Emma’s carriage pulled up to Secret Service headquarters, a two-story, lead-colored building at 217 Pennsylvania Avenue, widely said to be “the nation’s most feared address.” A guard ushered her into a room where three Union generals, including George McClellan, waited to interview Frank Thompson. Emma, accustomed to seeing her military hero from afar, galloping through camp on his horse, Dan Webster, was both thrilled and terrified to stand so close to him, as in awe of the general as he clearly was of himself. McClellan was shorter than she’d expected and wonderfully square, thick-throated and broad-chested, with a soft, boyish face and auburn mustache curtaining his mouth. She pulled herself up to her full height and emptied her face of expression, wanting to appear as soldierly (and manly) as possible, and wondered what these men saw when they looked at her.
McClellan and the other generals, Samuel P. Heintzelman and Thomas F. Meagher, questioned and cross-questioned Emma about her views of the rebellion and her motive for wishing to “engage in so perilous an undertaking.” She would be going undercover, wearing clothing other than her military uniform, so if the Confederates caught her, they would treat her not as a prisoner of war but as a spy, and hang her as they did Timothy Webster.
Emma cited her strong Christian faith and her belief that slavery was against God’s will. Next came the easy part, a test of her skill as a marksman. She was most nervous about the final phase, a physical examination. She recalled her first medical exam with the army, when the doctor merely measured her height and shook her hand, and worried that it might be more thorough this time around.
This doctor, fortunately, focused mainly on her head, both internally and externally, a strangely intimate blend of psychoanalysis and scalp massage. With the doctor’s fingers kneading her skull, she answered dozens of queries about Frank Thompson, even venturing into the years before she became him. The doctor stretched a measuring tape from ear to ear and sketched a rough diagram of her head, estimating the development of various regions of her brain. She silently prayed that her head did not betray her sex; phrenological studies on women often concluded that their organs of “adhesiveness,” cautiousness, and procreation were so prominent as to elongate, and even deform, the middle of the back of the head. The doctor poked and prodded with his caliper and scratched notes on a pad. Emma felt stifled inside her frock coat, drops of sweat sliding down between her breasts. He determined, finally, that Frank Thompson indeed had the head of a man, with “largely developed” organs of secretiveness and combativeness. Emma acted as though she’d expected to hear as much, and took the oath of allegiance.
She had three days to prepare for her first mission: slip into Yorktown disguised as a slave and determine the number of Confederate troops stationed there, and the strength of the fortifications. The request was not unusual; spies on both sides used costumes and props and even handicaps, real or feigned, to deceive the enemy. There was a sudden proliferation of newsboys, actors, peddlers, doctors, and itinerant photographers, all of whom had a natural pretext for passing through the lines. Lafayette C. Baker, the Federal government’s chief detective and a professional rival of Pinkerton’s, wandered around rebel camps with an empty camera box. A Confederate spy named Benjamin Franklin Stringfellow capitalized on his slight figure and delicate features by dressing as a woman and frequenting Northern balls, gleaning information about Ulysses S. Grant from his dance partners. One of Pinkerton’s men, Dave Graham, feigned stuttering and epileptic fits as he wandered in Confederate territory, pretending to be a peddler. John Burke, a rebel scout for Generals Beauregard and J. E. B. Stuart, went undercover by removing his glass eye. Another Confederate spy, Wat Bowie, donned a homespun dress and scoured his body with burned cork, posing as a slave girl so convincingly that he fooled the Union detectives on his trail. Emma recognized the irony of her mission, layering a temporary disguise over the one she could never remove.
In the morning she set out for Fort Monroe to gather the elements of her disguise: a plantation-style suit, purchased from the contraband camp; a black wool wig from the postmaster (she explained that it was for “reconnaissance business”); and a vial of silver nitrate from the hospital medical supplies. A barber sheared her curls. She darkened her head, face, neck, hands, and arms; donned her suit and wig; and returned to camp near Yorktown, where everyone believed she was a contraband in search of work: “I found myself without friends—a striking illustration of the frailty of human friendship.” Nonetheless she was relieved; if the disguise fooled her comrades, she would certainly go undetected by the rebels. Staring at the mirror, she barely knew herself. She spent an hour practicing Negro dialect and picked a new and temporary name, “Ned.”
That evening, after the bugle call signaling lights-out, Emma filled her pocket with hard crackers, loaded her revolver, and hid a pencil and folded squares of paper under the inner sole of her shoe. She passed the Union guards outside Yorktown and walked as quietly as she could, at one point coming within yards of a Confederate sentry without being observed. She thanked heaven for her good luck, stretched out on the cold wet ground, and waited for morning.
At sunrise a group of slaves passed by, returning from bringing breakfast to the rebel picket lines. She followed them to camp, where they were ordered to work on fortifications, but she had neither tools nor any idea what to do. A young Confederate officer noticed her confusion and approached.
“Who do you belong to, and why are you not at work?”
“I dusn’t belong to nobody, Massa,” Emma replied, adding that she had always been free and was heading to Richmond to find work. The officer nodded and called for the overseer. “If he don’t work,” the officer said, “we’ll tie him up and give him twenty lashes just to impress upon his mind that there’s no free niggers here while there’s a damned Yankee left in Virginia.”
Emma thought of the fugitive slaves back at the Union camp, falling to their knees when they realized they were free.
The overseer furnished her with a pickax, shovel, and wheelbarrow. Emma watched the other slaves and followed their lead, pushing a load of gravel—the smallest she could get away with—up a narrow plank to the parapet. It was an arduous task for even the strongest man, each hoist of the shovel and stab of the ax grating against her skin, and by dusk she was raw from wrists to fingertips. If she wasn’t able to work at all the next day, the rebel officers would discover her deception. An idea struck: she paid a fellow slave to switch places; she would carry water for the troops while he built the fortification.
She took advantage of her new position, roaming freely about the camp, occasionally ducking behind a tree to sketch fortifications and jot down the number of mounted guns, 151 in all: three- and four-inch rifled cannon, thirty-two-pounders, forty-two-pounders, eight- and ten-inch Columbiads, nine-inch Dahlgrens, ten-inch mortars, and eight-inch siege howitzers. Lingering with one brigade, she overheard snatches of talk about the arriving Confederate reinforcements and was thrilled to glimpse Robert E. Lee. The men whispered that the general had come to inspect the Yankee fortifications, and that he had pronounced it impossible to hold Yorktown after McClellan opened his siege guns upon it. Another rumor claimed that the Confederates planned to evacuate Yorktown, the final piece of intelligence Emma needed. She had to return to her own camp before someone realized she was not what she seemed to be.
For the next two days Emma carried water, listened, and waited for a chance to escape. She was losing her disguise. Her scalp itched, her wool wig shifted askew, the silver nitrate peeled away to reveal patches of pale flesh. One slave studied her quizzically and joked to another: “I’ll be darned if that feller ain’t turnin’ white.”
She panicked and fumbled for a response. “Well,” she said, “gem’in I’se allers ’spected to come white some time; my mudder’s a white woman.” While they laughed she backed away, one foot behind the other, until she scuttled out of sight.
Early that evening she was among a group of slaves sent to deliver dinner to the rebel pickets. She walked down the line, dropping salted beef on tin plates, ducking minié balls shot by Yankee pickets half a mile away. The other slaves returned to camp but she hung back as long as she could, taking a seat on the ground. No one paid her any mind until two boots stomped into view and a faint shadow arched over her, accompanied by a booming order: “You come along with me.”
Emma obeyed, following the Confederate sergeant to a gap along the line where a picket lay wounded. Another rebel officer squatted over him, hoisting a canteen to his lips. The sergeant pointed at Emma and said, “Put this fellow on the post where that man was shot until I return.”
The officer nodded, and the sergeant turned back to Emma, thrusting a rifle against her chest and advising her to use it “freely.” Without warning his hands rose and encircled her neck. He gave her a hard shake, thumbs pressing at her throat.
“Now, you black rascal,” he said, “if you sleep on your post I’ll shoot you like a dog.”
“Oh no, Massa,” she croaked, “I’se too feerd to sleep.”
There was a new moon that night and the sky was lightless. The air turned dense and gave way to rain, drizzle becoming a downpour. Her color washed away, feature by feature, layer by layer. She heard a rustling noise, the rebel pickets taking cover behind the trees. Now.
Gripping her rifle—she was not going to lose that prize—she sprinted toward the thick forest dividing the two lines. As she neared Union territory, she pulled back, recognizing the absurdity of her situation: she was now in more danger of being shot by her own pickets than by the enemy. She waited for hours until a speck of sun appeared, flashed the Union sign, and stumbled back to where she belonged.
She gave McClellan her sketches and told him that the Confederate troops numbered 150,000, a third more than even the general had believed, and five times as many as there actually were. Such an inflated estimate was common among novice spies; even Pinkerton, for all of his success in foiling assassination plots and arresting traitors, knew little of war or warfare or how to gauge enemy strength, and sent out agents as untrained as he, even relying on observations from escaped slaves. The cautious McClellan was always eager to accept estimates of Confederate strength that confirmed or exceeded his own calculations.
Emma also relayed the most vital piece of intelligence: the rumor that the Confederates planned to evacuate Yorktown to defend the entrenchments around Richmond. Although others (including a slave who escaped at the same time as Emma) reiterated this claim, both the general and Pinkerton were dismissive, believing that the enemy intended to hold Yorktown at any cost.
But on this point she was right. Three days after she returned to camp, at two thirty in the morning, General Magruder and his rebel force fled, heading northwest toward Williamsburg. They had spent a week preparing for their departure, dismounting their guns, filling wagons with ammunition and provisions, and transporting 2,500 of their sick and wounded to hospitals in Richmond. When Union troops moved through, several men were killed by sub-terra explosive shells—an early version of land mines—hidden in the ground. Tents were left standing, with caricatures of Yankee soldiers scribbled on the canvas. They discovered several letters lying unfolded on a table. One was addressed to Abraham Lincoln, another to “The First Yankee Who Comes,” and the last to General McClellan:
You will be surprised to hear of our departure at this stage of the game, leaving you in possession of this worthless town. But the fact is, McClellan, we have other engagements to attend to, and we can’t wait any longer. Our boys are getting sick of this damned place . . . so goodbye for a little while.
The Union army was exhilarated by the news, which, Emma wrote, “spread throughout the Federal army like lightning; from right to left and from center to circumference the entire encampment was one wild scene of joy.” Jerome Robbins also noted the “unequalled excitement.” In a letter to Washington, McClellan characterized the retreat as a Union victory, declaring that “our success is brilliant & you may rest assured that its effects will be of the greatest importance. There shall be no delay in following up the rebels.” Despite McClellan’s bravado, he had no strategy for an organized advance. He improvised a pursuit with his cavalry and five divisions of infantry, including the 2nd Michigan, ordering them to “leave, not to return.”
Emma and her comrades were at the end of the force chasing Magruder’s rebels, marching through endless rain, the roads a perfect sea of sludge. They were encased in mud to the waist, tripping and tumbling headlong. With each step the battle roared louder, the crash of musketry reverberating through the woods, horses rearing, trees plunging. Rebels sent spray after spray of bullets into the advancing ranks, but still they charged forward through ditch and mire, loading and firing as they went, bodies dropping at Emma’s feet: “There was plenty of work for me to do here, as the ghastly faces of the wounded and dying testified.”
Orders came at her from all directions: Go to the front with a musket in your hands. Mount your horse and take an order to this general. Grab a stretcher and help carry the wounded from the field. At one point she saw a colonel fall and rushed over to him. Another “poor little stripling of a soldier” followed to assist. Together they carried him through a hail of bullets and set him down by the surgeon’s feet, lingering long enough to see if the wound was fatal. The surgeon opened the colonel’s shirt and found no holes, no blood. He examined him piece by piece—not even a scratch to be seen, and yet the patient seemed in too much pain to speak.
The surgeon stood and said, “Colonel, you are not wounded at all. You had better let these boys carry you back again.”
The colonel sprang to his feet, indignant. “Doctor, if I live to get out of this battle I’ll call you to account for those words.”
The surgeon leaned in close. “Sir,” he said, “if you are not with your regiment in fifteen minutes I shall report you.”
Emma backed away in disgust, “mentally regretting that the lead or steel of the enemy had not entered the breast of one who seemed so ambitious of the honor without the effect.” In the future she would determine whether a man was wounded before she moved to help him.
The hours passed and the rain came harder, drenching the living and the dead. Some lay on the ground, fully alive but helpless, their legs and arms too chilled and cramped to move. Emma made countless rounds from the front of the lines to the surgeon’s tent and back again, sinking under the weight of her stretcher, the mud suctioning her boots. Watching a young surgeon perform an amputation reminded her of unskilled hands preparing a turkey: “It was his first attempt at carving and the way in which he disjointed those limbs I shall never forget.” It had been a bloody day for the 2nd Michigan, with 17 killed, 38 wounded, and 4 missing, and even bloodier for the 5th Michigan, which lost 170 men. Both sides claimed victory in the Battle of Williamsburg, General McClellan calling it “brilliant” and the Confederates believing they had delayed the Federals, allowing their own army to retreat toward Richmond.
All told, more than 2,200 Union troops and 1,600 rebels lay scattered in heaps, the wounded and dead from both sides entangled in ravines. The dead lay in all postures, but mostly on their backs, heads tilted, mouths slightly open, one hand placed over the wound. One man remained on his hands and knees, with his head shot off. Two men lay face-to-face, each with his bayonet through the other’s body. An endless chorus of moans drifted across the field. During the darkness of the night soldiers fetched water from the ditch, plunging canteens amid the piles of corpses. A captain from the 5th Michigan emptied out the balance of his canteen to discover that it was “quite red.”
The enemies called for a temporary truce to collect their soldiers. “It was indescribably sad,” Emma thought, “to see our weary, exhausted men, with torches, wading through mud to their knees piloting ambulances over the field, lest they should trample upon the bodies of their fallen comrades.” A friend from Michigan was among the seriously wounded, shot clear through the thigh. She spent the next two weeks in a makeshift hospital in Williamsburg, tending to Union and Confederate soldiers alike and contemplating her next visit to rebel territory—this time with yet another layer of disguise, a woman impersonating a man impersonating a woman.