonel Wilson managed to steer them up on a reef that nearly stove in the boat’s hull. After passing it safely, they moved on into a rising rain squall. Soon the seas ran high around them, and everyone on board except Breckinridge and Wood got seasick. It could not have happened at a worse moment. Weakened, exhausted, starving, the fugitives needed every bit of strength now to fight the elements. Lightning flashing across the skies illuminated terrifying landscapes of wave upon crashing wave all around them. The tortured creaking of their little vessel made Wood fear that each succeeding strain might be the last.


Utterly worn out, Russell and O’Toole were lying sick in the bottom of the boat. Wood was forward trying to take soundings, Ferguson was asleep, Breckinridge was just nodding his head in a doze, and “the celebrated Col Wilson was steering,” when, Breckinridge went on: Suddenly I was roused by a wave going over me and half filling the boat, which leaned over until! the gun wale was under the water. At the same moment I observed that Capt Wood was overboard, and looking round I saw Col Wilson as stiff as a stanchion holding on like grim death to the rudder and the sail rope. It was his grip on the latter that was about to sink us. I knew just enough to shout to him to let go the rope which he did, and the strain being taken off, the boat finally righted. Capt Wood fortunately caught a rope as he went and had scrambled on board. Col Wilson expressed his gratification at the general result and explained that he had thought it his duty to hold every thing lest “it might get some advantage of him.”

Wood, thankful to be alive, took more soundings but found that they were helplessly lost in a maze of reefs and anchored for the night. By morning the seas had calmed somewhat, and they set their course out into the Gulf Stream. A fresh wind carried them swiftly into the Caribbean, but it was not long before the breeze turned into a gale, whipping up the water once again and carrying the little boat completely out of control. From then until the next morning there was no letup. “It seemed to me that she must go under,” wrote Breckinridge. Wood, looking worried and grave as he held the rudder, did not speak. “A worse sea I have never seen,” he wrote in his diary, “a longer one, but not so steep, so quick; how our little boat lived thru it, I hardly know.” At one time the craft lay in a trough between two waves at least twenty feet high, so high that the shadow of one blackened the sail. If chance had turned the boat broadside to them, thought Wood, “our open boat would have filled in a moment & gone down like an egg.” Chances were much against them that night, he later confided to Breckinridge. In nineteen years at sea he had not experienced a worse storm or felt so much in peril.

Morning found them across the worst of the Gulf Stream, but dawn brought new danger when they abruptly came upon a Northern merchant ship, the Neptune . Now desperate for food and water to replace that lost in the storm, Breckinridge and Wood decided to bluff. They sailed right up to the merchantman and boldly demanded food and water. The Yankee skipper looked at them suspiciously, but finally lowered a basket of biscuits and a small keg of fresh water. For the rest of his life Breckinridge believed firmly that after all their trials and the rigors of the storm it was only this handout from an enemy that kept them from perishing at sea.

Exhausted, the men took turns lying down, for there was room in the boat for only one to recline at a time. That evening they sighted the Doubleheaded Shot Keys, small islets off the Cuban shore. Their spirits soaring, the Confederates hoped to make the coast before morning. Soon a lighthouse was spotted, but Colonel Wilson would not let them off without a final neardisaster. Approaching the coast after dark, Wilson steered while Breckinridge and Wood slept. “That enterprising officer,” wrote Breckinridge, “ran the boat nearly on the light house and then concluded to wake us up for consultation.” Before they could do anything, the boat struck a reef with considerable force, and had the sea not been calm, they would have capsized, ending their great journey in tragedy on the very brink of success.

With some effort the boat was righted, and the Confederates sailed on uneventfully to the west until morning. With the dawn they saw the head of a bay and, as they made for it, the white houses and docks of Cardenas. After some difficulty explaining who they were to the port officials, they were finally allowed to come ashore. Cardenas was already well populated with refugee Confederates, and the Cubans themselves, despite their mother country Spain’s official stance of neutrality in the war, seldom hid their sympathy for the Southern cause. As a result, when word of the fugitives’ arrival spread, the town turned out to give Breckinridge a hero’s welcome. It was June 11, 1865, thirty-five days since he had left his escort near Washington, Georgia. Only one other Cabinet member, Secretary of State Judah P. Benjamin, did as well. All the others were captured.


And now, safe at last, the band of adventurers went their separate ways. Their little boat, dubbed the No Name , was sold. Captain Wood soon sailed to Nova Scotia, where he lived out his days. Russell and O’Toole returned to Florida, and Tom Ferguson, now a free man, went back to Alabama to join his family, carrying with him a letter of safe passage and commendation from Breckinridge. Colonel Wilson eventually returned to Kentucky and opened a hotel, writing his old commander, “If my plan of feeding guests on the scantiest cheap fare and charging them the most enormous bill succeeds, I am bound to do well until I am one day killed by some infuriated victim.”

For John C. Breckinridge, however, even arrival in Cuba did not end his trials. Still under indictment in the United States, he lived as an exile in Canada and Europe for the next three and a half years. Not until the general amnesty of Christmas, 1868, did he feel free to return to his beloved Kentucky. When he did, he took up again his law practice. Eschewing politics completely, he nevertheless remained a potent force in the postwar South. At every opportunity he spoke in favor of peaceful reconciliation between North and South, damning the Ku Klux Klan and all other manifestations of extremism. Finally, on May 17, 1875, aged only fifty-four, he died, spent by the labors of an extraordinary life, his death hastened by the hardships of his perilous escape. He breathed his last just ten years from the day when he rode across the Suwannee toward Gainesville to find a boat for his flight to freedom.

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