Former schoolteacher finds a fitting home as one of John Hunt Morgan’s vaunted Cavalry raiders

Thomas Henry Hines’ war began in 1861, when he left his Kentucky home to fight for the South. He rose swiftly from lieutenant in a local Kentucky cavalry unit to captain under Confederate raider John Hunt Morgan, the fabled “Thunderbolt of the Confederacy.” He also became a hunted and highly placed special agent, and a major provocateur for President Jefferson Davis. During his service, Hines staged the most sensational prison break of the war and endeavored—in the end, unsuccessfully—to establish a powerful Confederate Second Front in the heart of the Union itself.

Hines was a slim, handsome young man, bearing an uncanny resemblance to John Wilkes Booth. To fellow Confederate agent John Headley, he was “modest and unassuming…endowed with varied talents and unflinching courage….His exploits…in Morgan’s Cavalry are too numerous to be recorded here.” Hines’ superior officer, Major John B. Castleman, added that, with but one exception, he had never known “a man so resourceful and so composed in all difficulties.” It was these qualities that made Hines an ideal member of Morgan’s guerrilla band.

At the beginning of hostilities, 22-year-old Thomas Hines was earning his living as a schoolteacher. He soon left his position to lead a homegrown volunteer cavalry company calling itself the Buckner Guides, named for Brig. Gen. Simon Bolivar Buckner, a fellow Kentuckian. After the Guides disbanded in May 1862, Hines—having lost his lieutenant’s rank in the now-defunct unit—enlisted as a private in the 9th Kentucky Cavalry, Morgan’s command.

Hines found he was well-suited to Morgan’s Cavalry, which one chronicler described as “the most celebrated and flamboyant detachment in the Confederate Army.” Morgan discovered a kindred spirit in Hines, and he soon commissioned the young man a captain. For months, Hines led guerrilla raids from Tennessee into Kentucky, destroying Union trains and depots, “liberating” livestock, and earning a reputation for boldness and daring. He also acted as secret liaison between Morgan and the state’s Southern sympathizers, keeping clandestine meetings dressed in civilian attire and risking capture and death.

Citizens of Old Washington, Ohio, scatter as Morgan’s Raiders—so-called Freebooters—swarm through town during Morgan’s devastating raid of June-July 1863. (North Swind Picture Archives/Alamy Stock Photo)
Citizens of Old Washington, Ohio, scatter as Morgan’s Raiders—so-called Freebooters—swarm through town during Morgan’s devastating raid of June-July 1863. (North Swind Picture Archives/Alamy Stock Photo)

By that time, the “High Tide of the Confederacy” was ebbing and the lightning raids of men such as Hines and Morgan not only diverted the Union Army’s attention, they boosted Southern morale. When Hines led his men into South Union Depot, Ky., burning the Yankee station and destroying a steamboat full of provisions, the news quickly spread throughout the Confederacy.

In June 1863, Morgan sent Hines and 25 men north into Indiana disguised as Union cavalry. His dual mission was to find the best places for Morgan to cross on a planned raid into the North, and to ascertain the presence and number of Southern sympathizers in the area. These pro-Southern citizens were disparagingly known to their fellow Northerners as “Copperheads,” and Hines was to determine their willingness to support Morgan’s forthcoming raid.

Hines’ patrol was discovered, however, and after a desperate chase, they escaped capture only by swimming the Ohio River. His appetite whetted for clandestine operations, Hines would soon have an opportunity to play a much more significant role behind enemy lines.

Though Morgan’s Raid (June 11–July 26, 1863) advanced farther into the North than any other Confederate unit the entire war, it was ill-advised. Displaying his usual boldness, Morgan led his Raiders across the Ohio River into Indiana and then Ohio. But the raid ended poorly. Morgan took heavy casualties and, ultimately, he and more than a thousand of his men were captured. Most were sent to prisoner-of-war camps, but Morgan and a handful of his officers—including Hines—were incarcerated at the Ohio State Penitentiary.

After four months in prison, the resourceful Hines discovered an air chamber under the floor, and, using only two knives, he and his cellmates proceeded to dig a tunnel. After three weeks’ labor, he, Morgan, and six others crawled under the prison, scaled the 25-foot wall, and escaped. Before entering the 18-inch-wide tunnel, Hines, in a rare act of bravado, left a note addressed to the warden, explaining in succinct, respectful detail how he had managed the breakout.

Hines had already achieved fame in the Rebel army as a guerrilla raider; now he was a legend.

By 1864, the South had had crippling defeats at Gettysburg and Vicksburg, and it was becoming apparent Confederate prospects were on the wane. As Jefferson Davis saw it, drastic action was needed, and he called for a war of attrition that would drag on long enough, and cause the North sufficient anguish, to bring the federal government to the bargaining table. It would entail a three-pronged campaign. One aspect involved what historians have labeled the Confederacy’s “dirty war.” Desperate plots were hatched to set ablaze the North’s major cities, including New York and Chicago, while agents pursued plans to poison New York’s water supply, spread yellow fever and smallpox throughout the North, and assassinate its political leaders. Writes chronicler Jane Singer: “[T]he intent of the plotters was always clear: kill, terrify, and demoralize.”

Hines’ dazzling November 1863 escape from captivity in Ohio. (002 Images/Alamy Stock Photo)
Hines’ dazzling November 1863 escape from captivity in Ohio. (002 Images/Alamy Stock Photo)

The second part entailed uniting the Copperheads in the North to form a “fire in the rear.” A significant number of citizens living in the Northwestern states—mainly Indiana, Ohio, and Illinois—were Southern sympathizers and hostile to the Lincoln administration. Many had formed themselves into secret societies such as the Knights of the Columbian Star, Sons of Liberty, Knights of the Golden Circle, and the Order of American Knights. It was the Davis’ goal to arm and unite them as a military force.

Finally, it was the Confederate president’s objective to liberate the various prisoner-of-war camps throughout the North and release tens of thousands of Confederate soldiers—presumably to join with the Copperheads—on a southward path of destruction. He was inspired by Hines’ daring escape. As Hines later wrote, referring to himself in the third person, “Captain Hines had escaped with General Morgan from the Ohio penitentiary. Mr. Davis’ attention was attracted to him by this circumstance, which perhaps contributed to suggest the idea of a general release of prisoners.” The young captain might have been unduly modest; some accounts, in fact, insist that Hines himself brought the idea to Davis, who found the concept “highly feasible.”

Davis assigned Jacob Thompson and Clement C. Clay as commissioners to direct the overall implementation of the ambitious plan and allotted $600,000 in gold—a tremendous amount of money at the time—to the project. The Confederate president also took the precaution of establishing a base of operations outside the borders of both the Union and the Confederacy. “I hereby direct you,” Davis wrote Thompson on April 27, 1864, “to proceed at once to Canada, there to carry out such instructions as you have received from me…in such manner as shall seem most likely to the furtherance of the interest of the Confederate States of America….” The reasoning was sound: Rebel agents and activists could enter the Union on their various missions, and cross back into the safety of neutral Canada. Ontario, or as it was known at the time, “Canada West,” swiftly became the gathering place for veterans of Morgan’s Raiders, as well as escaped Rebel prisoners, arsonists, chemists, would-be assassins, adventurers—and Thomas Henry Hines.

Jefferson Davis and his secretary of war, James A. Seddon, placed Hines at the helm as director of military operations, with orders to cause the release of the imprisoned soldiers and organize them, as well as the members of the various Copperhead secret organizations, into a viable fighting force. He was directed, in part, to “effect any fair and appropriate enterprises of war against our enemies….” Ordered to Canada, he was responsible only to Commissioner Thompson.

Hines immediately made his way north in disguise through the United States and into Ontario, stopping at various locations to confer secretly with Southern sympathizers. He took to his new position with alacrity. In June, Hines sent a coded missive to Secretary Seddon, laying out a portion of his “Plan for a Revolutionary Movement in the West.” He recommends that a diversionary “force be thrown into the state of KY,” while “[t]he Confederates in Canada, together with two regiments in process of formation in Chicago, will be placed under my command to move on that place [i.e., Chicago] for the release of the five thousand prisoners at Camp Douglas. Simultaneous with this movement, the Democrats in every county of Ill. and portions of Ind. and Ohio will rally to arms. A force of three thousand Democrats…will march upon Rock Island for the release of the seven thousand prisoners. At that point, five thousand will move upon Indianapolis, where there are six thousand prisoners.”

The Raiders’ foray into St. Albans, Vt., in late 1864 proved mostly a nuisance. (Lebrecht Music & Arts/Alamy Stock Photo)
The Raiders’ foray into St. Albans, Vt., in late 1864 proved mostly a nuisance. (Lebrecht Music & Arts/Alamy Stock Photo)

Hines went on to assure Seddon that “the state governments of Ind. Ohio and Ill. will be seized and their executive heads disposed of. By this means, we hope to have, in ten days after the Movement has begun[,] a force of fifty thousand men.” He proposed to hold Camp Douglas with his force of freed prisoners, and if unable to do so, “to retreat through Ind. to KY.” After informing Seddon that the Movement would begin “on or about the twentieth of July,” Hines assured him that “the people were never so ripe for revolution.” Once he had neutralized the governments of these states, replacing their executive officers with Copperheads, he would lead thousands of released prisoners on an attack on Nashville, Tenn.

While these numbers might appear fantastic, Hines and Thompson had been assured that such a force could easily be mustered and brought into Confederate service. Clement Vallandigham, famed antiwar activist and self-appointed prophet of the pro-Southern Sons of Liberty, had assured Hines that some 175,000 members of the secret society in Illinois, Indiana, and Ohio stood ready to rally to the cause.

Hines’ elaborate and ambitious scheme depended almost entirely on the willingness of the Copperheads to put their lives on the line. Ominously, however, the Copperhead leaders found excuses to push back the launch date three times, into late August.

Armed and in disguise, Hines traveled with 60 men to Chicago for the August Democratic convention, confident they would set the spark of rebellion ablaze among the Copperheads. But Hines was a dedicated Southern patriot and combat veteran, whereas the myriad Copperhead malcontents had ventured nothing beyond voicing their discontent. As Bruce Catton wrote, “Thompson and Hines…made the same mistake; when they looked upon the vast body of supposedly militant Northern Copperheads; they took them seriously.”

When the thousands of promised volunteers failed to materialize, Hines begged for 500 men with whom to free the prisoners from just one camp. No one stepped forward. With the reality of turning inflammatory rhetoric into a fight with real bullets, and the possibility of the gallows waiting for those who survived, the promised Copperhead army did not materialize and Hines returned to Canada.

Assured anew by Copperhead leaders that they would rise on Election Day in November, the ever-
optimistic Hines once again traveled to Chicago. This time, he was determined to free only the prisoners at Camp Douglas and required only sufficient Copperhead assistance to overcome the camp’s garrison. However, two informers gave up the plot, and more than 100 men were seized, along with a large store of guns and ammunition.

Hines escaped with difficulty and made his way to Richmond, where he reported to Seddon on the “attempt, betrayal and failure” of his mission. He naively suggested that the plot was still feasible but acknowledged that the Copperhead societies in general were not to be relied upon. By now, however, it was too late for further action. Hines was ordered back to Canada, where he used the government’s money to help alleviate the legal difficulties of those fellow conspirators who had been captured.

The abortive Chicago rising was not the only aspect of the Northwest Conspiracy to fail. An attempt to liberate Johnson’s Island, the prisoner-of-war camp on Lake Erie, came to naught, as did the elaborate plan to set New York City aflame. The two major players in these actions were ultimately captured and hanged. A plan to blow up the White House was discovered and neutralized, as was the scheme to create a yellow fever pandemic through the distribution of infected blankets. Only the plot to rob and burn St. Albans, Vt., a small town near the Canadian border, was moderately successful. A uniformed band of former Morgan’s Raiders did, in fact, make off with the local bank’s cash, escaping into Canada, but they failed to burn the town.

Ultimately, the Northwest Conspiracy foundered due to a lack of support from the Copperheads, the activities of informers, double agents, and federal spies, and the fatal flaws that inevitably afflict grandiose schemes. With the South’s surrender, some of its most dedicated servants were left stranded in Canada.

Given the vengeful mood now permeating the Republican-led federal government, Hines deemed it wise to remain in Canada. He was far from alone; sharing his exile were countless former Confederate agents, generals, and government officials.

Hines’ hope, however, was to return home, for both sentimental and practical reasons. Six months after the surrender at Appomattox, he wrote to an influential Kentuckian: “I am very anxious to return immediately to KY.; and besides, if I decided to remain in Canada, my financial condition would not permit it.” In March 1866, having taken the Oath of Loyalty, he crossed the border into the United States for the last time. “We are determined to live among our own people,” he wrote, “and take their fate whatever that may be. Wellcome [sic] any fate if it be shared among my own people.”

Ever the “unreconstructed” Rebel, Hines refused to follow the path of other former Confederate officers who chose to pursue military careers in blue uniforms. At the end of his exile, he had written in his diary, “By diligence and labor, I will be able to rise.” And rise he did. He entered law school, became editor of a city newspaper, and went on to sit as a judge and, ultimately, the chief justice of the Kentucky Court of Appeals. He had married his sweetheart during the war, and eventually fathered six children. Long life, though, was not in the cards. A month after his wife died in 1898, Hines—not yet 60 and in increasingly poor health—followed.

In retrospect, Thomas Henry Hines was the author of impressive successes and colossal failures. While he cannot be held singly accountable for the ultimate disintegration of the South’s wide-ranging clandestine war, he did, in fact, play a major part, due to both his naivete and his unrealistic expectations. As historian Edward M. Coffman states, “In the last year of the Confederacy, Southern leaders were willing to gamble on illusions which they had long cherished. As their agent, Captain Hines failed…as a master spy. Although few could match his experience in small cavalry operations, Hines’ ability as a subversive agent was open to question.” Ultimately, it was as a dashing officer and guerrilla fighter in Morgan’s Cavalry that Hines achieved his greatest and most dramatic success.

Ron Soodalter writes from Cold Spring, N.Y.