Impossible Escapes: Civil War
Pauline Cushman: Tales of a Yankee Spy
6/30/2025 | 39m 37sVideo has Closed Captions
When an actress-turned Union spy is caught and sentenced to die—can she act her way out?
While deep behind enemy lines, in search of a Confederate General, stage actress-turned-Union spy Pauline Cushman is captured and sentenced to hang. With execution looming, can she use her acting skills to escape?
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Impossible Escapes: Civil War is a local public television program presented by NJ PBS and WLIW PBS
Impossible Escapes: Civil War
Pauline Cushman: Tales of a Yankee Spy
6/30/2025 | 39m 37sVideo has Closed Captions
While deep behind enemy lines, in search of a Confederate General, stage actress-turned-Union spy Pauline Cushman is captured and sentenced to hang. With execution looming, can she use her acting skills to escape?
Problems playing video? | Closed Captioning Feedback
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Learn Moreabout PBS online sponsorship(suspenseful music) (indistinct yelling) - [Man] The Yankees are coming.
The Yankees are coming.
Form a skirmish line.
Keep moving forward, forward, forward, forward.
Form a skirmish line.
Forward.
Keep moving forward, forward, forward.
(suspenseful music) - [Man] Fire.
(guns firing) (horse neighing) - [Man] Miss Cushman.
Come back, Miss Cushman.
(guns firing) (soft traditional music) (soft suspenseful music) - [Narrator] This is the story of one of the most unexpected escape artists of the civil war.
Her name was Pauline Cushman and her 1864 firsthand account of infiltration, capture and escape from behind Confederate lines is unlike any other passed down through history.
(playful music) - [Pauline voiceover] My object in this little work is not to seek mere notoriety, but simply to state in homely and truthful language, the plain facts of my experience in the secret army service as a federal scout and spy.
(suspenseful music) (guns firing) - [Narrator] Two brutal years of war have passed, and there is no end in sight.
- By the middle of 1863, the death toll is rising.
There are people living in the far North who are beginning to wonder what this is all for.
The United States still can't seem to bring this war to an end.
- [Narrator] But this is the year that will change everything.
The critical Union victories at Gettysburg and Vicksburg lie on the horizon.
And a third conflict known as the Tullahoma campaign will be fought between the armies of general Braxton Bragg for the Confederates and general William Rosecrans from the United States army.
This campaign will determine the fate of Tennessee.
- Middle Tennessee is important because it provides the rail access and the river access into the heartland of the Confederacy.
If you want to pierce the heart of the Confederacy, you have to get through the Confederate army at middle Tennessee.
(soldiers shouting) - [Narrator] A major battle is only a matter of time.
Fear and anticipation spread from Tennessee out to neighboring states like Kentucky, which is a Union state, but also home to many Confederate sympathizers.
- Kentucky was arguably at the crossroads of the United States between the North and the South.
- It is a state where there will be families literally fighting with each other because of their commitment, either to the institution of slavery or their commitment to the United States and all that it represented.
- [Narrator] Soldiers and spies on both sides are on the lookout for any possible advantage.
Enter a struggling 29-year-old actress and recent war widow known by her stage name Pauline Cushman.
- Miss Cushman.
- Yes.
- I believe you know these gentlemen.
- I do believe I do, yes.
- [Narrator] Cushman moves to Louisville to perform for a local theater.
- Louisville was a place, obviously it was under Union control technically, but many of the men of the state served in Confederate regiments.
- And I thought that you might want to join us at the tavern tonight, is that of interest to you?
- Oh, absolutely.
It'd be wonderful to have your company.
- And sometimes they would be off duty.
They would be hanging out in a place, you know, in a tavern, intermingling.
(indistinct chattering) - We'll see you tonight.
(soft music) - [Narrator] Cushman is a strong supporter of the Union, - Lieutenant.
- but in Louisville becomes acquainted with a pair of captured rebel officers released on parole.
- [Pauline voiceover] I recognized them as agreeable friends, apart from any political consideration.
- Miss Cushman, we do have a proposition for you.
We would like to propose you make a speech during your next play, all right?
- Oh.
- [Pauline voiceover] They proposed at first laughingly.
- You think we should tell her?
- [Pauline voiceover] And then seriously.
I would step forward in front of the stage and offer the following toast.
- All you gotta say is, Here's to Jeff Davis and the Southern Confederacy.
May the South always maintain her honor and her rights.
- Lieutenant (indistinct) - [Second officer] We're in mixed company.
- All right, Lieutenant.
- Well, that is quite a proposal.
Such a proposition would have to be made worth my while.
- Cushman, we're willing to offer you $300, all right?
Ma'am, ma'am, don't, don't laugh.
- $300?
- Don't laugh, we- - [Narrator] They are asking her to give a toast to the president of the Confederacy, Jefferson Davis.
In a time of war, the amount, some $6,000 in today's money - It's all yours.
- would be hard to pass up.
- If I say the speech?
- [Both] Right.
- Well, now, that is quite an offer.
- [Narrator] But being on Union turf, the stunt could cost her her career, even her reputation.
She reports the incident to the head of the local United States military police.
To her surprise, he is thrilled.
They were in the process of planning a big forward push.
The army is looking for people to send behind enemy lines and this toast could provide Cushman the cover she would need to pose as a Confederate sympathizer.
- Well, by agreeing to do this toast in front of an audience that's loyal to the United States, here she's standing up praising Jefferson Davis.
I mean, she makes herself incredibly vulnerable.
- Is everything all right?
- Uh, yes.
Just trying to remember all these new entrances and exits.
- Five minutes, miss Cushman.
- Thank you.
- [Narrator] It was now on Cushman to either deliver the performance of a lifetime.
- That'll be all.
Give me a moment.
- [Narrator] Or return to a life of relative obscurity.
- [Pauline voiceover] Armed and fortified, I commenced my new role that very evening, feeling satisfied that I could serve my country, perhaps importantly.
(playful music) - [Narrator] The house is packed.
Both her US army contact and her rebel acquaintances are in attendance.
- You're on, Miss Cushman.
(strings playing) (audience clapping) - Why sister, I see you finally arrived on time.
- I'm always on time, aren't I?
- Well, a little bird told me you're having a little trouble learning how to flirt.
- Me?
Flirt?
- Well, it's all about directing his gaze.
Whether you want him to look here, or here, or here.
(audience laughing) (playful music) (audience clapping) May I have my drink?
Thank you, sister.
Thank you so much for coming this evening to see our little ditty.
To Jefferson Davis and the Southern Confederacy.
May the South always have her honor and her rights.
(audience booing) - I don't understand what just happened.
- Miss Cushman, are you all right?
- Please, please leave me.
You can't just leave, you're under contract.
- Let's just get you out of this dress.
- Please, go.
- [Man] I don't understand.
- Please leave me.
- She was trying to do something that would serve her country ultimately in the end, but she was also adventurous.
She was daring.
She was somebody always seeking a role in this society, in a society that didn't give a white middle class woman very many roles.
- [Narrator] She is now seen as a rebel sympathizer.
And she is far away from any of her family or old friends.
She is the perfect spy.
Her first forays into the world of spycraft come in and around Louisville, leaning on her new found reputation.
She drinks and shoots pool with Confederates, sometimes dressing as a man.
Anything to tease out useful information.
- Spycraft in this time meant getting physically in the space of the enemy, getting to know them personally.
- Women were always involved in military conflicts and they are extremely important for the relaying of information, working as spies, and in some cases, even serving in the military in official capacities.
(bouncy music) - Good morning, Miss Cushman.
- Good morning, Colonel Moore.
- What do you know?
- Well, a brigade from Hardee's corp went through Shelbyville here recently.
- Hmm, you know which brigade?
- No, I didn't overhear.
- Anything else?
- Well, Bragg's forces also had a bout of cholera run through 'em about the same time.
- You know where?
- Uh, Liberty?
- Liberty Gap?
- Liberty Gap.
- Very good, Miss Cushman, very good.
- Thank you, Colonel.
- We'll be in touch.
- Yes, thank you.
- Thank you, Miss Cushman.
- Thank you.
- [Narrator] Her next mission will take her 175 miles south to Nashville.
Nashville is occupied by Union forces, but she is just a few miles to the Confederate lines.
Cushman next makes contact with Nashville's chief of army police, Colonel William Truesdale.
- Thank you.
- Ah, Miss Cushman.
- Colonel.
- Please take a seat.
- Thank you.
- Do you take tea?
- Oh, tea would be lovely.
Thank you kindly.
- How would you like to take a trip to see General Bragg?
(suspenseful music) - I would welcome the opportunity, Colonel.
- Good.
Now, there's a few things we need to review before we send you across enemy lines.
- So general Rosecrans is planning a campaign against Bragg, and he's not entirely certain where Bragg is entrenched and where the bulk of his forces are.
- [Narrator] The Confederate army has been in retreat.
Morale under Bragg, a notoriously temperamental general is low.
But Rosecrans doesn't yet have enough information to launch his next attack.
- [Christopher] Pauline Cushman was instructed to figure out where the forts are, where the troops are, and report back.
- Armed with a six shooter and some emergency medical supplies, Cushman is dropped off a few miles outside of town, far from the prying eyes of enemy Scouts.
- Thank you.
- Some of the dangers of being a spy included the danger of being captured, being executed for one's crime.
- You must take on the role of a woman searching for her brother in the Confederate army.
- I do have a brother, his name is William.
- Ah, let this to all appearances be the all absorbing object of your thoughts and affections, casually alluding, however, to your ill treatment by the federal officers in Nashville, thrusting you out of the city, alone and unprotected.
- And I didn't even have time to procure my baggage.
- And they didn't even allow you time to procure your baggage, good.
- Cushman's cover was a really smart cover because this was pretty common in the border states, for families like hers to be divided.
- Halt.
Who goes there?
- Please, I mean you no harm.
I've just been expelled out of Nashville and just looking for some respite.
- You're from Nashville, Ma'am?
- Yes, sir.
- [Man] Ma'am, would you like a cup of coffee?
- That would be most welcome.
- [Narrator] She will attempt to hopscotch from one military camp to the next, in an effort to ultimately get to General Bragg.
- Miss Cushman, you cannot nor will not make any memorandum or tracings of any kind.
Is that clear?
- Yes, Colonel.
- Good.
- Thank you so much.
- [Pauline voiceover] I was in a region of country wild and broken.
The road was shut in on either side with a dense growth of trees.
- [Narrator] At this point, Cushman is in a kind of no man's land.
She's beyond the protection of the Union army, but she isn't quite behind enemy lines.
She comes up to a river crossing where the retreating rebel forces had destroyed a bridge.
Cushman is a fairly skilled rider, but fording this river on her own would be difficult.
(soft music) - Help you with anything?
- Afternoon, ma'am.
The river's too high to cross.
Do you know a different ford where I might be able to get over?
- Benjamin.
Come here, this poor gal needs to cross the river.
- [Narrator] She stops in a nearby house, owned by Benjamin Milam for directions.
- You ain't gonna be able to cross the river till the morning.
But you look awful hungry.
Why don't you come on inside, get yourself some food?
You can leave her right there.
It's fine, Baker'll take care of her.
- Thank you.
I would just like to express my gratitude to you both, for your hospitality, and letting me stay here in your home.
I truly do hope to cross the river tomorrow and be back on my journey.
- It's awfully dangerous out there.
Why are you traveling alone?
- Colonel Truesdale.
He expelled me from Nashville for expressing my Southern sympathies.
If only they knew my brother, they'd be thinking long and hard about how they treated me.
- Your brother.
What division did you say he was a part of?
- Cheatham's division, last I heard.
William Cushman?
Have you heard any news of him?
- Not recently, but we support those boys.
Listen, you're welcome to stay the night.
It'd be our pleasure.
Thank you kindly.
- Absolutely.
- [Narrator] She and Milam speak into the night, trading stories.
- All right?
You really wanna stay away from this area- - Where are the Confederates again?
- [Narrator] She learns that he is a hard line secessionist, but plays the role of a Union sympathizer.
- They had no idea.
- [Narrator] To smuggle tea, sugar, coffee, and dry goods into rebel-held territory.
- And they don't even know I'm doing it.
- Them Union soldiers are dumber than a box of hair.
(laughs) - Really are.
- You know, the way that Benjamin Milam is depicted, he's kind of this immoral Confederate in the way he's willing to just take any US oath just to be able to get inside the lines and smuggle goods out.
- So this Confederate camp, that's where General Bragg is at.
- Mm hmm, yeah, right there.
- [Benjamin's wife] Benjamin.
You let that poor gal get some sleep.
- Well, you heard the lady.
Get some shut eyes.
So I'm gonna, I'ma go.
- [Amy] The two of them - And that's what you think.
share some qualities.
They're both trying to move across the lines and be deceptive in order to do so.
- [Narrator] The next morning, Milam agrees to have Cushman ride with his partner, J.W.
Baker, to look for Bragg at a rebel encampment in Shelbyville.
- This should about get you covered.
- [Narrator] But he wants something in return.
- Mr. Baker will take you- - [Narrator] Cushman agrees to sell Milam her horse for $100 in Confederate money, which she will use to cover her costs on her mission.
She can purchase it back when she returns.
Milam says he plans to travel the opposite direction to search for a neighbor's escaped slave.
Cushman begins an arduous journey to the Confederate camp in Shelbyville.
(soft suspenseful music) - Hello?
I was told that you are officer of the day and that you might be able to help me.
- Yes, I am.
How can I help you?
- Yes, you see, I am looking for my brother, Lieutenant William Cushman.
I was hoping that you might be able to help me find my brother.
If he wasn't here in the camp, that you might know his whereabouts.
- I don't recognize that name, but what, maybe if we take a walk around the camp, you'll see him and you can recognize.
- Oh, I'd be forever grateful.
Thank you.
- I'd be happy to give you a tour- - [Narrator] Cushman doesn't waste any time searching for Bragg, and she claims her brother.
She worms her way into camp life.
- So how many troops do you have?
- [Narrator] Making notes and sketches of what she sees against orders.
- [Pauline voiceover] Arriving at Shelbyville, I learned that Bragg was not there.
And no one could tell me precisely where he had gone.
- [Narrator] What Cushman would've found in the Confederate camps is an army suffering through an incredibly wet and muddy spring, thin food stores, but a very robust collection of horses, information which would've been very interesting to general Rosecrans.
She does not however, find General Bragg.
- I can imagine.
- [Narrator] Frustrated in her attempts to find the general, Cushman looks for an exit out of Shelbyville.
Wherever Cushman goes, it seems she puts young soldiers under her spell.
- I didn't hear you.
- Hello, Lieutenant.
- Muah.
- So- - She enjoyed her work and Confederates enjoyed working with her.
- Good to see you, miss Cushman.
Well, here, can I get you a drink?
- Oh, actually I am the one who comes bearing gifts.
- And even though she was instructed not to draw attention to herself, it happened anyways.
- Don't ask me how I procured them.
- [Man] Oh wow!
- A lady must have her secrets.
Have things been relatively quiet around here these days?
- This Confederate engineer who is sketching out and designing these fortifications on paper.
And she gets a little excited.
- Rather difficult trying to find my brother.
I couldn't help but wondering, if a man of your station might perhaps write me a letter that would make it easier for me to pass from one line to the other in search of William?
- I think I can write you that letter.
- I'll be forever grateful.
I trust to return soon.
I plan to take an engagement at a theater in Louisville.
- Oh, you leaving us so soon?
- I shall return.
Thank you so much.
I will not forget you.
Keep your head down.
- She sort of forgets her orders or defies her orders.
You know, she's only supposed to gather information, which does not mean written documents.
It means simply listening and talking and bringing the information back from memory.
- She again breaks a promise made at the outset of her mission.
- Nor will not make any memorandum, is that clear?
- So in her mind, this is a great find, but that's where she probably overstepped a bit.
- [Narrator] She now has even more evidence on her that she has been spying.
And captured spies didn't typically make it home alive.
(Horse neighing) With every day that passes, anticipation along the front lines is building.
The Union's general William Rosecrans is making final preparations to attack Bragg's weakened army.
With an attack on the horizon, Cushman has just one stop to go before reconnecting with her Union contacts in Nashville.
She has driven back to Benjamin Milam's where she will attempt to retrieve her horse.
- Mrs. Milam, so good to see you.
- Benjamin hadn't returned yet.
Come on up to your old room.
- I thank you.
Things are well?
- Well.
- The next morning Cushman announces her intention to return to Nashville.
- [Pauline voiceover] It was quite evident to me that Milam was secretly alarmed at the idea of my return to Nashville.
- [Narrator] Her story is that she needs to retrieve her bags, but in truth, she has completed her mission and is eager to deliver her intelligence.
- [Pauline voiceover] It may be remembered.
He had disclosed the secret of his smuggling.
- I'd like to buy my horse and saddle back now.
- [Pauline voiceover] And now that I seemed determined to go back, - We'll see about that.
- [Pauline voiceover] he feared that his guilt might be made known to the Union authorities.
(bouncy music) - [Narrator] In an effort to cover his own tracks, Milam slips out of the house and sends word to the local rebel scouts about Cushman.
(Horses neighing) (indistinct yelling) - Is this the one?
- Yeah, that's her, get her out of here.
- Pauline Cushman, you are under arrest.
- There must have been some sort of misunderstanding.
- [Narrator] She's accused of crossing Confederate lines without permission.
- Please, listen to me.
- Come on.
- There must be some misunderstanding.
- She's a prisoner.
- [Pauline voiceover] Benjamin Milam betrayed me without having any evidence against me, but feared that I would expose him if I was allowed to reach Nashville.
- [Narrator] Cushman is captured and taken to the head scout who plans to take her to General Nathan Bedford Forrest.
(soft music) In this part of Cushman's story, she is handed off multiple times and treated, it appears, with kid gloves.
- Well, even as these military officials are seeing women doing some pretty daring things like espionage, they still harbor some reticence about treating these women like a man.
- [Narrator] They seem to let their guard down around her, giving her numerous opportunities to eavesdrop.
- No, he doesn't need any more of that.
But I do.
- [Narrator] Cushman is on the lookout for someone she can trust.
- Don't you stray too far, miss Cushman.
- Don't you worry, I'm just to the privy.
I'll be right back.
Excuse me, excuse me.
Will you do something for me?
You know where I come from, don't you?
- Up north, right?
- Here's a $10 greenback all for yourself, if you will but go up the road at peace and come back shouting at the top of your lungs that the Yankees are coming.
Do it at dusk.
- Yes ma'am.
- So when the civil war breaks out, every person in different ways is going to be thrust into a war for their survival.
It was never limited to those in uniform.
Enslaved people who are not even seen as people, they are well aware of how to use the system and the societies that oppress them to their advantage.
And they understand how integral they are to war efforts, but also how they can, even in oppression, help liberate others.
(ominous music) (man snoring) (suspenseful music) - The Yankees are coming.
(indistinct shouting) They're coming, the Yankees are coming.
Form a skirmish line.
The Yankees are coming, the Yankees are coming.
- [Soldier] Keep moving forward, forward, forward, forward.
Miss Cushman, come back, Miss Cushman.
Form a skirmish line.
Keep moving forward, forward, forward, forward.
(guns firing) Come back, Miss Cushman.
(guns firing) - [Narrator] Cushman is back on the run, but without an escort or a written pass, she'll need to talk her way through a series of rebel checkpoints.
- [Pauline voiceover] When I came up to be questioned as to how I, a woman, happened to be there at such an hour, whimpering and crying, I had a nice little story.
- Please, sir, my mother is very ill.
I need to cross.
- [Pauline voiceover] In a good canteen of the real stuff, we clinched the argument.
- My father lives down the way and my mother is very ill. - [Narrator] Repeating her story and sharing her canteen, Cushman works her way through checkpoint after checkpoint.
Having traveled more than 50 miles, she has just one more to pass through before reaching Union lines.
- Ho, who goes there?
- Please, Sir.
My father lives down the way and my mother is very ill.
I need to cross.
- Give the countersign ma'am.
- Please, Sir, I beg of you.
My mother's very ill.
I need to go and get supplies to help take care of her.
- I'm sorry, I'm under orders, Ma'am.
I need the countersign.
- Then perhaps some of the, I'll be joyful?
- I never drink, ma'am.
(drum beating) (horses neighing) - [Narrator] She's arrested again.
And it soon becomes clear that her notes and drawings have been discovered.
Her previous missteps have finally caught up with her.
Cushman is brought before Nathan Bedford Forrest, a wealthy Confederate General with a well known violent streak.
What he presents to her next puts Cushman in perhaps her most dangerous predicament yet.
- Good afternoon.
- You have certain documents about you and should their evidence prove you to be, as I suspect, a spy, nothing under heaven is gonna save you.
Now, I have no time to investigate your case, therefore, I'm sending you to General Bragg's headquarters.
- I can assure you, sir, that if I could get a letter to my brother, an officer in the Confederate service, that- - Enough.
Prepare yourself for worst, for hanging is not pleasant.
Kevin.
- [Narrator] Two days later, an exhausted Pauline Cushman is brought to general Bragg in Shelbyville.
But instead of arriving under cover, she arrives under suspicion.
What happens next will determine whether she lives or dies.
- Miss Cushman, your reputation precedes you.
I hear you've been all up and down our defensive line.
- Yes, and with good reason, I've been searching after my brother, Lieutenant William Cushman.
I haven't had word from him in months, and some of your men have been kind enough to let me pass so I can seek him out.
- William Cushman.
Well, I have a theory why you haven't heard from him.
He does not exist.
There's no William Cushman in my army.
Who sent you?
- Colonel Truesdale.
- [Bragg] What for?
- He kicked me out of the line in Nashville.
- Ms. Cushman, I have to inform you that there are serious charges against you.
- And if I'm found guilty of them, what will you do with me?
- You know the fate of spies, you will be hanged.
Colonel, take Miss Cushman back to her quarters.
- Punishments such as execution of a woman.
I mean, that is just one step too far.
This is not what you do to a woman in the society.
- According to her account, Cushman overhears her captors discussing Rosecrans's movements.
His army is just days from beginning their attack on Bragg's army of Tennessee.
But a more pressing issue for Cushman is her looming execution.
- Charges against you.
- Enough.
Nothing under heaven is gonna save you.
- You know the fate of spies, you will be hanged.
- [Pauline] Please, sir, I could get a letter to my brother.
- [Bragg] Who sent you?
- Colonel Truesdale.
- [Narrator] Cushman falls gravely ill, or at least appears to.
- To Jeff Davis.
- And the Southern Confederacy.
- [Narrator] With the Confederates unwilling to hang a sick woman, the longer they believe she is unwell, the longer Cushman will have to live.
- [Bragg] You will be hanged.
- [Narrator] Her condition persists for more than a week.
- [Man] Come back.
(horn blowing) - [Narrator] Just long enough for Rosecrans's troops to roll in and chase Bragg's army out of town.
- Saved.
- [Narrator] Cushman had escaped death.
- Thank God!
- [Narrator] And will soon find herself in the hands of the advancing United States army.
While the Union goes on to take over middle Tennessee, Cushman goes on to tell her story of adventures behind enemy lines, to military leaders and later readers and theater audiences across the country.
- [Pauline voiceover] Statements of every variety, some correct, and some erroneous have been made, respecting my strange and trying adventures behind the Confederate lines and my character of a federal scout and spy.
- So Pauline Cushman was a performer and throughout the rest of her life, as she told her story, she did so with a great deal of drama.
She was performing.
She continued to perform this role through the rest of her life.
- After her release from her captivity, she became a somewhat of a celebrity for her actions.
And she went on tour, speaking tours, she sold books.
She was managed by P.T.
Barnum.
- We can see in her story the way in which women took some pretty drastic, dramatic action to immerse themselves in the war itself.
No matter how much Pauline Cushman may have wanted to dramatize her story later, she was a really good actress.
Maybe that was the best, most effective acting of her life.
- Thank you so much for coming this evening to see our little ditty.
- [Pauline voiceover] The adventures I narrate have been but too real.
- That's her, get her out of here.
- [Pauline voiceover] My arrest, my condemnation to death by hanging, my rescue from the very jaws of death are absolute and solemn facts, which I at least can never forget.
(audience clapping) (soft traditional music)
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