It was awfully humid inside the Mozart Hall theater in Louisville, Kentucky, on one Saturday night in March of 1863. This border state was under Union control, and just a few hundred miles away, the Civil War was in its full and deadly swing. But inside the theater loyal Feds and rebel sympathizers sat side by side, tolerating each other’s company. All waited eagerly for the start of a traveling production of “Seven Sisters,” a musical about a septet of female demons that rise from hell to go sightseeing in New York City. It was the runaway hit of 1863.

The lights dimmed at a quarter past eight, but the seven sisters did not appear. Instead, one of the actresses slipped through the curtain, a Champagne flute in hand. Her name was Pauline Cushman, and she was beautiful, with an air of pomp one could not merely pretend to have.

“A toast!” she yelled. “A toast, ladies and gentlemen!”

The audience quieted below. Cushman cleared her throat, which allowed for a dramatic pause. Then — 

“Here is to Jefferson Davis and the Southern Confederacy,” she said, loudly and deliberately, with all of the stage presence in the world. “May the South always maintain her honor and her rights!”

Cushman, without ever cracking a smile, thrust the glass of Champagne up to her lips, chugged it down in a gulp, and waited for her applause. The hall was so still that the front-row patrons could hear her swallow.

The actress ducked behind the still undrawn curtain while guards, eavesdropping from the lobby, immediately swarmed the hall. To toast to the Confederacy in a Union theater! Surely she should be arrested immediately.

At the time, nobody knew that Cushman had been paid a hefty sum for this rash act. This was her first step in becoming a Civil War spy — maybe not the era’s most useful spy, but certainly a spy with a great story to tell.

*   *   *

No stranger to provocation, Cushman had traveled to Louisville to avoid mourning her first husband, who had died in Cleveland a few weeks earlier. He was a musician she’d met while working a theater gig in New York when they were both twenty. The two got married in New Orleans in a hall filled with friends (all “loud, theatrical people,” witnesses recall), but soon after they relocated to Cleveland, where Charles’s parents and brother resided. As Pauline kept busy with theater work, her husband enlisted in the Union Army and served as a member of the military band.

According to the biography Pauline Cushman: Spy of the Cumberland by historian William Christen, Cushman was an avid newspaper reader, and read with interest about women who had been discovered dressing up as men in uniform in order to help war efforts. She also noticed that there seemed to be no consequences if they were caught — for the most part, at least in Cleveland, the women dressed in uniform would be simply asked to go home.

She was excited by the idea of joining the Army. Since her childhood she had been drawn to adventure — her father was a merchant in the settlement of Grand Rapids and Pauline spent a lot of her free time as a child playing with the children of local Ottawa tribes. But there was no way Pauline would ever be able to pull off such a thing while married to Charles. For the year that Charles was enlisted in the Army, she kept tabs on these soldier-women from afar, wondering if one day she would be lucky enough to find herself in the middle of an adventure as exciting as the war.

A year after he enlisted, Charles died an awful death from complications that arose from acute diarrhea. Although her in-laws expected her to mourn for a year, Pauline could manage only two weeks. Leaving her two young children with them, she took a steamboat alone down the Ohio River in search of theater work that would keep her occupied — preferably work that would lead her to her dream job of working for the Union Army.

Upon arrival in Louisville, Pauline Cushman moved into a boarding house owned by two rebel officers by the names of Colonel Spear and Captain Blincoe. The pair had recently been POWs but were now on parole. They took a quick liking to this charismatic young actress, whose soft brown hair and porcelain skin were rhapsodized about in Ferdinand Sarmiento’s sensational nineteenth-century biography, Life of Pauline Cushman.

“Her form,” Sarmiento wrote, “is perfect — so perfect that the sculptor’s imagination would fail to add a single point, or banish a single blemish. [Cushman] resembles in mould the marble efforts seen in the great art-galleries of Europe.”

It was after Cushman’s second-to-last performance of “Seven Sisters,” as she and her two new friends were having a laugh and some drinks in the common room of the boarding house, that Captain Blincoe approached her with a proposition.

“Miss Cushman, suppose you drink a Southern toast tomorrow evening, and see what effect it will have upon the audience,” Blincoe said.

Cushman laughed it off as a ridiculous idea until Colonel Spear jumped in with an offer she couldn’t refuse. “Even for three hundred greenbacks?” Spear asked.

Three hundred greenbacks. That was a lot of money for an actress. Cushman told the men she would think about it, before rushing to Colonel Moore’s office at the Union Provost to ask for his opinion. Colonel Moore was a kind, gentle man who served as Louisville’s provost marshal for the Union. Might this be her ticket in to the Union Army as a spy?

According to Sarmiento, whose biography was approved by Cushman herself, her conversation with Colonel Moore went like this:

“Miss Cushman,” he said, “you have assured me of your love for the Union, and your earnest wish to do nothing but what is loyal and just, nor have I any doubt of your patriotism; but I must remark one thing, and that is, that we are often compelled, in the furtherance of our loved cause, to do things which are repulsive to us.”

“Well, sir?” asked Cushman.

“Well, I advise that you drink this rebel toast, as proposed. I request you, in the name of that country which you love so dearly, to drink this toast.”

Without really saying it, Moore was hinting that pretending to be loyal to the Confederates could prove to be beneficial for the Union later on. Without really saying it, that was what Cushman was hoping would happen.

Although she wasn’t arrested after her $300 toast, the theater owner had no choice but to fire her. But the job meant nothing to Cushman. She had plans to move on to bigger and better things — namely, spydom.

Cushman remained in Louisville for three weeks following the toast. Unionists refused to talk to her after her seemingly sudden change in sentiments, and she now had no friends save for the secessionist sympathizers, all of whom were suddenly smitten with her. It was time to move on. She decided to take a railcar to Nashville, where the chief of Army Scouts and Espionage for the Union was stationed.

*    *    *

The political climate in Nashville was far different than in Louisville — Nashville was under occupation by Union troops, and the tension between the sympathizers and the Unionists was palpable everywhere. Sarmiento describes the secession sympathizers of Nashville as “demented creatures.”

“Without the courage to seize the spokes of the great wheel, they smoothed the path down which they fondly believed it must pass over; oiling, with their snake-like tongues, first this, then that difficult passage, until the slime of their treacherous venom should pave the path for the destruction of the company,” he wrote.

Cushman secured an engagement at the New Nashville Theater, on the strength of a recommendation from her old boss in Louisville, who wrote that she was “a good looking woman and an accomplished actress [who] will talk secesh.”

On stage Pauline was received warmly by both Union and Secessionist audiences. The Union papers remarked that she was a “magnificent specimen of woman — rebel or not.”

William Truesdail, the chief of Army Scouts and Espionage in Nashville, was a kind, charitable person who gave money to the destitute and empathized with women who were caught posing as men in uniform — he was, in short, a ladies’ man. So Cushman and Truesdail got along well from the beginning. She had not been in Nashville long when he asked her to continue serving the federal government as a spy. Clutching a small American flag to her heart, Cushman took an oath of allegiance to the Union cause, kissing the stars and stripes while repeating the last line of the oath over and over again: “So help me God! So help me God!” Once the formalities had been attended to, Truesdail laid out his plan.

Cushman was to impersonate a Southern lady searching for her brother, a missing Confederate soldier named “Asa Cushman.” To win sympathy from the men in grey, she would complain of poor treatment at the hands of federal soldiers, who had forced her out of Nashville without belongings or baggage. The Confederates were always on the lookout for Union spies, and Truesdail warned her not to ask questions about anything but her imaginary brother, and never to write anything down. Her task was simply to get behind Confederate lines, find out what she could and report back to him.

“Are you sure this will work?” Cushman asked, trying not to show how terrified she was at the prospect of traveling through the South alone in search of someone who didn’t exist.

“Yes,” he replied. “As a consequence of your attractive personal appearance and modest demeanor, you will have many attentions paid to you by generals and staff officers. Accept all these invitations but with some hesitancy and seeming caution as to the propriety of such excursions.”

Before leaving Nashville Cushman was given a six shooter, bullets and small packages of quinine and needles — offerings for the military personnel she’d encounter. On her way out of the city she stopped at the house of Benjamin Milam, a smuggler loyal to the Confederacy.

It was Cushman’s first chance to try out her disguise. She approached Milam’s wife, crying, “All I have in the world I carry on my back — my wardrobe, my jewels — everything!” She described her brother Asa in detail, about how she was moving south in order to find him. Milam bought it, giving Cushman shelter and a couple hundred dollars in Confederate money for use on her trip. She was an excellent actress — this was going to be a breeze.

*    *    *

Her target was General Braxton Bragg, the direct military advisor to Jefferson Davis, whose headquarters was located in Shelbyville, Tennessee. She planned to contact Bragg, explain the search for her missing brother and get his permission to move freely behind Confederate lines. But when she reached Shelbyville, Bragg was not there, and no one would tell her where he had gone.

In Shelbyville, Cushman stayed at the Evans House in the center of town, where she became friendly with one of the head Confederate military engineers who was also staying there. As Cushman was wont to do, she stayed up late into the night with her new friend, chatting and playing cards. The engineer was so taken by her looks and charm that one late night he invited her back into his room for drinks. When Cushman searched the room she noticed something astonishing.

The engineer had forgotten to hide a few important papers sitting on his desk — papers that were filled with sketches of Confederate defense fortifications. When the engineer was distracted, or too drunk to be paying attention, Cushman snatched up the drawings and left the room with them. She studied the notes she’d stolen from the Confederate engineer, and even took the liberty to sketch what she believed would be the Confederate Army’s next moves. Cushman was conscious of the fact that even taking the papers from the engineer’s room was a stupid thing to do, but the excitement of such a perfect discovery so early in the game — to her, it felt a bit like fate.

While Cushman was in Shelbyville awaiting Bragg, the Union Army in Franklin hanged two Confederate spies, and issued an order stating, “All persons found within our lines who commit acts for the benefit of the enemies of our country will be tried as spies or traitors, and, if convicted, will suffer death.” The Confederate Army was sure to respond in kind. The consequence, should Cushman be caught now, would be death.

*   *   *

Deciding she would be safer on the road, Cushman left Shelbyville, bolting from town to town in a set of stolen boy’s clothes, searching desperately for Bragg or Union soldiers who could take her home. Along the way a message reached her offering a job at a theater in Richmond. A job back on the stage at this point seemed a much easier and less stressful way to make a living. But first, Cushman needed to get back to Nashville to get her luggage.

Without a pass from Bragg or help from the Union Army, the only way back into Nashville was to be snuck in, and so she returned to Milam, the smuggler who had been so kind to her at the start of her mission. But the atmosphere at his house had changed. Worried that she would inform on his smuggling operation, he refused to help her back into the occupied capital, and turned her out into the night.

Cushman took refuge at a nearby farmhouse, lying to the farmer with very real tears. She had not been there an hour when four Confederate soldiers appeared at the door. They arrested her and brought her to General Bragg, who had been in Shelbyville all along.

In her hurry to leave Milam’s, she had left behind her few belongings — including the sketches of the Confederate fortifications. Those few scraps of paper were all the evidence Bragg would need to hang the Union spy.

*    *    *

General Braxton Bragg was notorious for two things: being a bully and hating spies. After shutting the door behind him in his office, he stared at Cushman with a look of utter contempt. It was she who spoke first.

“If I am found guilty, what will you do with me?” Cushman asked Bragg, her lovely round eyes open wide with terror.

“You know the fate of spies,” said Bragg. “You will be hanged.”

“General, I don’t think I would look well dangling at the end of a rope. If I must die, I hope you will allow me to choose the manner of my death.”

“You will,” Bragg repeated, “be hanged.”

After a four-day trial, Cushman was found guilty and — as Bragg had promised — sentenced to hang. While in jail, she fell sick with a mysterious illness, brought on by a combination of stress and exposure to the Tennessee wilderness. Exhausted and feverish, she was denied treatment by the Confederate couple who housed her while she awaited death. As she grew sicker, Union troops led by future President James Garfield slowly advanced towards Shelbyville.

In late June, Cushman was moved to a doctor’s house, in hopes that she would recover enough to be hanged. The man tasked with transporting her professed his love to her during her jail time, and when she was so sick she couldn’t lift her head, he asked her to marry him. He was carrying her onto the street in a stretcher when the Union Army rolled into town. She recovered from her illness at General Garfield’s side, and her near-death ordeal was plastered across newspapers throughout the Union.

The most famous photo of Pauline Cushman that exists is one in which she dons a garment laced with military decorations, wearing an affixed fake mustache and goatee. The uniform was said to have been a gift from the loyal ladies of Nashville.

This was the photo that would be used for the press when her acting career picked up again. This occurred the following year, when P.T. Barnum caught wind of her story, and decided to kick-start her national theatrical tour, “Miss Major Pauline Cushman, the Union Scout and Spy.”

The loyal Unionist’s gravestone lies in a cemetery in Arizona, which is where she retired in her old age, remarried, and changed her name to Pauline C. Fryer. As was the lady’s wish, her tombstone says nothing about her lifetime profession as an actress. It reads only “PAULINE C. FRYER—UNION SPY.”

*   *    *

Christina Drill writes poetry and nonfiction and lives in Brooklyn. She edits the literary magazine Pieces of Cake and is currently working on an anthology of memoirs about growing up in the American suburbs.