Travel in Time with Dan | Black Rock Harbor, Long Island Sound, Connecticut — the American Revolutionary War
⚠️ Author’s Note: The following is a fictional historical interview. Caleb Brewster (1747–1827) was a real American naval officer, privateer, and intelligence operative who played a significant role in both the Whaleboat Wars and George Washington’s Culper Spy Ring during the American Revolutionary War. Operating out of Black Rock Harbor in what is now Bridgeport, Connecticut… the third-largest privateering port in Connecticut behind New London and New Haven… Brewster commanded whaleboats on the Long Island Sound, which served as a dangerous no-man’s land between Patriot-held Connecticut and British-occupied New York and Long Island. The Sound’s geography was strategically critical: deep enough for American boats to operate freely, shallow enough in its rivers and creeks to allow escape from larger British vessels that could not follow. Privateers like Brewster operated under Letters of Marque… legal authorizations issued by the American government, which issued approximately 1,700 of them during the Revolutionary War… that permitted private citizens to raid British supply lines and share captured prizes with the government. Britain considered them pirates, punishable by death if captured. Simultaneously, Brewster served as a primary courier and field operative for the Culper Spy Ring, Washington’s first organized intelligence network, passing intelligence across the Sound between Long Island agents and the Continental Army. Black Rock Harbor was protected by Fayweather Island, Fort Union, and the Black Rock Battery. The United States never signed the 1856 Treaty of Paris outlawing privateering, meaning the practice remains technically legal under the U.S. Constitution to this day. This imagined interview takes place on the Long Island Sound during an active raid. The historical facts are real. The dialogue is creative fiction, inspired by Brewster’s documented toughness, his dual role as fighter and spy, and the remarkable resourcefulness of the privateer enterprise.
📍 Setting: A whaleboat on the Long Island Sound — sometime during the American Revolutionary War, night. The boat is moving with the particular quiet urgency of people who are very good at what they are doing and very aware of the consequences of doing it poorly. The Sound is dark. The Connecticut shore is behind us, the British-occupied Long Island shore uncomfortably close ahead. There are six men at the oars, moving with the practiced silence of people who have done this before and intend to do it again. At the stern, a broad-shouldered man in his thirties with a weathered face and the easy authority of someone who commands not by volume but by competence is watching the Long Island shore with the focused attention of a man reading something most people cannot see. He does not look like a spy. He looks exactly like what he also is: a fighter who has learned to be useful in more than one way. He glances over as I settle into the bow, evaluates me in the practiced way of a man who evaluates everything he encounters, and then returns his eyes to the shore before he speaks.
Brewster: (Quietly, without turning)
Keep your voice down and your head below the gunwale when I tell you to. Other than that, ask what you want. Long nights out here. I’ve found talking helps as long as you do it at the right volume.
Dan: (Quietly) What are we doing out here tonight?
Brewster: Two things, same as most nights. (A glance at the Long Island shore) There’s a British supply vessel anchored in that cove about a mile east of here. She came in this afternoon carrying provisions for the garrison at Oyster Bay — salt meat, powder, some coin. We’re going to relieve her of the powder and the coin and whatever else seems worth taking, and then we’re going to be back on the Connecticut side before anyone on that garrison figures out what happened.
(A pause)
That’s the first thing.
Dan: And the second?
Brewster: (With the careful economy of a man who discusses the second thing with considerably fewer people than the first)
There’s a man on Long Island who has information that General Washington needs. My job is to pick it up and get it across the Sound to where it can travel north to headquarters. The raid is cover. If the British see a whaleboat on the Sound tonight, they see a privateer raid. They don’t see a courier run. That is the point.
Dan: You’re doing both simultaneously. Privateer and spy on the same boat on the same night.
Brewster: (Dryly, still watching the shore)
The general is a practical man. He doesn’t like waste. Neither do I.
Dan: Let’s back up. The Letter of Marque… explain what that actually means for you and these men.
Brewster: (Settling back slightly, the shore still in his peripheral vision)
It means the difference between a privateer and a pirate is a piece of paper, and I have the paper. (A slight pause) What it says, in the language the government uses for these things, is that I am legally authorized by the United States of America to conduct offensive operations against British vessels and supply lines using my own boat and my own men. Whatever I take, I keep a share. The government takes a share. The men take a share. Everybody who took the risk gets something from the risk.
Dan: The British don’t see it that way.
Brewster: (Flatly) No. The British see a man with a Letter of Marque the same way they see a man without one. They call us pirates. If they catch us, they hang us. The paper does not save you from a British rope. It only saves you from an American court. I try to keep that distinction clear in my mind when I’m making decisions about how close to go.
Dan: How close do you go?
Brewster: (The ghost of something that might be a grin in the darkness)
Close enough to be useful. That’s the honest answer. There is a calculation every time… what the intelligence or the prize is worth against what the risk of obtaining it costs. I have men in this boat who have families on the Connecticut shore. I do not make that calculation lightly.
(More seriously)
But I also know what happens if the British keep their supply lines intact and Washington doesn’t get the intelligence he needs. I know what that costs too. The calculation always has two sides.
Dan: Talk to me about the Sound itself. You know this water.
Brewster: (With the particular warmth of a man talking about something he genuinely understands)
Better than most men alive, I’d say without too much vanity. The Sound is not one thing. It’s a hundred things depending on the tide, the wind, the season, and the time of night. There are places in this water where a British man-of-war draws too much to follow us, where we can duck into a creek mouth and simply disappear while they’re still trying to figure out which direction we went. That geography is worth more to us than ten cannons. We are smaller and faster and we know the water. They are larger and slower and they don’t.
(Quietly)
Black Rock Harbor specifically… the depth of it, the approaches, the way Fayweather Island sits… I could run that harbor blind in a storm. The British could not run it safely in daylight with good charts. That asymmetry is everything. You don’t beat a larger force by matching it. You beat it by finding the ground where size becomes a disadvantage instead of an advantage.
Dan: That’s the whole privateer strategy in one thought.
Brewster: That’s the whole war strategy in one thought, if Washington’s doing it right. Which he is, mostly. (A beat) We were never going to beat the British Navy head to head. We don’t have the ships. We don’t have the guns. We don’t have the trained sailors in the numbers they have. What we have is 1,700 Letters of Marque and a lot of men who know their local waters and are angry enough to get in a small boat at night and do something about it. You outsource the problem to the people best positioned to solve it, and you give them enough of a stake in the outcome to keep them motivated.
Dan: Patriotism and profit.
Brewster: (Simply) Patriotism keeps you out here when the profit doesn’t seem worth it. Profit keeps you out here when the patriotism gets tired. You need both. A man who tells you it’s only about one of those things has not spent enough nights on this Sound.
Dan: The spy ring… how does that work alongside the privateer operation? Washington’s first organized intelligence network, running right through this boat.
Brewster: (A careful pause, the shore very close now, his voice dropping further)
Carefully. That is the primary answer. Very carefully.
(After a moment, satisfied with the shore)
What I can tell you is that the Sound is not just a military obstacle. It is an information barrier. Long Island is occupied. The people on it who are loyal to the cause cannot walk into Washington’s headquarters and tell him what they know. The information has to cross the water. That crossing is what I do. I know the crossings. I know when to make them and when not to. And I know how to look, to anyone watching, like something other than what I am.
(Glancing at me)
The privateer raids are real. We genuinely take the prizes and disrupt the supply lines. That is not cover… that is the work. But it also means that a whaleboat on the Sound at night is not suspicious in itself. The British expect to see us. They expect to chase us. They do not expect that the man they are chasing is also carrying a message that will reach George Washington within the week.
Dan: What happens if you’re caught?
Brewster: (Without drama, which somehow makes it more serious)
If they catch me raiding, they hang me as a pirate. If they catch me carrying intelligence… (a pause)… they hang me considerably more deliberately. The British do not treat spies the way they treated Burgoyne’s men at Saratoga. There is no Convention. There are no honors. There is a rope and a short drop and that is the end of it.
(Looking at me with the directness of a man stating a fact)
I know that. Every man in this boat knows that. We go out anyway because the alternative is to leave the work undone, and the work is too important to leave undone. That is the whole of it. There is no more complicated answer than that.
Dan: Leaders find a way when resources are limited. That’s what this whole operation is.
Brewster: (Nodding slowly, the Long Island shore now very close)
We have no navy. No real one… not one that could stand against what the British put on this water. So we found another way. Small boats. Men who knew the water. Legal authorization that turned private courage into public service. The government said: we cannot do this ourselves, but we can make it possible for you to do it for us, and we will make it worth your while. And the men said yes. And it worked.
(Quietly)
That is not a complicated idea. It is just a correct one. When you do not have what the problem requires, you find what you do have and you ask whether it can be made to serve the same purpose. Usually it can, if you are willing to be creative about how you use it.
(A hand gesture… low, urgent… that stops the conversation instantly. The men at the oars slow. Everyone in the boat goes still with the practiced simultaneity of people who have rehearsed this without rehearsing it. The British supply vessel is visible now in the cove ahead, a darker shape against the dark water, a single lantern at her stern. Brewster studies it for a long moment with the complete attention of a man for whom this is the only thing in the world right now.)
(Without looking back, barely audible)
We’ll finish this conversation on the way home. Right now I need you to be very quiet and very still and trust that I know what I’m doing.
I was very quiet. I was very still.
The supply vessel was lighter when we left the cove than when we found it. The message from Long Island was in Brewster’s coat. The Connecticut shore emerged from the darkness ahead with the particular relief of a shore you were not certain you would see again.
Caleb Brewster made that crossing… in both directions, carrying prizes and intelligence simultaneously… more times than the historical record fully captures. He survived the war. He lived to eighty years old, which given the number of British ropes that had his name on them is either extraordinary luck or extraordinary competence, and probably both.
The Culper Spy Ring he served helped Washington win a war that could not have been won without good intelligence. The whaleboat operations he commanded disrupted British supply lines at a time when the Continental Army could not afford to feed a conventional navy. He did both from a small boat on a dangerous Sound, at night, under a letter of marque that the British would not have honored for a second.
Black Rock Harbor is still there. The Long Island Sound is still there. The geography that made the whole operation possible… the shallow creeks, the deep harbor, the water that knew Brewster better than the British ever would… is still there.
The leadership lesson is the one Brewster named between shore and cove on a dark night in the middle of a war: leaders find a way when resources are limited. Not a perfect way. Not a safe way. A way that uses what exists… the small boats, the local knowledge, the motivated men, the geography… and asks whether it can be made to serve the purpose that the resources you don’t have would otherwise serve.
Usually it can.
1,700 Letters of Marque. A no-man’s land full of whaleboats. A spy ring running messages under cover of raids that were also genuinely raids.
The United States never signed the 1856 treaty outlawing privateering. Technically, legally, constitutionally, it could still happen. The letter of marque is still in the Constitution, waiting.
Caleb Brewster would probably find that satisfying. ⚓🌊
Travel in Time with Dan is where travel, history, and leadership come together. Uncovering History. Inspiring Leadership.
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