It was late in September or early in October, 1776, that the “Margaretta,” re-named the “Machias Cruiser,” sailed from Machias, going westward. When in the vicinity of Mt. Desert, O’Brien espied in the offing what he supposed was a British merchant vessel, going to the eastward. Upon drawing nearer to the vessel, with a view to giving her battle, O’Brien ascertained that she was a British warship. Crowding on all sail, he turned the prow of the “Machias Cruiser” away from the enemy, for which he well knew his vessel was no match. He hoped to be able to reach Machias Bay, and there find harbor and shelter. The British warship was gaining rapidly on the American vessel; sending a shot now and then after O’Brien, whose vessel, however, remained unharmed. When off Sawyer’s Cove, about forty miles to the eastward of Mt. Desert, O’Brien, who saw that he would be overtaken by his fleet pursuer, ran his vessel into the cove, beached her on the flats, and he and his men jumped into the shallow water and swam and waded ashore. They found shelter in half a dozen dwelling houses in the vicinity. This was the first and the last defeat Captain John O’Brien, in his long career, ever suffered.
As near as can now be ascertained, it was sometime during 1778 or early in 1779, that Captain John O’Brien removed to Newburyport, Massachusetts; and his brothers, Dennis and Joseph, soon after followed him to the same village in Newbury township. In Newburyport, the three brothers jointly engaged in mercantile and commercial pursuits.
On the 21st of September, 1779, Captain John O’Brien and Miss Hannah Tappan, daughter of Richard Tappan, were united in marriage. They had first met during a previous visit of Captain O’Brien to Newburyport. It is said that Miss Tappan was at first attracted to Captain O’Brien because of what she had heard of his highly meritorious connection with the capture of the “Margaretta”; in her eyes he was, therefore, a hero.
In Newburyport, Captain and Mrs. O’Brien moved in the best society of the place; his reputation as a prominent character in connection with the Revolution, and his upright, manly bearing, opening to him the avenues of entrance to society. As a full-dressed gentleman of the period, he is said to have made a very fine appearance. One of Captain John O’Brien’s descendants, a grandson, thus speaks of his ancestor: “In the olden times, when my grandfather was in his prime, his ships visited the Indies, and the rich owners lived in stately mansions and made a great display of style in dress and manner. The gentlemen of fashion almost outdid the ladies in the neatness of their attire. I have in my possession some articles of dress worn by my grandfather when he lived in Newbury; they answer to the description given by the historians of the time of the brilliant appearance which a full-dressed gentleman must have made in a social party. A long blue coat, with ample pockets and silver buttons; a white satin vest, of capacious dimensions; velvet breeches reaching to the knees and fastened there by silver buckles; silk stockings and buckled shoes; ruffles in the bosom, and at the wrists, and a richly embroidered scarf around the neck—all this gorgeous array presents a striking contrast to the studied simplicity of a gentleman’s dress in our day. Later in life, my grandfather laid off some of this finery; but he retained his ‘small clothes’ and knee buckles and silk stockings to the last.
During the summer of 1780, Captain John O’Brien and his brother Joseph built in Newburyport a vessel intended for the privateer service. She was named the “Hannibal,” and was to carry twenty-four guns and have a crew of one hundred and thirty men. On her first cruise, to Port au Prince, San Domingo, she was commanded by Captain John O’Brien; he captured several important British prizes.
After the capture of the “Hannibal,” while in command of Captain Jeremiah O’Brien, by the British,[[26]] late in 1780 or early in 1781, Captain John O’Brien and a few others built in Newburyport another vessel for the privateer service, which was named the “Hibernia.” She was a small vessel, but a splendid sailer. The “Hibernia” carried six three-pound guns. Of this vessel Captain John O’Brien took command (Captain Jeremiah O’Brien was then on board the prison ship Jersey, at Wallabout Bay). Captain John O’Brien inflicted great damage upon British shipping with the “Hibernia.” On his first cruise, which lasted less than four weeks, he captured three brigs, a ship and two schooners from the enemy. During this cruise O’Brien met with a sixteen-gun British ship of war, with which he engaged in a fight lasting nearly two hours. From this evidently unequal encounter he escaped with the loss of three killed and several wounded. One of the wounded men on board the “Hibernia” had an arm shattered by a cannon-shot from the enemy. The surgeon on board, instead of proceeding to amputate the arm, stood trembling, afraid to undertake the operation. The wounded man was rapidly bleeding to death. Captain O’Brien drew his pistol, and, pointing it at the surgeon, said: “Do your duty, sir, or I’ll blow your brains out!” The arm was speedily amputated, and the man’s life was thereby saved.
As a result of a subsequent cruise in the “Hibernia,” Captain John O’Brien brought into Newburyport eleven British merchant vessels, all richly laden, out of a fleet of twelve with which he had fallen in off the mouth of the Narrows, below New York.
Captain O’Brien, while cruising in the vicinity of New York, espied a large vessel which he supposed was a British merchantman, and he at once “bore down” upon the craft. Upon ascertaining that the vessel was a British man-of-war, O’Brien immediately crowded on all sail, and, suddenly altering the course of the “Hibernia,” ran from the enemy’s vessel. The British man-of-war pursued the “Hibernia,” and as the former was the faster sailer, she was rapidly gaining on the American privateer. It was then nearly dusk. As soon as darkness settled down upon the water, O’Brien ballasted a hogshead, set firmly in one side of it a pole, at the top of which he placed a large, lighted lantern. Lowering the hogshead into the water, O’Brien ordered an anchor cast; the fog, by this time being so dense that the “Hibernia” could not be discerned by the British man-of-war. The heavy muffled sound of booming cannon was soon heard on board the American privateer. It proved to be the enemy furiously bombarding the floating hogshead, which had been taken by the British commander for the “Hibernia.” At length silence reigned. When morning broke, the British man-of-war was nowhere to be seen; the commanding officer no doubt congratulating himself upon the destruction of O’Brien’s vessel.
“It has been said,” remarks a Machias friend of Captain O’Brien, “and is doubtless in the main true, that the proceeds of the sales of the vessels and cargoes captured by Captain John O’Brien during the Revolution, contributed to the foundation of the fortunes of many of the residents of Newburyport, into which they were brought.” Captain O’Brien, upon delivering the captured prizes at the wharves or out in the harbor, would say: “Here, boys, you take care of these, and I’ll go out for more.” He evidently did not care so much for money as he did for the opportunity of seeing the British flag come down.
“He had a heart as big as an ox,” is the estimate of Captain O’Brien given by those well qualified to judge in the matter.