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  Taking up residence with his wife on St. Peter Street in the French Quarter, Whitley operated throughout 1860 as a kind of itinerant merchant, peddling his wares, mostly sugar and molasses, among the cotton plantations and steamboat landings that lined the Red and Mississippi Rivers, between New Orleans and Shreveport.21 By this time, the entire United States was coming apart over the same conflict between pro-and antislavery forces that had bloodied Kansas during Whitley’s time there. Louisiana, with its vast cotton and sugar plantations worked by thousands of enslaved African Americans, belonged firmly in the pro-slavery camp. Roughly a year after Whitley’s arrival, on January 22, 1861, a convention of white politicians declared that the state would secede from the Union.

  When Hiram C. Whitley betrayed and ambushed abolitionist John Doy and his party of escaping African Americans, he had no idea Doy would not only avoid lynching or prison in Missouri, but would also publish a memoir of his experience

  Whitley stayed in the city, perhaps still fearing that his Kansas past would come back to haunt him if he tried to flee to federally held territory, as many other Northerners living in New Orleans had done, or perhaps unable to afford the trip. He voiced rebel sympathies and from time to time drilled with various military companies being assembled to wage war on behalf of the fledgling Confederacy—but each time his unit was about to be sent into battle, he managed to avoid service by feigning a disability.

  For her part, Catherine felt as if she were under house arrest during rebel rule. Whitley, too, was under stress; so much so, perhaps, that he lost his temper and beat a fellow citizen with a cane, which landed him in Orleans Parish court on a charge of assault and battery “without due provocation.”22

  Fortunately for both of the Whitleys, the United States military reoccupied New Orleans before Catherine could succumb to depression, and while Hiram was still out on bail. The day the Union forces arrived—May 1, 1862—Catherine sat by her window gazing at a flagpole atop the United States mint, anticipating joyfully the national banner’s reappearance.23

  Her husband, however, was in Shreveport—the Confederate-ruled Red River steamboat hub seven hundred miles to the north—ostensibly on business. When Shreveport’s authorities learned that the Union had retaken New Orleans, they immediately hatched a plan to prevent a Union riverine advance on their city: volunteers would drive the one-hundred-sixty-two-foot-long side-wheel steamboat, Starlight, a few dozen miles south along the Red River and scuttle it, turning the submerged vessel into a barrier against Union boats.24

  Whitley signed up for the mission, but not because he wanted to help it succeed. Instead he saw a chance to get back to New Orleans, Catherine, and whatever opportunities might be in the offing under its new Union authorities. On the first night aboard the side-wheeler, as his supposed rebel comrades slept, Whitley stole a lifeboat and quietly paddled it away, aided by two of the Starlight’s African American crew; he promised to protect them in return for help reaching what was now the largest city in the South held by the forces of Abraham Lincoln.

  Traveling on the water at night, sleeping in bushes on the riverbanks by day, Whitley and the two black men made it to New Orleans in less than a week, whereupon Whitley walked to the United States Army’s makeshift headquarters at the St. Charles Hotel and presented himself as a source of intelligence on the rebel-held areas to the north.

  He was in luck: the commanding general, Benjamin Butler, hailed from Massachusetts, Whitley’s sometime home state. These common origins helped Whitley gain an audience, and to overcome the inevitable suspicions that he might be a Confederate double agent. To win the Union military’s full confidence, however, Whitley proposed to put his knowledge of the Red River steamboat trade to work for them. The specific act of sabotage he suggested was audacious: to cross rebel lines at Alexandria, Louisiana, a commercial center on the Red River, two hundred miles northwest of New Orleans, and hijack the New Falls City, a three-hundred-foot steamboat that the Confederates were using to transport men and supplies.

  Far-fetched though it seemed, Butler approved the mission, promising Whitley $20,000 if he succeeded, and warning him the Union would not come to his rescue if he ran into trouble. Retracing the same route he had just traveled to escape rebel territory, Whitley soon reached Alexandria, disguised as a rebel soldier and accompanied by a steamboat engineer from New Orleans whose assignment it would be to drive the boat once Whitley commandeered it. For several days, Whitley talked his way into the confidence of the watchman on the New Falls City, while his engineer companion lay low in a safe house. Finally, one of Whitley’s drinking sessions with the watchman ended with the latter unconscious, as Whitley had planned. He summoned the engineer—who suddenly realized he had no idea how to drive the huge side-wheeler.

  Whitley fumed but did not panic. Continuing to pose as a rebel, and drawing on his prewar experience trading along the Red River, he offered to help move a shipment of supplies to flooded-out rebel villages east of Alexandria. A merchant accepted Whitley’s offer and gratefully arranged the necessary safe-conduct documents. Whitley then used the passes, not to resupply the Confederates, as promised, but to move through rebel-held territory between Alexandria and the Union lines, where he slipped across no-man’s-land and returned to New Orleans.

  When Whitley appeared again at the St. Charles Hotel, Butler laughed heartily at his tale. Disappointed Whitley had not brought him the steamboat, he was nevertheless impressed with the intelligence Whitley gained on his trip, and with the knack for survival and steady nerves he had demonstrated in procuring it.25

  The general promptly assigned Whitley to the staff of the United States Army’s provost marshal, the officer in charge of fighting crime, suppressing rebel sentiment, and ferreting out Confederate spies and saboteurs. During the second half of 1862, Whitley operated as Butler’s all-purpose spy among the civilian population. When rebel sympathizers tried to hide silver and jewels in the city’s cemeteries’ unique aboveground tombs, protecting their wealth from Yankee taxation, Whitley exposed their plot and broke up a fake funeral before the “mourners” had time to “entomb” a coffin filled with necklaces, spoons, and candlesticks. When thousands of New Orleans residents claimed to be French or British citizens, entitled to protection against the Union from those foreign sovereigns, Whitley blew open a safe containing the city voting records proving they were Americans.

  For the first time in his career, Whitley had to contend with counterfeiters. In October 1862 the city saw a surge in fake railroad tickets, suspected to be the handiwork of a gang led by Nicolas Gregorio, a Sicilian immigrant, and Andrew Feeley, a recent escapee from state prison. Whitley arrested one of their street dealers with phony tickets in his possession and offered the suspect his freedom if he would set up a meeting to buy more tickets from Gregorio with Whitley, in disguise, as his companion. As soon as the purchase was completed, Whitley arrested the gangster. In due course, he discovered an entire factory for the counterfeit tickets; Gregorio and Feeley were sentenced to two years each in prison.26

  Not all such cases ended in convictions. When counterfeit two-dollar bills began to circulate, Whitley traced the phony money’s origins all the way to General Benjamin Butler’s own private secretary, an expert forger—whom Butler allowed to go free, sparing himself an embarrassing scandal.

  And in New Orleans, for the first time, Hiram C. Whitley killed a man.27

  * * *

  Louisiana’s state prison at Baton Rouge had been in the cross fire between Union and Confederate troops during 1862; many prisoners, including Andrew Feeley, managed to escape amid the confusion and destruction. After his success against the counterfeiters, the provost marshal assigned Whitley to capture an especially dangerous escapee, Pedro Capdeville, a convicted burglar, who was rumored to have killed fourteen men during his outlaw career.

  By noon on January 6, 1863, Whitley had tracked a man he believed to be Capdeville to a French Qu
arter restaurant. Interrupting the suspect’s lunch, Whitley announced himself as an officer of the law. The two struggled, and Whitley spotted what looked like a knife in his quarry’s hand. He pulled back; the suspect broke free. Whitley fired his revolver at the man’s back as the latter sprinted out the restaurant’s back door. Following as fast as he could in the muddy unpaved street, Whitley cried out “Stop him! Stop him!” and fired again, from half a block away. The suspect fell, badly wounded. Whitley handcuffed him and took him to the city’s Charité Hospital.

  Whitley had escaped a sticky situation, but it was not clear that he had actually shot Pedro Capdeville. As he lay dying at the hospital, the man protested that he was a victim of mistaken identity. His name was Jean Louis Stella, he said, and he was a native of France. Stella was indeed the name he had given when Whitley, dressed in plain clothes, first demanded he identify himself in the restaurant. Just before he expired, the man admitted he had done prison time for larceny, but insisted he knew Capdeville well from his stint behind bars and that the latter had gone away to join the Confederate Army.

  The shooting, in broad daylight on a busy street, caused an uproar; rebel sympathizers in New Orleans depicted it as yet more evidence of Union oppression. To soothe public opinion, the military authorities organized an inquest, at which three witnesses—the restaurant owner and two former policemen—testified that the man Whitley had killed was Jean Louis Stella and Pedro Capdeville. The latter name, they explained, was Stella’s alias. With Whitley’s quarry now dead and unable to contradict those claims, the detective was cleared of any wrongdoing.

  Still, the episode demonstrated the risks to the Army of having agents like Whitley roam the city, serving the military but, as nominal civilians, not formally subject to military discipline. In 1863, another Massachusetts man, General Nathaniel Banks, replaced Butler as the Union commander in New Orleans. Under Banks, the Army decided to enroll Hiram C. Whitley formally in the ranks—as a major. Worried that the rebels might mount an attack on the Crescent City, the Army was recruiting reinforcements at the time, and Whitley’s assignment was to train the new 7th Louisiana Volunteer Infantry, drawn mainly from the city’s large population of free black and mixed-race men, known as the gens de couleur libre, or “free people of color.”28

  A spy, saboteur, and detective with no military experience, Whitley lacked preparation for leading troops. His subordinates, meanwhile, were drawn from a population with a long, proud tradition of self-sufficiency in New Orleans, going back to the city’s founding by the French in 1718. One source of that pride was the military service that the Crescent City’s free black men had rendered in the American victory at the Battle of New Orleans in 1815.

  The only known photograph of Hiram C. Whitley as a United States Army officer during the Union occupation of New Orleans. (Danforth W. Austin Family Collection)

  The pitfalls of this situation became evident soon after Whitley accepted his commission in July 1863, when three of his new soldiers of color balked at his order to dig latrines. Whitley ordered the men arrested, then instructed a nearby artillery unit to aim its guns at them, from a spot where the detainees could view the cannon pointed in their direction. “You see that battery?” Whitley barked. “It’s trained on this camp, and if resistance is offered to my commands, you will all be blown to hell in short order.”29

  He then forced the men’s hands behind their backs, and tied them together by the thumbs, holding the three soldiers in that painful position until they agreed to do his bidding. Two quickly yielded, but a third said he would rather die. He fainted in the brutal summer heat as Whitley stood over him.

  As word of Whitley’s methods spread, dissension rose in the ranks, and Whitley ringed the installation with loyal forces to prevent a mutiny. Finally, lower-ranking white officers came to him with a proposed solution: other soldiers had offered to do the digging he demanded, so there was no need to continue torturing anyone who had balked.

  This troubled regiment lasted three months, until the threat of a rebel attack passed and the Army dissolved the unit in October 1863. For a brief time thereafter, Whitley held a provisional commission as a lieutenant colonel, but never actually served in any organized unit at that rank; he resumed working instead as an undercover agent. He repeatedly went on scouting missions in rebel-held territory and bloodied himself again, in a clash between rebel guerrillas and an Illinois cavalry unit that he was guiding through a contested area near Baton Rouge. The skirmish ended with seven Confederates dead.

  In 1865, Whitley aided an Army investigation into procurement fraud among the forces headquartered in New Orleans. After the war, he auctioned off a stockpile of surplus federal military supplies in Texas—then returned to Cambridge, where he arrived in 1866, accompanied by Catherine and planning to establish himself in business again, in the hope that, at last, sufficient time had elapsed since his contretemps with R. M. Campbell.

  He soon faced accusations that ranged from swindling an apothecary out of his shop to selling fake whiskey and diamonds. Though Whitley avoided criminal liability, local authorities stripped him of his pawnbroker’s license. By 1867, Whitley had moved to Washington, looking for government work.30

  In the nation’s capital, his old connection to Benjamin Butler, and the latter’s esteem for his abilities as an undercover man, served him well. Having been a member of Congress from Massachusetts before taking a leave from politics to fight the Civil War, Butler was now back in the House of Representatives as one of the body’s leading “radical” proponents of Reconstruction. His letter of recommendation secured Whitley a temporary appointment as a special agent for the Treasury Department, in which capacity he worked as an investigator for the House Republicans’ effort, led by Butler, to impeach President Andrew Johnson.

  That assignment led to a job interview for Whitley with yet another former Union general who was serving as commissioner of Internal Revenue. Brandishing Butler’s recommendation, Whitley boldly declared he had knowledge of the illegal, untaxed whiskey-distilling epidemic that was so badly draining government finances and hampering efforts to pay off the Civil War debt. He offered to devote himself to the federal fight against it, without pay.

  It was an audacious gesture, reminiscent of Whitley’s initial meeting with Butler in New Orleans five years earlier, in which he had offered to hijack the New Falls City. Like that gambit, this one worked.

  “I have made up my mind to give you a sixty-day commission, and try you,” the commissioner told Whitley. “I want you to go to Kansas.”

  “Any place will suit me,” Whitley instantly replied.31

  * * *

  Across the vastness of America, Hiram C. Whitley had traveled a mighty distance since his days at the Western Reserve Seminary. He had struggled for economic gain, on land and sea. He had spied on abolitionists before the Civil War and rebels during the conflict. He had run for his life across the Kansas Territory to Pikes Peak, and gunned down a man who was trying to do the same on the backstreets of New Orleans.

  In that time, he had boldly and astutely used deception, or force, or his own undeniable charm, to take advantage of opportunities—and his fellow man. He could be a con artist, and a bully; and those aspects of his character had gotten him into one tight spot after another, then helped get him out.

  Yet a young woman of religious principle, Catherine—a believer in high-minded causes like the abolition of slavery and the integrity of the American Union—saw something redeeming in him. She had placed her faith in Hiram C. Whitley, married him, and apparently felt committed enough to him to leave her family home on the Charles River and follow him, from the Great Plains to the Gulf of Mexico.

  When it was time to make the most consequential political choice of his era, Whitley had thrown in his lot with the government of the United States, which was not only the winning side in the Civil War, but also the side people like his wife fervently regarde
d as the right one.

  Having emerged from the cataclysm of Civil War larger and more powerful than ever before, the government, led by Abraham Lincoln’s Republican Party, faced the enormous challenges of extending its writ, establishing law and order, and ordaining freedom, from the defeated South to the still-unconquered West.

  The Republican authorities in Washington were building a nation, and forming a state, all at the same time. These men believed that the same federal legal authority that had been placed in the service of Southern slaveholders—through the Fugitive Slave Act and other measures—could now be turned to the Party of Lincoln’s political advantage, and employed for the sake of national unity and human equality.

  They did not necessarily know, or care, about every detail of Hiram C. Whitley’s career. What they saw in him was someone who could get results.

  At the same time, Whitley’s amoral attitude toward the great issues of slavery and equality, so evident in his slave-hunting in Kansas and in his treatment of his troops in New Orleans, seemed to be evolving. The cruelty inflicted on enslaved people in Louisiana was so ugly that it could shock even his conscience, and, in one case, spur him to action.

  In the first week of July 1863, just as the Union scored pivotal victories at Vicksburg and Gettysburg, James Walkinshow, a plantation overseer in Union-held Lafourche Parish, south of New Orleans, assaulted and stabbed an enslaved African American known as George. The overseer had accused George of working too slowly, then flew into a rage when the black man denied the white man’s charge. “The Yankees have spoiled you niggers, but I’ll be even with you,” Walkinshow roared, reaching for his dagger. Exhausted and bleeding from the stab wound, George escaped to nearby woods, where Walkinshow found him, tied him up, and whipped him. When he had recovered enough to do so, George fled the plantation again and found his way to United States Army headquarters in New Orleans, where he presented his story to a detective on the provost marshal’s staff.