Ahoy, mateys! Bootstrap Ginny at the helm, and my crew and I have been feelin’ the pull of a new tide — a rebel tide. With the 250th anniversary of these United States upon us, it’s high time we honor the salty dogs who took to the seas not for kings, nor crowns, nor gilded thrones… but for freedom, and for the rights of ordinary folk to chart their own course.

Aye, these weren’t your typical pyrates — though they had the same fire in their bellies and the same salt in their blood. These were privateers, men who sailed under a newborn flag, striking blows against an empire and helping forge a nation from the deck of a ship.

So between now and July 4th, every Friday’s Plunder will be devoted to:

THE REBEL TIDE

Privateers of the American Revolution

So grab your grog, pack your pipe, and settle in close to the lantern.

Jeremiah O’Brien

Today we sail north, to the cold, pine‑shadowed waters of Maine, where rebellion didn’t wait for declarations or signatures. It rose from the docks, from the timber yards, from the rough hands of men who knew the sea better than any king.

And at the heart of that first spark stood Jeremiah O’Brien.

Before the Continental Navy had a name… before Congress found its courage… before the Revolution even realized it was a revolution… O’Brien and his brothers seized their moment.

It was June 1775 in the little settlement of Machias. A British cutter, the Margaretta, had come to enforce loyalty with powder and threat. The townsfolk refused. The crown answered with violence. And the O’Brien brothers — Jeremiah, Gideon, John, William, Dennis, and Joseph — answered with something fiercer.

They gathered a crew of lumbermen, fishermen, and farmers. No uniforms. No training. No cannons. Just grit, muskets, axes, and the kind of courage that comes from having nothing left to lose.

They boarded the sloop Unity, raised a makeshift flag, and rowed straight into history.

The battle was brutal and close — grappling hooks, musket fire, hand‑to‑hand fighting on slick decks. But when the smoke cleared, the impossible had happened:

Jeremiah O’Brien had captured the first British warship of the American Revolution.

No navy. No commission. No permission. Just defiance, saltwater, and the raw will of a people who refused to bow.

O’Brien didn’t stop there. He went on to command additional vessels, harass British shipping, and defend the Maine coast with the same stubborn fire that lit his first victory. But it’s that moment aboard the Margaretta — that wild, desperate, glorious moment — that echoes across the centuries.

Because it wasn’t just a battle. It was a declaration.

A promise whispered across the waves:

“We will not kneel.”

Jeremiah O’Brien was the spark before the blaze, the rebel before the rebellion, the man who proved that freedom sometimes begins with a single, furious leap across a ship’s rail.

And so the Rebel Tide rises.

Historical insights for this Plunder were inspired by Eric Jay Dolin’s excellent book Rebels at Sea. Highly recommended for fellow lovers of maritime history.

Til next time, Fair Winds!

To the ghosts that guide us, the storms that test us, and the gold that waits for those who dare — may our ink never run dry and our courage never fade. Raise your tankards, mates… for the sea still remembers our names.