On this day 250 years ago before dawn in New York, 240 men from two Connecticut regiments of the Continental Army and New York Militia commanded by Lt. Col. Michael Jackson of Massachusetts and other officers who volunteered for the mission conducted an unsuccessful raid on the British outpost on Montresor’s Island (now Randall’s Island — part of the Borough of Manhattan in the City of New York). Through a series of mishaps — flawed intelligence about the strength of the British position on the island, an American sentry’s mistaken warning shot, and cowardice of one or more of the American officers — instead of surprising the 100 British soldiers on the island as planned, the lead American boat was ambushed by the British immediately after landing and the remaining three boats fled.

The Americans suffered at least 20 casualties but the British had only two men killed and six wounded. Major Thomas Henley, a Captain Hubbart, and at least two other soldiers were killed, and Maj. Moses Hatfield (or Hetfield) of the Orange County, New York Militia, Privates David Spencer and Matthias Button of the 8th Connecticut and 11 other soldiers were captured. Hatfield would be exchanged two years later and continue in service through the end of the War, but enlisted men captured by the British in New York suffered under torturous conditions and most did not survive. Lt. Col. Jackson was struck by musket fire in the leg, shattering the bone into more than thirty fragments and crippling him for life. Nevertheless, he continued in Service through the remainder of the War rising to the rank of brigadier general, but was “very lame & unfit for Duty” because of his wounds, and served only in administrative roles and never again held an active field command.

Sources: https://allthingsliberty.com/2019/04/fiasco-the-disastrous-raid-on-montresors-island/; https://revolutionarywarjournal.com/forgotten-patriots/; https://www.founderoftheday.com/founder-of-the-day/michael-jackson; https://www.myrevolutionarywar.com/battles/1776-skirmish/; https://www.wikitree.com/wiki/Hatfield-3825