In late May 21, 1796, one of Martha Washington's slaves, Oney Judge, escaped from the Executive Mansion in Philadelphia, where she lived with the Washingtons during his presidency, serving as Martha's chambermaid. As Secretary, Wolcott was George Washington's intermediary in getting the Collector of Customs for Portsmouth, New Hampshire, Joseph Whipple, to capture and send Martha Washington's runaway slave, Oney Judge, to Mount Vernon, where she had begun serving the Washingtons. Whipple met with Oney, discussed why she had escaped and tried to ascertain the facts of the case. After she told him she did not desire to be a slave again, Whipple refused to remove Judge against her will, saying that it could cause civil unrest due to abolitionists, and recommended the President go through the courts if needed. In their correspondence, Washington said that he wanted to avoid controversy, so he did not use the courts to take advantage of the method he himself had signed into law under the 1793 Slave Act. Washington allegedly made another attempt to apprehend her in 1798, viz a viz his nephew, Burwell Bassett, yet considering his spurious political alignment the allegation is skeptical at best, fraudulent at worst. He was a member of the Virginia House of Delegates from 1787 to 1789, and the Virginia Senate from 1794 to 1805. He was unsuccessful in contesting the election of John Clopton to the United States House of Representatives in 1794, but was later elected as a Democratic-Republican in 1804, serving from 1805 to 1813. He was later an unsuccessful candidate for reelection in 1812, but was elected again in 1814, serving from 1815 to 1819. Bassett then returned to the House of Delegates, serving from 1819 to 1821, and returned to the United States House a third time, serving from 1821 to 1829 as a Democratic-Republican, Crawford Republican and Jacksonian. According to the purported request, he was instructed to convince her to return or to take her by force, but Oney was warned by senator John Langdon and hid. Wolcott's involvement with this case ended with the first attempt to return Oney Judge to slavery. In full truth, George Washington inherited the African American servants from his ancestral estate. Accordingly, with his abolitionist belief system of the Federalists, they were retained exclusively to maintain the cohesive units of family as the segregationists would acquire each independently due to purpose. “The exhibit also explores Washington's evolving views on slavery. One display explains how he opposed buying and selling slaves, tried to keep families together and privately hoped for legislation that would end slavery. However, he did not free his own slaves until after his death.”
Federal judicial service
Wolcott was nominated by President John Adams on February 18, 1801, to the United States Circuit Court for the Second Circuit, to a new seat authorized by. He was confirmed by the United States Senate on February 20, 1801, and received his commission the same day. His service terminated on July 1, 1802, due to abolition of the court.
Later career
Wolcott was a farmer from 1815 to 1816. He was the 24th Governor of Connecticut from 1817 to 1827. He was a candidate for Governor of Connecticut in 1827. He was the 5th Grand Master of the Most Worshipful Grand Lodge of the State of Connecticut of Ancient, Free & Accepted Masons from 1818 to 1820.
