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Capt. Henry Prentiss

Interesting bits of information about Capt. Henry Prentiss.

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Portrait painted in 1791 by a fellow-collegian.
Owned by his daughter, Eliza F. Prentiss in 1852 (I wonder where it is now?).
Our copy is from page 110 of the 1852 edition of Binney's Prentice Genealogy.


History of the Military company of the Massachusetts, now called the Ancient and honorable artillery company of Massachusetts. 1637-1888, Volume 2 p.214-215 (Google books)

Henry Prentiss (1786), merchant, of Boston, son of Rev. Joshua and Mary Prentiss, was born March 7, 1749, in Holliston, Mass., where his father was pastor of the church for forty-five years. He married in 1775, Ruth, daughter of Jonathan Freeman, of Boston. Henry Prentiss (1786) was a spectator of the scene in State Street, March 5, 1770, when the British soldiers killed five persons and wounded several others. On the 7th of March, Henry Prentiss (1786) wrote a long letter to his father describing the scene and the events which followed it. The letter is printed entire in Mr. Drake's "History of Middlesex County," Vol. I., pages 472, 473. Henry Prentiss (1786) is recorded in the traditional number of those who took part in the "tea" episode of 1773. He was a member of the Masonic Fraternity, having been initiated in The Massachusetts Lodge of Boston, Feb. 19, 1789.

Mr. Prentiss (1786) was a captain in the Revolutionary War, serving under Gen. Washington at Cambridge and Long Island; also was at the crossing of the Delaware, and at the battle of Trenton. On his return from active service he was an overseer of the poor, in Boston, three years, 1784-7, a sea captain in 1789, and afterward a merchant in Boston. Henry Prentiss (1786), with his brother Appleton, was the first to introduce the art of printing calico in New England, producing a coarse blue and red article on India cotton. A specimen of it was exhibited by the late Abbot Lawrence at a fair in the city of Washington, many years ago, as a contrast to the improved prints of later days. The print manufactory was on the corner of Cambridge and Buttolph streets. He was largely interested in the West Boston Bridge, sometimes called "Cambridge Bridge," and with Mungo Mackay superintended the construction of it. He died in Medfield Mass., Aug. 31, 1821, and his remains were placed in King's Chapel Burial Ground. He resided for many years in a stone house on the south side of Hanover Street, near Elm Street, the former residence of Benjamin Hallowell, comptroller of customs, which was ransacked by the patriots at the time Gov. Hutchinson's house was visited by them.


Drake's "History of Middlesex County," Vol. I., pages 472, 473 (Google books)

Letter from Henry Prentiss to his father, Rev. Joshua Prentiss, regarding the "Boston Massacre." (Sorry about the run-on sentence and lack of paragraphs; this is how it was apparently written!)

Boston, March 7th, 1770

Honored Sir.--I take this Opportunity to acquaint you, of that most shocking & maloncolly Scene that was exhibited in this town last Monday Evening. A scene the most Tragical, of any that ever the Eyes of Americans beheld, (and I pray God they may never see the like again) to see the blood of our fellow Citizens flowing down the gutters like water I think, must make every American, look with Detestation & Abhorrence, on these blood-thirsty wretches, that were the exhibitors (The Soldiers I mean). Military power has always been extremely disagreeable to a Free and loyal people, but never so much as at this Day, when these military forces first came among us, they said they came to restore peace and harmony, is this the way, to let us three or four of our dear fellow Countrymen, shot down dead in the streets, five or six more wounded and wallowing in their blood--no, this I think is the way, to bring on an open Eruption. but I will proceed to the particulars of this Affair, in the first place, about half past nine in Evening the soldiers insulted several people that walking in the Streets, upon this, the town was alarmed by the Ringing of Bells, and crying of fire, the people in a few minutes muster'd at & about the town House (I believe I may say) several Thousands, the Captain of the Day whose name is Preston and who belongs to the 29th Reg. seeing the people gather round the Centinal at the Custom House, draw'd out Eight or Ten men & ordered them to load after which he march'd down to the Centinal, and took him of from his station, but instead of his returning to the Main Guard after he had relieved the Centinal, he holted his men, whereupon the people closed in upon them but offered no violence as I could see & I was but about two yards distance from them, in this posture they stood, tho' but a few minutes, before one of the Soldiers rec'd a blow from a Cake of ice, that some of the people sent, upon this he fir'd & immediately upon his fireing seven or Eight Gunns more were discharg'd I stood my ground, looking and laughing to see the people run; thinking, they only fir'd clear powder to scare them, but in less than a minute I was convinc'd to the Contrary, by seeing, two Men lay dead upon the Ground, one at my right Hand & the other at my left not above a Yard distant from me, as soon as they seas'd fireing, the Cap. marched his men back to the Main Guard, then I went round to sec how many were killed & soon found three dead, two more mortally wounded, who have since died, four or five more wounded but not so badly but that the Doctors are in hopes they will survive it, the Governor and Councill were immediately called together, to consider what was necessary to be done, at this Crisis, the first step was to send for Col. Dalrymple who came in a few minutes after he was sent for, he told the people that he had serv'd his Majesty twenty years & never had seen such a horrid crime before & was extreem sorry to see it now. he further said; that the Inhabitants should have all possible satisfaction & that he himself wou'd see that both Officers and Soldiers were deliver'd into the hands of Justice, upon which the, Summons was made out against the Capt. & deliver'd to the Sheriff, together with Col. Dalrymple's letter to Col. Carr, in which Letter he ordered the Col. to see that the said Cap. Preston was deliver'd into the hands of the Sheriff immediately, which order was obey'd and the Capt. bro't before the Gov. & Councill, and examined, but several witnesses appearing against him & made Oath that they heard him Command his men to fire, they committed him to Goal. this was about four o'Clock in the Morning, at ten o'clock a Tuesday in the foornoon, the Eight Soldiers were also committed to Goal, at Eleven o'Clock there was a town Meeting call'd which I believe was the fullest, that ever was known in America. in the first place they chose a committee of fifteen Gentlemen to wait upon the Gov. & Councill with a petition the purport of which was, that they would use all their Authority & Influence to get the Soldiers remov'd to the Castle. His Honor return'd an answer which was that he had no command over the troops, but that he talked with the Commanding Officer concerning a Removall, all the Officer said he would order the 29th Reg. to the Castle, and order his own Reg. to keep in Their Barracks, remove the main Guard, and have all parading stop'd, this answer was no ways Satisfactory to the enraged inhabitants, they therefore chose another Committee of Seaven Gent. to wait upon the Governor & acquaint him that nothing short of a total removal of the troops from the town wou'd satisfy the injur'd Inhabitants. the Gov. said he could not give an immediate Answer, the Committee reply'd that they would retire into the other room till his Honor was ready. after waiting sometime he call'd them in & gave them his answer in writing, the purport of which was, that he had persuaded the Commanding Officer to send both Regiments to the Castle with all possible speed this was voted Satisfactory to the Inhabitants who were then assembled, I suppose at leest three Thousand in the Old South Meeting House, after three Huzzas, the meeting was dissolved, the transactions of the 6th of March 1700 will shine bright in the Annals of America to the last ages of time.

As my time of Apprenticeship is expired I shou'd be glad you'd send me Mr Wendell's Letter wherein he has mentioned what he was to give me when my time was up. my Duty to you and Mother & love to my Brothers and Sisters Concludes me your Duty full son.

Henry Prentiss.

P.S. The Names of those persons that were killed and their occupation. Jackson a Molatto fellow. Sailor. Gray a Rope maker. Covil mate of a vessell. Munk a Boat Builder. Maverick a Lad about fifteen years of age. Wounded viz., Edw. Payne Merch. in this town shot thro his arm. Green a Taylor shot through his thigh. Patterson shot thro his arm. The Names of the Rest have slip'd my memory.

March 9th Friday Morning Yestaday Afternoon four of those unhappy persons that were shot last Monday Evening were inter'd, the procession was much the grandest of any ever seen in America. Gray's Corps went first then his Relations, then Covil and his Relations, then Maverick and his Relations & then Jackson & after Jackson the Inhabitants walk'd four a breast. I imagine to the number of three or four Thousand, & then a vast number of Carriges, they all four were buried in one grave & young Snider dug up & put with them.

severall company's of Soldiers are gone to the Castle and the Remainder embarking as fast as possible, to-morrow Night the town will be Clear of them.

ye Dutifull Son
H. Prentiss.

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