ca. 1737–April 1800
Gregory was commissioned lieutenant colonel in September 1775 and promoted to colonel seven months later. He served as a member of the Safety Committee of the Edenton District and was named by the Provincial Congress to procure arms in Pasquotank County and to take charge of Tory property. The General Assembly in July 1777 named him to a committee to establish a courthouse and other public buildings for the new county of Camden in which his extensive land holdings now lay. Soon after the Assembly elected him a brigadier general on 12 May 1779, he joined General Jethro Sumner at Yadkin Ford near Salisbury. At the Battle of Camden Gregory's men "fought with desperation" but were abandoned by others and outnumbered. The general was wounded in the battle and his horse was shot from under him. Cornwallis's report erroneously recorded the death of Gregory. Although he was engaged in military action in Piedmont North Carolina and upcountry South Carolina, he corresponded with governors Richard Caswell, Thomas Burke, and Alexander Martin.
In March and April 1781, Gregory and his troops were charged with protecting northeastern North Carolina from a possible British attack from their bases in Virginia. The militia made several forays in the direction of the enemy. During an idle evening in camp, a British officer, for amusement, wrote a letter to which he signed General Gregory's name. The text of the fanciful letter contained the suggestion that American forces might be betrayed to the British. The next morning the British abandoned their camp and the fictitious letter was left behind. Found soon afterward by Americans who knew nothing of its origin, it was assumed to be authentic. This discovery created a sensation and Gregory, charged with treason, was about to be court-martialed. Hearing of Gregory's predicament, the officer who had written the letter sent the Americans a full account of his role in the affair and expressed complete confidence in the loyalty of General Gregory to his country. This, of course, ended the charges, but Gregory was forever after deeply resentful of the doubt expressed at that time as to his patriotism.
Gregory represented Camden County in the North Carolina House of Commons in 1780–81 and in the senate for ten terms between 1782 and 1795. In 1782 he was named a trustee of Smith Academy in Edenton, and in 1789 he became a trustee of the Currituck Seminary of Learning. As a delegate to the constitutional conventions of 1788 and 1789, he was active as a Federalist. In 1787 and 1788 he served as a commissioner to promote navigation on Albemarle Sound. As customs collector for the District of Camden in 1793, he seized a schooner for improperly importing goods.
Gregory's first wife may have been a daughter of Caleb Sawyer; his second wife was Sarah Lamb. His children were William, Isaac, Mary, Sarah, Penelope, and Harriett. He was buried on his plantation, Fairfax (now often called Fairfield), in Camden County. The handsome, three-story brick house, dating from the 1740s, is still standing although not in good condition.