Of the boyhood of John O’Brien, in Scarboro, little has been preserved. He must, however, have been different from other boys of his age, if he did not, living in such close proximity to the water, acquire a fondness for it. This much is certainly known; that in the autumn of 1765, when the robust boy was about fifteen years of age, the entire family, comprising Mr. and Mrs. O’Brien and six sons and three daughters, removed to Machias, on the southeasterly coast of Maine; the father and two eldest sons having been down there on a prospecting trip, in a sailing vessel, during the previous year.

From the arrival of the lad, John O’Brien, in Machias, until the breaking out of the Revolution, little or nothing is certainly known concerning him. That he attended school, for a time, at least; and that he engaged in the usual sports of lusty boyhood, including swimming, fishing and boating, may be safely inferred. Neither is it a far-fetched conclusion, that, on attaining to a suitable age, he assisted his father, and two eldest brothers, Jeremiah and Gideon, in the sawmills erected by them in Dublin, as the southern village of Machias was early named, and by which it is still known.

The Machias River, which separates the northern and southern villages of Machias, empties into Machias Bay, about four miles to the southeastward of the town; and the river, as far inland as Machias, is navigable for large vessels. Machias, therefore, was, and is a seaport town; and vessels of various kinds were constantly arriving and leaving. Machias early became the shiretown of Lincoln County, now Washington County, and hence was a place of considerable importance. In the light of these facts it is not surprising that most of Morris O’Brien’s “six strapping boys” were, in early life, at least, seafaring men; for from their peculiar environment they naturally acquired a taste for that sort of employment. John O’Brien, as will be seen, devoted himself, in later life, exclusively to commercial and mercantile pursuits, with excellent success; indeed, had the acquisition of “filthy lucre” been his chief ambition, he might easily have become one of the wealthiest men of his time.

It is in connection with the outbreak of the Revolution that the subject of this sketch first comes into public notice as a citizen and an ardent patriot; and as the war progressed, his fame as a privateersman increased. His achievements as a privateersman have never received the publicity they unquestionably deserve; and it will be the aim of this sketch to acquaint the American reading people, so far as can be done in the limited space allowed, with the story of the truly romantic career of this hitherto “unsung hero” of New England.

John O’Brien, at the outbreak of the Revolution, was about twenty-four years of age. He was fully six feet in height; and must have weighed at that time not far from one hundred and seventy-five pounds. That he was well endowed with force of character was amply demonstrated at the very opening of his public career; as an illustration of which it may be said that none was more resolutely opposed to, nor more fearlessly outspoken against the repeated acts of tyranny of the mother country, than he. He was a member of the first Committee of Safety appointed in Machias, after the issuance of the proclamation of the Provincial Congress of Massachusetts, authorizing and requiring preparations and efforts to be made incident to a state of hostility.

At the first recorded gathering of the Machias patriots, held in the east room of the Burnham Tavern,[[21]] John O’Brien was present, and gave his hearty assent to the proposition for the erection of a liberty pole in the village, as a symbol of the freedom, for the achievement of which the people of that then isolated frontier town were willing, if need be, to sacrifice their fortunes and their lives. In procuring, and afterward raising the liberty pole, young O’Brien played a unique and conspicuous part.

When Captain Moore, the gallant young Irishman commanding the British armed schooner “Margaretta,” then lying at anchor in the Machias River, came on shore, and demanded that the liberty pole be taken down, John O’Brien, on behalf of the inhabitants, defiantly refused to accede to the peremptory demand of the King’s officer, The following conversation[[22]] is said to have taken place:

“Who erected this pole?” inquired Captain Moore, as he came ashore from the “Margaretta”; to which the staunch Machias patriot, John O’Brien, replied:

“That pole, sir, was erected by the unanimous approval of the people of Machias.”

“Well, sir,” said Moore, “with or without their approval, it is my duty to declare it must come down.”