America’s First Fighting Captain: Jeremiah O’Brien

Once upon a time, right after the Battle of Lexington and Concord (and the somewhat dubiously naval Battle of Chelsea Creek), the tiny village of Machias, Maine (then part of the Colony of Massachusetts) decided to revolt against the United Kingdom. The question was largely theoretical, as you’d expect of a village of only twenty houses. But then, the very foolish young British Navy captain of the HMS Margaretta (escorting the merchant ships Polly and Unity on their errand to get wood for the British Army to build barracks) threatened to turn his six-pounder cannon against the town unless they took down their newly erected Liberty Tree.

The local militia took the threat seriously, and formed a desperate plan to capture the captain and his officers when they attended church on Sunday. This plan was foiled inadvertently (by a bored guy looking out the window, seeing men with muskets, and promptly jumping out the window and running into the woods), and the officers fled back to the Margaretta. Captain James Moore weighed anchor, abandoning the merchant ships he was escorting, and tried to escape downriver, while being fired upon by practically every man in town, while they followed in canoes and rowboats as well as along the shore on foot and horse.

On Monday morning, Dennis Wheaton was bored after their exciting Sunday. He started chatting to his buddy, John O’Brien, about how it would be easy to seize one of the merchant ships, and then use it to chase and capture the Margaretta. After all, she hadn’t sailed any farther than an island in the nearby bay. Two other friends came up, and got the idea floated to them. At which point, these four country lads went down the dock and captured the Unity.

This caused a little ruckus, and many of the townsfolk gathered around. The young men explained what they had done, and their brilliant plan. John managed to convince his eldest brother, Jeremiah (who was one of the militia leaders) to get with the plan. The crew of the Polly was a little more awake and not in the mood to have their ship captured, but one of the other militia leaders headed to East Machias with some men to capture another merchant ship. They would manage the capture all right, but then run their ship aground and have to send a rowboat to warn the Unity that they couldn’t help out.

In the end, 34 men boarded the Unity. The youngest O’Brien brother, Joseph, was only sixteen, and his elder brothers forbade him to go. He snuck aboard anyway, as the 35th man. (The brothers also had to dissuade their old dad from coming along.) The village crew included Wheaton, the other five O’Brien brothers, and Jeremiah’s free black servant Dick Earl.

Once they were close to the bay, the villagers decided to hold an election for captain. Jeremiah O’Brien was elected unanimously. He immediately offered the chance for anyone to leave before battle, and three men took him up on it. They were down to 31 men. (32 including Joseph down below.)

They planned their attack. They would catch up, then board and storm the English Navy’s little warship. They had some muskets and fowling pieces, a little naval wall piece, a few swords, and a lot of pitchforks. They also had the advantage of having several excellent marksmen among their fighters.

But the Margaretta had forty men, with muskets and cutlasses for every man. And those six pounders. And several wall pieces. It was ridiculous for these American rebels to think that they could win, much less go around yelling, “Surrender in the name of America!” The first two Americans to man the wall piece were blown away by one of the cannon. The next American to try his hand at the wall piece blew off the Navy helmsman’s head. The Navy sailors scattered, which gave the Americans room to board. Pitchforks proved to be a pretty nasty boarding weapon, and the Americans took weapons away from the Navy men who dropped them. The Navy captain took notice of his opposite number directing the battle, and started throwing hand grenades at Jeremiah O’Brien. Jeremiah had two buddies acting as his wingmen, though, and they both deliberately aimed their muskets at the Navy captain, wounding him fatally in the chest. That was pretty much the end of the battle.

So in point of fact, the men of Machias did beat the British lion. They captured the Margaretta and hid her upstream, landed on a beach and camouflaged with tree trunks. Then they turned the Unity into an official naval vessel of the Machias Committee of Safety and then of the Massachusetts Navy, under her new name of the Machias Liberty. Despite inadequate funding from Boston, they managed to make life difficult for the British in their patrol area and all the way to the Bay of Fundy. Other ships captured by O’Brien included the Diligent and the Tapnaquish. After a lot of political maneuvering, Massachusetts let O’Brien go, and he became first a Ranger captain on the land, and then a privateer captain, commanding the Resolution, the Cyrus, the Tiger, the Saint Vincent, and the Hannibal, all privately owned. His brother John also became a privateer captain, wreaking all sorts of havoc.

Eventually Jeremiah O’Brien was captured, first imprisoned in Brooklyn and then in Plymouth, England. He escaped to France along with other American prisoners and returned home. He became a Selectman and a customs collector, remaining a civilian homebody during the War of 1812.

But in 1814, the British came back to Machias Bay, taking the small American fort at Machiasport and moving upriver on barges to take Machias. O’Brien put on his Revolutionary War uniform, mounted his one-eyed white horse, rode at breakneck speed to the village, and tried to rally the villagers to resist. But the men of Machias were not what they had been, the British Army forces were pretty darned numerous, and he couldn’t persuade anyone to follow him. (To be fair, he was 70 years old, which was a lot older then.) He retired cursing in spectacular fashion.

The British occupied the village without destroying anything. When they searched the houses, the villagers made sure there were no arms for them to find. (Because all the guns were hidden out in the woods.) Captain O’Brien ended up offering cider and cake to the men who searched his house. The British officer asked their host to give them a toast.

Captain Jeremiah leapt up. “Here’s to the success of the American arms!”

There was a moment of awkward silence. Then the British laughed, and their officer counter-toasted, “Here’s to the health of the King!”

Captain Jeremiah O’Brien died in 1818. His family were Protestant Irish from Dublin: dissenters in Ireland, Baptists by conviction, and members of the Congregational Church in Machias. His son, also named Jeremiah, would become a Congressman for Maine. His descendants and relatives are still many.

You can read all about it in The Life of Captain Jeremiah O’Brien of Machias, Maine, by the Rev. Andrew M. Sherman.


Filed under History

2 responses to “America’s First Fighting Captain: Jeremiah O’Brien

  1. Sounds like a corker! Blood of yours?

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