What if I were to tell you
that the commander in chief of the United States had
an inner circle of trusted spies working just for him? Well, in 1778, such a
spy ring was established by Major Benjamin Tallmadge. It was made up of
mostly ordinary people. The group played a crucial role
in winning the Revolutionary War by providing critical
intelligence about the British and helping to expose
the most infamous traitor in American history. They were called
the Culper Ring. They were at the cutting edge
of espionage for their day, using invisible ink
and even publishing coded messages in newspapers. These guys were so
secretive, none of them even knew who the
other members were. In fact, Americans didn't even
know there was a Culper Ring until the 1930s. There's been a
lot of speculation about the first
American spy ring. This time, I know their story. And when it comes to
the greatest spy master in the United
States, the man who created what led to the CIA,
you won't believe who he is. [theme music] I'm Brad Meltzer. I've spent my life
collecting stories. The best include signs, symbols,
and codes, secret meanings that are hidden in plain sight. Some have become the
basis for my novels, but I've only scratched the
surface of what's out there. And now, History has
given me the resources to investigate the rest. This is "Decoded." BUDDY LEVY: If you're
looking at the history of American espionage and
the history of spy rings in this country, where else
would somebody go but the CIA? CHRISTINE MCKINLEY: Oh, my god. I can't imagine what Brad had
to go through to get us in here. He must know someone
who knows someone. SCOTT ROLLE: First time
I've ever been here. No experience like this. I've been all over the
world in the military, but this is the first time
at the CIA headquarters. So I'm really excited about it. It just is a place most
people don't get to go. BRAD MELTZER: Most people
think that the need for a spy organization grew out of the
desperation of World War II, but it's even older than that. The Culper Ring grew out of
the need for intelligence about the British
stronghold in New York City, and the group itself
remained unknown to history for more than a century. But their practices were used
in the design for the CIA and their predecessors, the
Office of Strategic Services, or the OSS. The origins of US
intelligence dates to the founding of the republic. In a sense, espionage is
as American as cherry pie. To understand where
the CIA came from, we still, in our
training courses, go all the way back to
the American Revolution and really the first spy
in US history, Nathan Hale. And there he is, ready to
say, I only have but one life to lose for my country. BRAD MELTZER: Nathan Hale
was a 20-year-old captain in the Continental Army
when he volunteered to sneak across enemy lines
and spy on the British. Unfortunately, Hale
was a terrible spy. He was captured and
the Brits executed him. Just before he died, he
uttered that famous line. "I only regret that
I have but one life to lose for my country." The thing is, some historians
say Hale never said it. It was a line from a
popular play back then. And the statue of him in
front of CIA headquarters? When William Casey
took over the CIA, it drove him crazy that there
was a Nathan Hale statue there. Nathan Hale was
a spy who failed. In Casey's eyes, the
statue should have been a member of the Culper Ring. BUDDY LEVY: What happened
after Nathan Hale's demise? The Continental
Army very quickly develops an amazing array of
techniques involving deceptions and double agents and
phony troop movements and a very sophisticated
network of agents based in New York City and
further out on Long Island. So you're talking
about the very origins of American espionage. DAVID ROBARGE: Exactly. Because it's so elaborate and
involves a lot of tradecraft techniques and technologies,
probably best if we head inside to the CIA Museum, and
we can talk about it and show you some
of the capabilities that the Continental Army
was using way back when. So you've got a museum
right here at the CIA. We call it the best
museum you've never seen. We've got a great museum. We're just not going
to show you anything. That's right. DAVID ROBARGE: The CIA
Museum has a great collection of tradecraft devices
that we and other services have used throughout our
history to encode and encrypt and conceal our writing. And those are techniques
that, though they sound really modern and sophisticated,
we can see being used back in the day of the Culper Ring. Much of the information was
written in code and cipher and concealed with invisible
ink or sympathetic stain, as they called it back then. Here's how the Culper
Ring actually worked. Members in New York City
reported their information to an operative who was called
Culper Jr. That information was then passed to a member from
Long Island, who came to town to get supplies for his tavern. And when he got home,
he'd pass the information to another member, whose
code name was Culper Sr. And he'd then decide what
information was important and pass it on to a fourth
member, who would paddle across Long Island Sound to
Connecticut, where the Army was holed up after losing
New York to the British. From 1778 to 1781, this was
how top secret information was relayed back and forth. DAVID ROBARGE: They
were volunteers. And then-- and this is
a key part to the ring-- nobody knows entirely
who everyone is and how it's all working. So if one guy's caught, no
matter what they do to him, he can't possibly-- DAVID ROBARGE: Exactly. It's all part of being able
to keep the ring completely secure. Is there an example you can
give us of where this ring actually had some success? DAVID ROBARGE: In 1780,
there are clear indications that the British are
mobilizing an attack force to greet an incoming
contingent of French troops. Now, this is only two
years into the alliance, and the French had been
stalwart friends of ours. But a military disaster
like that could have-- CHRISTINE MCKINLEY: Right. DAVID ROBARGE: --got them
thinking a little bit differently about the long term. Because of information
coming from Culper Jr., the Continental
Army gets this news. It sends out messages
through known British agents that Washington was going
to attack New York City. That disinformation got
to the British commander. He stops in midstride,
turns the whole army back to New York
City to counterattack against a Continental
Army that isn't there. CHRISTINE MCKINLEY: Isn't
coming at all, yeah. DAVID ROBARGE: And
French troops arrive in Newport, several
thousand of them, untouched. The members of the
Culper Ring were not men who looked for glory. These were ordinary civilians. They met in bars, alleys,
and secret locations all around New York
to pass information that was essential to the
Americans winning the war. Among these places was the area
around what is now Rivington Street in lower Manhattan. Buddy is there now to find
out more about the successes of the Culper Ring. WILLARD STERNE RANDALL:
I suggested we meet here on Rivington Street that's
named after this great spy that nobody in New
York City knew was a spy during the revolution. Rivington knew everybody
inside the Culper Ring. He worked and owned
Rivington's "Royal Gazette," a very pro-British newspaper,
which gathered news from all the loyalists and the
British officers, et cetera, and put it in the paper where
Washington and his officers could interpret it and
figure out what was going on. Talk about hidden
in plain sight. Spy-coded information going
out in the public newspaper? The British were
completely fooled. BRAD MELTZER: The key to the war
was control of the Hudson River and Fort West Point, which
was perched on the west bank. As long as we had that,
it meant the British only controlled half the river. And this was key
because if they were able to seize the
west bank, they could divide New England
from the southern colonies and choke our supply lines. West Point was also strategic
because it was situated at an S curve in the river. Boats had to slow
down to pass the area, and that meant enemy
ships were particularly susceptible to attacks there. So the British knew
to win the war, they had to take West Point. BUDDY LEVY: Sounds like you're
saying that West Point was the key to America's future. I don't think that's
any exaggeration. The British had tried
to fight their way up a few times before. They had ships all
over the river. But there was a chain across
it, for one thing, that would have stopped any British
ship from getting near West Point. A physical chain
across the river? WILLARD STERNE RANDALL: A huge
chain from Constitution Island to the West Point shore. BUDDY LEVY: So you
needed a serious pass to get up the river. Oh, you needed a total
pass to get past the river. And it could only come
from the commanding officer at West Point, who
happened to be Benedict Arnold, the greatest hero of the
Revolution up till that time. BUDDY LEVY: So what exactly
happened with Benedict Arnold? WILLARD STERNE RANDALL: Benedict
Arnold was seven years behind in his pay. And it all added up to him
saying, I've had enough. I'm going to get my money. And he began writing coded
messages to the British in New York City. You know you're the best at
something when your name become synonymous with it. And Benedict Arnold quite
simply means traitor. But that wasn't always the case. At one point, Benedict
Arnold was the greatest hero our country had ever known. The problem was we were
fighting a guerrilla war, and money was sparse. This gave the British just the
opening they were looking for. Arnold's plan was to sell
West Point to the British in exchange for 20,000
pounds, a fortune at the time. He was going to tip off the
British at the right moment to come up the Hudson, when
Washington, Lafayette, and all the American and French
generals were at West Point. Arnold would then very
lightly defend the fort and then surrender it, along
with Washington and all the generals, and the
war would be over. If Benedict Arnold had
succeeded in his plan, the American Revolution
would have collapsed. There would be no
independent nation. So how exactly was
Benedict Arnold exposed? The Culper spy ring was
putting together what was going on through a year and a half
of intelligence gathering that a high-ranking American
officer was about to go over, that it had to be
Benedict Arnold. As far as we can tell, the
Culper spy ring intercepted coded messages sent by
Benedict Arnold to John Andr , the head of British
intelligence. As brilliant as Arnold
was, it turned out he was no match for
ordinary American citizens. How did John Andr
finally get busted? WILLARD STERNE RANDALL:
He accidentally got caught by three fellows
who thought he had nice boots and maybe had some money. The men who captured
Andr turned him over to a subordinate, a man
underneath Arnold who was just going to send him to Arnold. And then Arnold would
be in the clear. Instead, Benjamin Tallmadge,
head of the Culper spy ring, was the next man to see John
Andr on his way to West Point and said, here's our man. Did Benjamin Tallmadge
get Andr to confess? WILLARD STERNE RANDALL: Yes. When John Andr admitted
to Tallmadge that he was on a spying mission, Tallmadge
sent the documents found in Andr 's boots to West Point. And Arnold saw them, didn't even
wait to kiss his wife goodbye, ran down to the river
with two pistols, and ordered his guards to
row him down the Hudson to the nearest British ship. He went to New York and
immediately started rounding up the members of the Culper Ring. He got a few. He got a few, but the
rest went into hiding. Spies in hiding. I like it. BRAD MELTZER: The Culper
Ring is, without question, the predecessor of both
the OSS and the CIA. But what amazes me most is just
how successful the Culper Ring was to us winning
the Revolution. You have to remember,
nobody back then truly knew who was
loyal to the crown and who was loyal to
George Washington. New York City, like today,
was filled with people who were playing all the angles,
so knowing who to trust was paramount. The adage "All is
fair in love and war" was coined in 1850
by an English writer, but it was just as fitting
in revolutionary America. By 1778, the colonies have
lost control of New York City to the British, and they're
holed up in Connecticut trying desperately to maintain access
to the Port of New York. The Americans know
that their only chance to retake the
island of Manhattan is if they get
better intelligence, so Major Benjamin Tallmadge
helps create a network of civilian spies, known
as the Culper Ring, to help provide insight
into the British plans. The ring operates in
and around New York, where Buddy, Mac, and
Scott are headed right now. Morning. Hi. We're expecting a
package for 1410. For 1410? My pleasure. - Thank you.
- Thank you. You're welcome. That's his book. It's the advance
copy of his new book. - Does he want us to read it?
- I don't know. Is it free? CHRISTINE MCKINLEY:
What's he doing? There's a blank piece
of paper in here. This has got to be more than
a shameless self-promotion for the book.
BUDDY LEVY: OK. There's nothing on here. Yeah, there is. Yeah, there is, because
you can see a tiny mark. - Like it's invisible--
- Yeah. - --ink or something?
- Yeah, yeah, yeah, yeah, yeah. That's not helpful. Mac, how would you check if
there's something on there? Well, the best way to speed
up a chemical reaction is heat. All right.
Who's got some matches? Heat it up. [inaudible] Oh,
he included matches? Yep.
Yep. OK. God, I hope I don't set
off any alarms in here. BUDDY LEVY: Do what she says.
- Just like that? OK.
Hold it there. SCOTT ROLLE: Nothing. BUDDY LEVY: Nothing's happening. I like the intrigue, though. SCOTT ROLLE: Yeah.
CHRISTINE MCKINLEY: Ooh, ooh. BUDDY LEVY: Oh. Whoa. It's working.
- Wow. Look at this. CHRISTINE MCKINLEY: The-- who
was the greatest American spy master of all time? Who was the greatest
American spy master-- - Greatest American spy master.
- Greatest American spy master. BUDDY LEVY: --of all time? No idea. Yeah. I would go Cold War.
Were there spies in World War I? He said we have
everything we need in here. I think so, yeah.
CHRISTINE MCKINLEY: [laughs] BUDDY LEVY: Well, OK.
There were spies-- Look, he's put a
little dedication for us. SCOTT ROLLE: [inaudible] CHRISTINE MCKINLEY: Go to 54
Pearl Street, New York, New York, to find the answer. OK. Yeah, OK. So we've got to go. SCOTT ROLLE: Let's
head over there. Keep the matches. God knows what else
he's going to do. BUDDY LEVY: Yeah. I'm sending the guys to
Fraunces Tavern, which is where the original idea
for the Culper Ring may have first been discussed. It's also the place where
President George Washington gave the nation's first
farewell address when he decided that two terms in
office were enough. Buddy, Mac, and Scott are going
to meet with someone who knows more about the
Culper Ring's methods than anyone else in history. And let me promise you, there'll
be no more product placement, except for the giant Porsche
the guys drive around in. Brad told me to expect you. Now, the answer to his question
is written between the lines. BUDDY LEVY: We better
just fire it up. This is how the Culper spy
ring used invisible ink to communicate with-- Oh, check it out. Look, look, look, look. BOTH: George Washington. How is that?
BUDDY LEVY: Come on. CHRISTINE MCKINLEY: He's
the first founding father. BUDDY LEVY: We think
of George Washington as an honest, noble gentleman. For somebody who
never told a lie, he stretched the truth a lot. You're telling
us he was a spy? He was a spy master. BRAD MELTZER: While Major
Tallmadge organized the Culper Ring, he did so at the direction
of General George Washington. And while many remember
Washington for his honesty, the future president knew
the value of covert info better than anyone. Washington had lost New York
City to the British in 1776, but he had loyal citizens
living in the city-- regular, ordinary people-- who were willing to provide
details of the plans of the entrenched Redcoats. That's who George
Washington relied on. And the Culper Ring was crucial
to Washington's plan to take back the key Port of New York. To do it, to pass
those messages, it was dangerous, so
the ring devised ways to move their secrets
in plain sight. Washington's favorite method was
to use white or invisible ink, and he'd physically
write between the lines of a normal letter, which
is where we get the saying, "read between the lines." He called it his
sympathetic stain, which is a horrible name,
but it was made using parasulphate and water. It was a chemical process. You write in one chemical,
called the agent, then the reader of
the letter paints it with another
chemical, the reagent. That way, you can't just
crack it with a match. And the solution was
supplied by Dr. James Jay. And let me tell you, these
guys knew what they were doing. To this day, the FBI and CIA
use invisible ink messages that are based on George
Washington's method. He set up many spy
rings, and the Culpers were one of the first. Wow. JOHN NAGY: And they used
invisible ink to communicate. So did they keep records
of how to decode this stuff? Here's the copy of the
Culpers' actual code book. BRAD MELTZER: Invisible
ink wasn't the only code used by the Culper Ring. Major Tallmadge came up
with a series of other codes that were all listed
in his code book. Only four copies of
the book were produced. Tallmadge had one
copy for himself. He gave General George
Washington another. And the Culper Ring leaders
were given the remaining two. The code was simple. The most popular
words at the time were all assigned a number. The word "signal" was 600. The word "lord" was 351. The members of the ring were
also given a similar code name. General George Washington's,
for example, was number 711. So this was a very
valuable document that people would die for.
- Extremely. Yes. BUDDY LEVY: And die over. CHRISTINE MCKINLEY: Wow. To think of the American
Revolution being this high-tech is very strange to me. JOHN NAGY: It is. This is the way it worked. BRAD MELTZER: What
I want to know is, how'd this group of
people move information from place to place so quickly? I mean, when it comes to
speed, horses and sailboats aren't exactly like sending
an email from a dummy Hotmail account. And most important, whatever
happened to the Culper Ring? Did they die off, or are
they still out there today? To this day, it may be George
Washington's greatest magic trick, creating a small,
covert spy ring made up of regular citizens who kept
their secret for over 100 years. These guys were the
grandfather of the CIA, and it shows you how smart
our founding fathers were. The ring's existence was hidden
for a century and a half, and these guys were so far
undercover that even death didn't reveal them. The true identities
of the Culper spies were hidden from the
history books for 150 years. You see, General Washington
didn't know who the spies were, and the spies didn't know the
real identities of each other. But they were
eventually discovered. Mac and Scott are in
the East Hampton Library to find out how. Gina, Scott and I are trying
to find out everything we can about the Culper spy ring.
- Uh-huh. And it's hard to find these
guys' identities because they were so well-protected. It seems like they were even
protected after their death. So how were they
discovered eventually? Eventually, the
identities were discovered through the diligence
of Morton Pennypacker. Mr. Pennypacker was a
local historian here in the East Hampton area, and
he mainly collected information having to do with
Long Island history. He was going through a
collection of papers that were discovered in the
Robert Townsend family home. They found an old
chest in the attic. It was filled with singed
letters, old documents, things of that nature. And this was very exciting
to Mr. Pennypacker because he discovered
a possible link to the identities of the
members of the Culper spy ring. How did he link it
to the Culper spy ring? They actually compared
Robert Townsend's letters that had been found in the
George Washington collection. They put them side
by side, and they were able to analyze the
handwriting that way. And they discovered
that, without a doubt, these were the same people. CHRISTINE MCKINLEY:
So the letters that George Washington had,
they knew were Culper spy ring letters. And they compared it to
the Townsend letters, and they're the same guy.
- Yes. That is correct. CHRISTINE MCKINLEY: Wow. SCOTT ROLLE: George Washington
himself did not even know the identity of the
members of this spy ring. And then here we have
somebody around the 1930s who finds some documents in an
attic and is able to compare them and find out these are the
people that were the members of the Culper spy ring. It's just incredible. CHRISTINE MCKINLEY: Who was
Townsend in the Culper spy ring? He was known as Culper Jr. [gasps] Culper Jr. That is Culper Jr. I actually have some examples
here of books that were kept by Robert Townsend himself. These are original documents. They're not copies. They weren't fabricated. These are his actual
account books. SCOTT ROLLE: Wow. Look at this. CHRISTINE MCKINLEY: We
can't touch this, right? I'm being careful. Being careful. Touch with your eyes. BUDDY LEVY: That
handwriting's amazing. CHRISTINE MCKINLEY:
The minute she told me I couldn't touch the
book, all I wanted to do was touch that book. I wasn't even looking
at what was in it. So what's the significance
in learning so long after the Revolutionary
War who these people were? Well, I think it changes
our perception of history, where we thought that we just
had these lone agents that were spies going into enemy lines
and gathering information. Now we discover that there
was an intelligence system of people. SCOTT ROLLE: Well,
what's interesting, too, is when you look at it,
where we are today, especially in the intelligence community,
and you look back at this and see this may be where
it really all started. Possibly, yes. BRAD MELTZER: The Culper
Ring helped uncover the plot by America's greatest
traitor, Benedict Arnold, to betray his country. But what I want to know
is what happened to them? And is there a chance
they still exist today? Buddy, Mac, and Scott are
headed to the Culpers' base of operations on Long Island to
see if they can find out more. ROBERT SISLER: Washington had
determined after the Battle of New York he couldn't get
stuff through Westchester County because there were too
many British around there, so he came way out here. Nobody would ever suspect
that they were transferring information across
the sound from here, and that's the reason
they picked this area. This was a spot from which
they disseminated the messages. Not very populated
at the time? Five houses.
CHRISTINE MCKINLEY: Oh, wow. SCOTT ROLLE: Wow. FYI, this is one of them. The house behind you was
built by Phillips Roe in 1755. He became a member
of the spy ring, and his brother, Nathaniel Roe. And they were the ones picked
up and delivered the messages. Austin Roe used to ride in
once a week on his horse to New York City, pick up the
information that was gathered in the city, bring it
out here to Phillips Roe and his brother, Nathaniel Roe. What was their
relation to Austin Roe? They were cousins. Oh. BUDDY LEVY: OK. ROBERT SISLER: And
these gentlemen would deliver the information
to Caleb Brewster, who used to run across the sound
once a week in his whale boat. And they would always
come into a different cove and pick up the information,
and he would deliver it back to Connecticut. But it's a long
row-- it's 12 miles-- and the sound was laced
with British ships. So you had to be
stealthy and careful. BUDDY LEVY: Amazing. So we're talking about
riding on horseback from here in Setauket, 55 miles
to New York City, and returning here
with a message that Caleb Brewster would row
physically across the Long Island Sound to Connecticut to
deliver to Benjamin Tallmadge. ROBERT SISLER: That's right. CHRISTINE MCKINLEY: Yeah. Spying is not nearly
as athletic now. Incidentally, with
respect to whale boats, I think it might be of
interest to you people to see what one looked like. Just imagine that you're
Captain Brewster coming across the sound
in this, with maybe a dozen guys rowing,
six on each side. And the storms on the sound
can come up very quickly. And there's not much
free board on this boat. It must've been very dangerous. The British would have
seen them very easily. They'd have been sitting ducks. And I think the guys
were pretty, pretty brave to do this. Yeah, me too.
BUDDY LEVY: Tough. Tough.
Yeah, that's the word. Tough. These guys are amazing. They ride 110 miles round-trip
to gather the information, and then they row 24 miles
across Long Island Sound to deliver it. Forget the Iron Man Triathlon. This was true endurance. The thing I'm most
impressed by is that they're doing it with
the British everywhere, all around them. These guys know
if they're caught, they're going to
be shot on sight. So one thing they did was try
to have codes inside codes inside codes. Some of them were literally
hidden right in front of everyone's faces. ROBERT SISLER: This is a
typical North Shore cove where Caleb Brewster
would have come in to pick up his messages. Now you see what looks like
a clothesline over there? You see anything unusual
about this clothesline? - No.
- Nope. No. It's actually a coded message. What? Really? BUDDY LEVY: Come on. ROBERT SISLER: Yeah,
it's a coded message. You mean to tell
me that there's crucial information in here that
people of Setauket would know? Absolutely. Now, this was an Anna
Strong's clothesline. And Anna hung the
petticoats to help Culper Sr. in the early days,
and later the Roe brothers. What did the handkerchiefs
and the petticoat signify? The petticoat signifies that
Caleb Brewster had come in. And the number of handkerchiefs
told which of the many coves he came into. So Caleb Brewster's here,
and he's in the fourth cove. ROBERT SISLER: That's right.
He's in the fourth cove. They wouldn't have suspected
her at all, would they have? No, because she was
just a woman by herself. But she furthered the cause. CHRISTINE MCKINLEY: All the
while, just doing her laundry. ROBERT SISLER: Yeah. CHRISTINE MCKINLEY: Just
innocently doing the laundry. Nobody would suspect
her of anything. One of the little known
stories about the Culper Ring is that there were a great many
women who helped its cause. And think about it-- women had the
perfect cover story, because back then,
no one expected they'd be involved in something
that was so nefarious. Anna Strong and the other female
members of the Culper Ring led the way for some of the
most successful female spies of all time. Among the most
well-known was Mata Hari, who spied for the Germans
during World War I, and Julia Child, one of my
heroes, who, believe it or not, spied on the Nazis
during World War II. Now, one of the
most famous spy of all was one went under
the name of Agent 355. There are some historians
who think 355 was simply a number for a female. So the whole story
got a little twisted. So 355 may or may
not have existed. Depends upon which historian
you want to listen to. I studied them for two years,
and the Culper Ring still surprises me. These people were the
precursor of the CIA, the first civilian spy
agency in our history. They helped foil the plan by
Benedict Arnold that would have allowed the British
to win the war, and they're one of the first to
treat women as true spy equals. And one of the best
parts of the story? There's still major debate
about Agent 355's identity, or even if she was real. It seems like the trail's
gone cold with Agent 355, but the question remains. Did the ring die with her, or
is it still in existence today? The Culper Spy Ring, one of
the greatest secret creations of George Washington,
was lost to history for more than a
century and a half. It wasn't until the 1930s
that this crucial part of American history was
actually found again. BRAD MELTZER (ON
PHONE): Agent 711. Hey, Agent 711. That's Washington. BRAD MELTZER (ON PHONE): If
you're going to pick a guy, you've got to pick the top guy.
SCOTT ROLLE: Yeah. Absolutely. CHRISTINE MCKINLEY: We
think we cracked it. BRAD MELTZER (ON PHONE): Yeah.
Tell me what you got. Well, the Culper Ring
uncovered Benedict Arnold's nasty plot to hand
over West Point and helped us win the
American Revolution. We couldn't have
done it without them. BRAD MELTZER (ON PHONE):
Now you see my obsession with the Culper Ring, right?
- Yes. BRAD MELTZER (ON PHONE):
It is an unwritten moment of American history,
and Benjamin Tallmadge and his group
bring us to a point that we would have
otherwise not been at. CHRISTINE MCKINLEY: Absolutely.
BRAD MELTZER (ON PHONE): OK. You found that piece. What about Agent 355? SCOTT ROLLE: Well,
we're still not sure, Brad, because we're being
told by some that it was just a term, a spy term for lady. - We saw that in the code book.
- Exactly. And then we're also
hearing, though, that it was a specific woman
who had a lot to do with this. BRAD MELTZER (ON
PHONE): You know, there are people
out there who will say she's absolutely fake,
she's a myth, she's an amalgam. But there are people who insist
that 355 is a real person, that she actually saved us, that
she actually did stuff for us, and that no one
knows who she is. And I found a woman who
is convinced of that. Oh, cool. BRAD MELTZER (ON PHONE): She's
someone who has studied her for years, can tell
you exactly what she did for American history. I don't know if I believe her. And if she's right, I want
to know who this woman really is that we owe a great
deal of thanks to. I want her to be right. BRAD MELTZER (ON PHONE):
I want to-- listen, I wan her to be right, too. And I want to know about
her for my daughter. Yeah. BRAD MELTZER (ON PHONE): I want
my daughter to have that hero. ANDREA MEYER: So behind us
here is West Point, which was the American stronghold. And it would have kept
the British from moving up the Hudson River. West Point, as you
can see, kind of commands control of
the Hudson River here. It's really central to
any traffic up and down, and it really limits traffic
from going further north. If you were stopped
at West Point, you couldn't really continue. And during the
American Revolution, everyone recognized that
this was the thing that was keeping the British from
going further up the Hudson River. BRAD MELTZER: As we
know, Benedict Arnold was engaged in a plot to turn
over West Point to the British. All they had to do
was meet his price. His main contact on the British
side was a man named Major Andr , who, can we just
say, is either the best- or worst-dressed
ghost of all time? Some say the Culper Ring
had a spy in Andr 's camp. So when he travels to West
Point to negotiate with Arnold, the head of the Culper
spy ring, Major Tallmadge, knows that Andr 's coming. ANDREA MEYER: And
this was stopped by a spy known as Agent 355. And she was a female Culper spy. She was able to stop Benedict
Arnold by intercepting the correspondence in
Major Andr 's quarters. How did she get
the information? How did she get into
his quarters repeatedly? Well, we don't know exactly,
because good spies don't get caught. But we do know 355 was a female
member of the Culper Ring, and she was probably
Major Andr 's girlfriend. So she may have even been
sleeping with the enemy. Wow. What's the one rule of
every James Bond movie? You know it. Never trust a girl. The good thing for us? Andr had never seen James Bond. So what do we actually
know about Agent 355? We know just from her name
that she was both female and from the upper class,
because the word lady implied that somebody was
kind of an elite. You weren't the washer woman. You weren't just a woman. You were a lady,
somebody of breeding. Right. So we know that she was
probably well-connected because of that. We also know that she
probably was one of Major Andr 's girlfriends. He had a history
of always looking to marry up and make a name
for himself in the colonies. He was always looking
for advancement. There's a word for that. SCOTT ROLLE: You date up. He was looking to move up. He was definitely looking to
make his fortune and move up. CHRISTINE MCKINLEY:
The most amazing part of the story of Agent 355 to me
is that no one suspected her. You know, that you've got-- that
he might have had this woman in his office, in his life,
and telling her secrets, letting her overhear. But since he thought women
had no political opinions and no vested interest, would
just-- would not suspect her. I mean, to me, it speaks to the
power of being underestimated. And he probably didn't think
she was one bit interested in politics. Well, women were assumed to
have the same political views as their fathers
or spouses, so it would have been very easy
for a patriotic woman to be assumed to have the same
political views as her father. Andrea, we've heard that 355
was just a code word for lady, that it really wasn't a person. But obviously you
think otherwise. What proof do you have of that? Well, first of all there's a
letter that specifically refers to a lady working with the ring. That's August 15, 1779, and
Woodhull talks about the fact that she's going to start
working with the ring shortly. BUDDY LEVY: That's Culper Sr.
- That's Culper Sr., yes. There's a point in the
Culper correspondence where they suddenly are
reporting really, really good information. They go from not reporting
anything of use-- it's all old-- to suddenly, right
after 355 is mentioned, they're getting the innermost
secrets of the British army. They're reporting
practically black ops. They're reporting a
counterfeiting operation, things that only could have
come from British headquarters. So what information about
the plot did she discover? Well, she definitely
discovered that Arnold plan to betray West Point. There was a letter with
Arnold's name in the margin of Andr 's correspondence
in June of 1780. So that's months
of correspondence that are being intercepted. Wow. At the point that
Andr was intercepted, Andr had just met with Arnold. They had agreed that Arnold
was going to sell West Point. And Andr was going
back to New York. He's met by a group of
three seemingly random guys. They're highwaymen. They're militiamen. So these three guys stop him,
and they're looking to rob him. So he doesn't seem
to have any money. And they said, hey, he
doesn't have any money. Let's see if we can get
a prize off of this guy. Wow. So they decide to take him to
the local American commander, Commander Jameson. Unfortunately, he's
kind of big on protocol, and has no idea what's going
on with the Culper spies. So he sends word
to Benedict Arnold, because there's a pass
from Benedict Arnold. And he said, gee, what's
going on, Benedict Arnold? Fill me in. Tallmadge finds out
what's going on, though. He interrupts and
he says, no, no. We've got to send
word to Washington. So Jameson compromised. He sent one rider to
Washington who was on the move, and another rider to the
closer Benedict Arnold. The rider to Arnold left first,
so Arnold got word and escaped. BRAD MELTZER: So Benedict
Arnold literally escapes by the skin of his teeth,
destroying his friendship with George Washington. History reports it is
the only time anyone ever sees George Washington
break down and cry. This was a betrayal by
one of his best friends. And with Culper
Ring information, Tallmadge almost had him. But you know what Washington
does when it all calms down? He sends the Culper Ring
after Benedict Arnold. George Washington,
American badass. So when Benedict Arnold
flees to New York and goes over to
the British side, his first assignment is to round
up the members of the Culper Ring. This is one of the greatest
unseen fights in US history. But in the end, Arnold
never really figures out what to do with his
life, and he certainly can't catch the Culper Ring. So he goes back and forth
from England to Canada before eventually dying
miserable in London. But the biggest
question remains. Whatever happened
to the Culper Ring, and do they still
exist in some form? The Culper spy
ring was the first of its kind, one of the best. Conceived by General
George Washington, the all-civilian spy
organization played a key role in the forming of our country. The group was so
secretive, they didn't even know who each other were. In fact, Washington himself
didn't know all the members. And this allowed
the organization to stay hidden for 150 years. The first records of the
ring appeared in 1930, when a series of letters were
found detailing the group's operations. The letters match
unexplained correspondence from the estate of President
Washington himself. Through analysis and research,
the members of the initial ring were identified. But no matter what we
know of the Culper Ring, the role they played in
America's independence can't be overstated. As for Agent 355, some say that
Arnold caught this great spy, though I'm actually not
convinced she even existed. Either way, though,
the legend of Agent 355 becomes the story of an American
hero in the truest sense, someone who sacrifices
everything and then goes unnoticed for the
rest of history. BUDDY LEVY: So is it fair
to say that Agent 355, a lady in the Culper Ring-- Yes. --exposed Benedict Arnold's
plot and saved the Revolution? Yes, definitely. So whatever happened to 355? 355 was captured
by the British. She was probably imprisoned. So she was probably
questioned by the British. Because the Culper Ring
continued to operate, there's no reason to think
that she ever betrayed her fellow ring members. And she died-- you
think she died in prison? ANDREA MEYER: I think
she died in prison. Ugh. There's no reason to
believe she was released. - Ugh.
- She was really quite heroic. SCOTT ROLLE: What
a sad end, too. Yeah. That's a true American hero. Yeah, really. And she is
completely forgotten. SCOTT ROLLE: It sounds like
there is some pretty good evidence that Agent
355 actually did exist. It seems logical that somebody
who was a girlfriend, maybe, or had some inside information
would have had to have been responsible for this. BUDDY LEVY: It doesn't surprise
me at all that Agent 355 could have been a woman. I was really impressed that
the Culper Ring was that sophisticated to use whatever
means necessary to get the information that
George Washington needed. CHRISTINE MCKINLEY: I
think in the context of the American Revolution,
anything that needed to be done should be done. I mean, if she was
sleeping with the enemy, and that's what it took,
if that won our Revolution, I'm grateful. BUDDY LEVY: This has been great. I mean, we're standing here on
the banks of the Hudson River right across from West Point,
where Benedict Arnold nearly sold out America. And it's the kind of history
that I love most because you say to yourself, I had no idea. And how-- and how
did we have no idea? How did we not learn
about this in school? The Culper spy
ring was absolutely crucial to beating the British. And that's exactly the point. It's not just, did they exist? We know they exist now. But it really seems to
come down to this group and what they were able
to accomplish that did it. They weren't these highly
trained operatives who we think of when we think of spies. These were ordinary
American people who happen to believe
so much in the cause that they're willing to
put their lives on the line and be part of
this big, big ring. And think of just
how committed they were to that because they had
already seen their predecessor, Nathan Hale, hanged. CHRISTINE MCKINLEY: Yep.
SCOTT ROLLE: They knew that-- CHRISTINE MCKINLEY:
Knew the risk. SCOTT ROLLE: --and
they did it anyway. CHRISTINE MCKINLEY:
That's right. SCOTT ROLLE: It's unbelievable. BUDDY LEVY: And the cool
thing about this story is that the Culper spy ring,
about whom we knew virtually nothing, are responsible for
bringing down Benedict Arnold and changing the course
of American history. CHRISTINE MCKINLEY: And
Agent 355, who we still don't know much about, might
have been the one feeding the Culper spy ring the
information they needed to do that. Who else would have had access
to that type of information but a girlfriend of a major? CHRISTINE MCKINLEY: And not
been suspected for that long, because women just weren't
seen as political beings. They wouldn't have thought
that they had anything invested in the Revolution,
which is crazy. The pieces of the puzzle fit. I think she existed. I just don't-- not
sure who she was. And who would've guessed
the spymaster was George Washington? I mean, of all people, we never
thought that kind of thing about him. CHRISTINE MCKINLEY: It's the
ultimate brains over brawn. I mean, the British were
stronger, they were bigger, and America was outgunned. But they outfought them,
and I love that part of it. For the first
time in our history, we had an organized spy ring. And really, this is, in my mind,
what led to the CIA, the FBI, and everything we have today.
CHRISTINE MCKINLEY: Yeah. It's the birth. Makes me kind of wonder
whether there are embedded regular folks still today
who are doing that work. SCOTT ROLLE: I'd almost
say for sure, wouldn't you? Oh, absolutely. Absolutely. The skies have opened. We better get out of
here and tell Brad. All right. Before we get drenched,
let's go talk to him. BRAD MELTZER: The trail
of the Culper Ring dies out following
the Revolution. And it seems that they cease to
operate around 1785, at least as far as we know. But let me tell you the
greatest secret of all. I think it's still around. A few years ago, I got a call
from the Department of Homeland Security, asking me to come
brainstorm different ways that terrorists can
attack the United States. They read my novels. They saw my research. And I was honored to be part of
what they called the Red Cell team. I kept the secret until
they asked me to go public. But the point is, I was a
regular civilian brought in to help our country, just
like the Culper Ring. Even better, last week,
when I was telling a former top national security
agent about the Culper Ring, the phone went silent. And he said to me,
you know, there are rumors they're still here. But the best legacy
of the Culper Ring is that it supports
my core belief. You see, I believe ordinary
people change the world. I don't care where
you went to school. I don't care how
much money you make. I believe that regular
people, like the Culper Ring, is how the world gets changed. Don't ever forget, history
is a selection process. Most of us think that it
chooses a moment and a person and it puts them together. But history chooses each
of us every single day. And the only question is,
will you hear the call?
