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SEASON 08 / EPISODE 05

The Spy on Death Row

This is the story of a woman who saw an opportunity to apply her acting skills to become a spy during the American Civil War.

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Worry nagged at her. She remembered the last words from her superior,

“Never take anything. If they catch you with evidence, you’ll hang.”

But with this battle plan, the Union forces could drive the Confederates out of Tennessee. She dismissed the voice in her head and quickly folded the map, sat down and unbuttoned her boot.

She heard men’s voices outside the tent. Her heart pounded. She shoved the paper deep into her boot and fumbled to secure only a couple of its buttons —just enough to hold the map in place.

She jumped up as a group of young Confederate officers entered the tent.

She flashed a charming smile, regained her composure and said, “Officers, I have news for the General.”

The men recognized her. She was the pretty actress with Confederate sympathies. Or so they thought.

The woman never expected to be a spy. She had always yearned for adventure and hoped acting would give her that. She was able to follow her passion for a while, but then life and family slowly started pulling her away. Her husband entered the war fighting for the Union but returned ill with dysentery. A few months later… he was gone.

Left alone with two children, the young widow knew she would need money to support her family. She left her children in the care of her in-laws and took an acting job in Union-controlled Louisville, Kentucky.

She hated being away from her children but loved the opportunity to act again. She put her heart into every performance and ended each night with a rousing toast to President Lincoln.

One night, after her performance, two paroled Confederate soldiers approached her. They offered her $350 to toast the Confederate president, Jefferson Davis, instead of Lincoln. She accepted the offer and, the next morning reported the bribe to the Union provost-marshal, Colonel Moore.

She thought he would arrest the men. But Colonel Moore surprised her and said, “Oblige the men. Make the toast.”

She was dumbfounded.

He went on, “I want you to convince them that you’re a Confederate sympathizer. They’d love to have a popular actress on their side. And they’ll introduce you to all their inner circles.”

The next night, she walked on stage, raised her goblet, and in a clear voice said, “Here’s to Jefferson Davis and the Southern Confederacy. May the South always maintain her honor and her rights!”

The audience was stunned. The Union supporters began booing and hissing. The Confederate dissenters joined the fray, cheering her on. The manager raced on stage and fired her on the spot.

On that night in 1863, she became an instant hero in the eyes of Confederate supporters. On that night, she began her career as a Union spy.

The Confederates introduced her to their inner circles. Within weeks, she moved to Tennessee and met Confederate militia officers. They all wanted to meet the actress who turned on the Union.

She posed as a camp follower and began feeding information back to the Union forces. It was useful, but not enough. She knew she needed to do more.

One night, she watched from the shadows as a group of soldiers headed to the saloon. She knew they would be there for hours. And once drunk, they would speak freely. A lady could never enter such an establishment — but a man could.

The next day she procured a man’s suit and put her acting skills to the test — it was her most important role to date. That evening, dressed as a young southern gentleman, she followed the group of soldiers into the saloon, bought them a round of drinks and peppered them with questions.

It worked. She learned intricate details of their upcoming troop movements.

She took more risks — going undercover, stealing documents and gaining access to more leaders. And she loved every minute of it.

That’s how she found herself in General Bragg’s tent, with his battle plans stuffed into her boot, charming the group of Confederate officers.

The officers encouraged her to reveal her news of the Union forces.

She saw a chance to escape. She insisted that she needed to tell General Bragg herself, knowing that he wouldn’t be back for hours.

But the major implored her to wait until he arrived.

Just then, the private walked into the tent and whispered something to the major.

Her pulse raced.

“Ma’am, I, uh… I’m not sure how to say this, but could you show me your… feet?”

She flashed a grin and said, “Why, Major! How impertinent!”

“I’m sorry, ma’am. But my private here thought he saw you… put something in there.”

Her heart sank. He had seen her. She giggled and said, “Sounds like your private wants a peek under my skirt, Major.”

The other officers laughed nervously, but the major never broke his gaze. “Please show me your feet, ma’am.”

Then the private blurted, “She stuck papers in her boot! Papers from the General’s desk.”

It was all over. The officers found the damning evidence and took her into custody — it had only been three months since she started her career as a spy. General Braxton Bragg tried her and sentenced her to death by hanging.

As her execution approached, she grew gravely ill — Her captors decided, ironically, to postpone her execution until her health improved.

Languishing in her cell, she thought to herself that it had all been worth it when she heard a volley of gunfire.

The Union Army advanced and forced the Confederates to flee, leaving her in the care of a physician.

When Colonel Moore came to see his bedridden spy, she popped off the bed and grinned.

Her final role had worked.

With her cover blown, her career in espionage ended. But not without glory. President Abraham Lincoln awarded the woman the honorary rank of Brevet-Major.

She then toured the country in a one-woman show, dressed in a Union uniform and fascinating her audiences with tales — some taller than others — of her undercover adventures.

She came to be known as… Miss Major Pauline Cushman.

Cushman’s call to purpose came disguised as a call to adventure. And it came with a price.

At a critical point in the Civil War, Cushman had to feign support for the enemy. Doing so cost her a paying job, friends, family, and reputation. She was forced to move behind enemy lines. But neither the risks nor the realities of war swayed her from stepping into the role of a lifetime.

Novelist Andre Gide said:

“Man cannot discover new oceans unless he has the courage to lose sight of the shore.”

Sometimes the new oceans to discover are those that lie within.

During her three-month tour as a spy, Pauline Cushman was injured and captured twice.

But only through her tour did she truly learn what she was capable of achieving.

And only through her adventures did her life take on a higher purpose.

Maybe there’s a new ocean for you to discover. And it’s just an adventure away.

That’s her story. What’s yours going to be?

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