[2] He was the Federalist nominee for the 5th congressional district in 1798, losing to Democratic-Republican incumbent Samuel Smith.
[3] Winchester received a recess appointment from President John Adams on October 31, 1799, to a seat on the United States District Court for the District of Maryland vacated by Judge William Paca.
He was nominated to the same position by President Adams on December 5, 1799.
He was confirmed by the United States Senate on December 10, 1799, and received his commission the same day.
His service terminated on April 5, 1806, due to his death in Shawan, Maryland.