Jeremiah O'Brien led Maine backwoodsmen to capture the British ship Margaretta in 1775.

From the early days of the Revolution, when ships still rode low on the horizon and the forests reeked of pine and gunpowder, a single raid can feel like a spark that lights a larger flame. This is the kind of moment that turns a quiz question into a doorway for bigger ideas—about courage, leadership, and the stubborn smoke of resistance that rose from the Maine shoreline. So let’s step into that story, the story of Jeremiah O’Brien and the capture of a British ship, and see what it can teach modern cadets and curious readers alike.

Who led the Maine backwoodsmen?

Picture a ragtag group of forest-dwelling colonists, the kind of folks who know the lay of every trail and the sound of the tide. It’s 1775, and the colonial cause needs a win that feels personal as well as strategic. The question that often comes up in a history chat or a school quiz goes like this: who led those Maine backwoodsmen in seizing the British ship Margaretta? The options you might see are:

• A. Benedict Arnold

• B. Jeremiah O'Brien

• C. George Washington

• D. John Paul Jones

The correct answer is B, Jeremiah O'Brien. He wasn’t a high-ranking general in a grand hall; he was a leader who understood the grit of the coast and the resolve of local communities. O’Brien’s reputation rests on the idea that a small, determined band can alter the course of a campaign. It’s a reminder that battlefield innovation isn’t only about the biggest ships or the loudest cannon. It’s about individuals who are willing to risk what they have, right where they live.

What happened on the Margaretta, and why did it matter?

The Margaretta raid reads like a compact epic: a ship taken not by fleets in a grand harbor but by a freshly organized crew that knew the local seas as well as their own palms. The ship—British, armed, and semi-obsolete—became a target because the colonists were hungry for momentum. They didn’t wait for a formal announcement or a letter from far-off capital. They moved at dawn, loaded a small boat, and navigated a coastline where fog and soundings could hide a ship as easily as a friend.

This was one of the early naval engagements of the American Revolutionary War, a note that compels us to rethink what “naval power” can look like in the early, improvisatory days of American resistance. It wasn’t a grand battle with a big fleet; it was a daring action that showed how a collective effort—rooted in place and community—could challenge distant authority. The capture of Margaretta sent a clear signal: the colonists would fight at sea as well as on land, and they would do so with local knowledge guiding their timing and tactics.

Why this matters for leadership and teamwork

If you’re part of an NJROTC-related circle—or any group that studies history with an eye toward real-world values—you probably recognize a familiar thread here: leadership isn’t only about charisma or rank. It’s about making a plan with the resources at hand, building trust among teammates, and executing with calm under pressure. Jeremiah O’Brien didn’t command a large squad; he commanded confidence. He was able to marshal fellow backwoodsmen, coordinate a risky operation, and make a strike that would echo in naval memory for years.

This is the kind of lesson that sits nicely next to the dry, technical stuff commanders train for: seamanship, navigation, and the mechanics of small-unit operations. The Margaretta raid highlights several practical leadership qualities:

• Local knowledge as force multiplier: understanding terrain, winds, and tidal patterns can turn a modest force into something formidable.

• Small-unit initiative: decisive action by a tight group can set a tone for a wider movement.

• Moral clarity and resilience: the willingness to risk danger for a cause helps sustain a team through tough moments.

• Clear communication under pressure: quick, quiet coordination can mean the difference between success and loss.

A broader echo through time

We tend to think of famous naval figures as towering, almost mythic, individuals. John Paul Jones, George Washington, Benedict Arnold—the names often fill the marquee. But the Machias episode where O’Brien led the backwoodsmen reminds us that maritime history also lives in the margins: in quiet coves, in the kind of raids your grandparents might have told you about around a campfire. It’s a reminder that the war’s early days were not one long, smooth ascent but a series of sharp, improvisational moves by people who believed their small town mattered.

The story also offers a useful contrast. Jones, Washington, and Arnold each embody different facets of leadership—strategic planning, overarching command, or a controversial, high-stakes daring. The Maine raid sits closer to the ground level: a proof that leadership can emerge anywhere, and that maritime resistance isn’t just the purview of the big ships and famous captains. It’s pragmatism, courage, and a willingness to act with the hand you’re dealt.

Connecting to the modern reader: what can students take away?

For students who study history with an eye on public service, maritime heritage, or leadership, the Margaretta raid isn’t just a footnote. It’s a case study in small-team effectiveness and situational improvisation. It invites a few practical takeaways:

• Resourcefulness beats sheer might when the odds are against you. The backwoods crew had limited tools but a fierce will. In any team setting, that same logic applies: optimize what you have, don’t complain about what you lack.

• Local engagement matters. When communities see themselves as stakeholders in a larger story, they mobilize. The sense of shared purpose fuels momentum that no decree can manufacture from afar.

• Courage compounds. The more people see risk taken by peers, the more likely they are to step up themselves. That ripple effect matters in classrooms, labs, and field missions alike.

• History rewards curiosity. The Margaretta raid isn’t only about a ship captured; it’s about the questions it raises: How did they plan it? What obstacles did they overcome? How did the men coordinate under pressure?

A quick historical snapshot, side-by-side with other leaders

Let’s not pretend the Revolutionary era was clean or simple. It wasn’t. But it’s helpful to sketch a quick contrast that makes the Maine raid feel more alive:

• Benedict Arnold: a figure whose career invites debate about loyalty, risk, and ambition. He’s a reminder that leadership can falter when motives become muddled, even as skills stay sharp.

• George Washington: the big-picture strategist who learned to translate sweeping goals into practical campaigns. He shows how patient planning can align many moving parts.

• John Paul Jones: the fearless sea captain whose daring exploits became a symbol of American naval stubbornness and ingenuity.

The Margaretta raid sits in the middle ground, a vivid example of how a community can act decisively when a moment calls for it. It’s not a grand battlefield portrait, but a crisp, real moment when people in a tight-knit region chose to stand up and steer history with their own hands.

A few questions to carry forward

If you’ve read this far, you’ve probably started to wonder: what would I do if I stood on a wharf with a plan and a handful of companions? Could a small team, working with what’s at hand, shift the balance in a tense moment?

Here are a couple of prompts to chew on—without needing a textbook or a lecture hall to feel the weight:

• How does local knowledge shape strategy when you’re outnumbered?

• What does leadership look like when you can’t call for reinforcements or fancy equipment?

• In your own teams, how do you build trust quickly enough to execute a risky plan?

A few closing threads

The Maine backwoodsmen and the Margaretta remind us that history isn’t just about dates and names. It’s about people who take action when the moment arrives. It’s about weathering uncertainty with a plan and a crew that believes in one another. It’s about seeing how a small victory—earned with grit and quick thinking—can push a larger story forward.

If you ever read a trivia card that asks who led the Maine backwoodsmen, you’ll now have more than a name to offer. You’ll have a compact narrative about leadership under pressure, about how a coastal community could improvise, and about how a single raid in 1775 helped widen the gulf between a distant empire and the people who lived along its shoreline.

And that, in the end, is the kind of history that feels alive—that makes a classroom story feel like a voyage. Jeremiah O’Brien didn’t just lead a raid; he helped stitch a thread into the broader fabric of American maritime resistance. The Margaretta’s capture is a small event with a loud echo—a reminder that courage often shows up in the most modest packages, ready to inspire the next generation of sailors, scholars, and dreamers.