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In two or three letters written by Hale to his brothers in the earlier part of the summer, he mentions some hostile movements, but there are no indications that he was engaged in any of them. He seems not to have been in the battle of Long Island or a participant in the famous retreat of Washington across the East River, from Brooklyn, at the close of August. He was among the troops that remained in New York when the British invaded Long Island (for he was sick at that time), and joined the retreating forces in their march toward Harlem Heights early in September. He first appears after that movement in the presence of Washington, at the house of the opulent Quaker merchant, Robert Murray, on Murray Hill, to receive instructions for the performance of an important mission. What was the nature of that mission? Let us see:

The American army on Manhattan Island was in a most perilous condition after the retreat from Long Island. It was fearfully demoralized, and seemed to be on the point of dissolution. Despair had taken possession of the minds of the militia. They deserted by companies and even by regiments. Impatient of restraint, insubordination everywhere prevailed. The soldiers clamored for pay; the money-chest was empty. They clamored for clothing and blankets, as cold weather was approaching; the commissary could not respond. One third of the men were without tents, and one fourth of them were on the sick-roll. Only fourteen thousand men were fit for duty, and these were scattered in detachments lying between each extremity of the island, a distance of a dozen miles or more.